Houses in Glossa and Villas - Holiday Lettings - Holiday Rentals Glossa

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

429 Holiday homes

(6) Excellent 

    37

    Holiday villa with swimming pool in Glossa

    Skopelos / Glossa

    2 5 7 nights min

    • 2 bedrooms
    • sleeps 5
    • 7 nights min
    • Beach / lakeside relaxation
    • Nearest beach 3 km
    • Swimming pool

    from £147 / night

    £712 - £2,588 / week

    Book View

    Responds fast!
    avg. 59 minutes

    from £147 / night

    (10) Excellent 

      20

      Holiday villa in Glossa

      Skopelos / Glossa

      3 6 7 nights min

      • 3 bedrooms
      • sleeps 6
      • 7 nights min
      • Beach / lakeside relaxation
      • Nearest beach 0.5 km
      • Swimming pool

      from £130 / night

      £907 - £2,417 / week

      Book View

      from £130 / night

      (12) Excellent 

        28

        Villa rental in Glossa with swimming pool

        Skopelos / Glossa

        3 6 7 nights min

        • 3 bedrooms
        • sleeps 6
        • 7 nights min
        • Beach / lakeside relaxation
        • Nearest beach 3 km
        • Swimming pool

        from £114 / night

        £796 - £2,115 / week

        Book View

        from £114 / night

        (8) Excellent 

          29

          Villa rental in Glossa with swimming pool

          Skopelos / Glossa

          3 7 7 nights min

          • 3 bedrooms
          • sleeps 7
          • 7 nights min
          • Beach / lakeside relaxation
          • Nearest beach 3 km
          • Swimming pool

          from £101 / night

          £705 / week

          Book View

          Responds fast!
          avg. 59 minutes

          from £101 / night

            24

            Holiday home in Glossa

            Skopelos / Glossa

            1 2 7 nights min

            • 1 bedroom
            • sleeps 2
            • 7 nights min
            • Beach / lakeside relaxation
            • Nearest beach 0.4 km
            • Child friendly

            from £54 / night

            £374 - £705 / week

            Book View

            from £54 / night

            (6) Very Good 

              31

              Holiday cottage with swimming pool in Glossa

              Skopelos / Glossa

              1 4 min stay varies

              • 1 bedroom
              • sleeps 4
              • min stay varies
              • Beach / lakeside relaxation
              • Nearest beach 3 km
              • Swimming pool

              from £142 / night

              £994 - £1,860 / week

              Book View

              Responds fast!
              avg. 1 hour 27 minutes

              from £142 / night

              (4) Excellent 

                24

                Holiday studio in Glossa

                Skopelos / Glossa

                Studio 3 5 nights min

                • Studio
                • sleeps 3
                • 5 nights min
                • Beach / lakeside relaxation
                • Child friendly
                • Car not necessary

                from £66 / night

                £353 / week

                Book View

                Responds fast!
                avg. 1 hour 9 minutes

                from £66 / night

                (2) Excellent 

                  14

                  Glossa holiday home rental

                  Skopelos / Glossa

                  4 8 min stay varies

                  • 4 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 4 km
                  • Child friendly

                  from £98 / night

                  £637 - £686 / week

                  Book View

                  Responds fast!
                  avg. 24 minutes

                  from £98 / night

                  (3) Excellent 

                    32

                    Glossa holiday villa rental

                    Skopelos / Glossa

                    3 5 7 nights min

                    • 3 bedrooms
                    • sleeps 5
                    • 7 nights min
                    • Nearest beach 3 km
                    • Swimming pool
                    • Child friendly

                    from £222 / night

                    £846 - £1,813 / week

                    Book View

                    Responds fast!
                    avg. 1 hour 5 minutes

                    from £222 / night

                    (10) Excellent 

                      23

                      Glossa holiday villa rental

                      Skopelos / Glossa

                      3 6 7 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 7 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 3 km
                      • Swimming pool

                      from £196 / night

                      £1,469 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 54 minutes

                      from £196 / night

                      (18) Excellent 

                        15

                        Holiday villa with swimming pool in Glossa

                        Skopelos / Glossa

                        1 3 7 nights min

                        • 1 bedroom
                        • sleeps 3
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Child friendly
                        “Amazing villa, amazing view, amazing owners!” We had a truly wonderful week at the villa in Glossa. The villa owners who live next door gave us complete privacy when we wanted it but were on hand to help advise and just be downright wonderful people - we feel like we have 2 new friends! They have thought if everything in the villa and then some! The villa itself could not have a better location - on the edge of a hilltop village, walking distance from tavernas, bakeries, mini markets. Yet still it remains a quiet village with lovely people...then bustly little tavernas and cafes when the sun goes down - perfect. But what can't be got across in this review is just how spectacular the view from the villa is. The villa isn't at all overlooked itself but has far reaching views of the sea and islands around Skopelos. It really is something to behold. Watching the birds and butterflies from the pool was also a joy. Thank you so much Karen and Tony - our first visit to Greece could not have been better.

                        from £139 / night

                        £974 / week

                        Book View

                        from £139 / night

                        (3) Excellent 

                          32

                          Holiday villa with swimming pool in Glossa

                          Skopelos / Glossa

                          2 4 min stay varies

                          • 2 bedrooms
                          • sleeps 4
                          • min stay varies
                          • Nearest beach 2 km
                          • Swimming pool
                          • Child friendly

                          from £101 / night

                          £705 - £1,511 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 39 minutes

                          from £101 / night

                            29

                            Glossa holiday villa rental

                            Skopelos / Glossa

                            1 5 7 nights min

                            • 1 bedroom
                            • sleeps 5
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 0.4 km
                            • Child friendly

                            from £95 / night

                            £663 - £1,396 / week

                            Book View

                            from £95 / night

                              42

                              Villa rental in Glossa

                              Skopelos / Glossa

                              3 10 7 nights min

                              • 3 bedrooms
                              • sleeps 10
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Nearest beach 0.4 km
                              • Child friendly

                              from £168 / night

                              £1,173 - £2,571 / week

                              Book View

                              from £168 / night

                                23

                                Glossa holiday home rental

                                Skopelos / Glossa

                                2 5 1 night min

                                • 2 bedrooms
                                • sleeps 5
                                • 1 night min
                                • Child friendly
                                • Pet friendly

                                from £123 / night

                                £857 / week

                                Book View

                                from £123 / night

                                (30) Excellent 

                                  25

                                  Glossa holiday villa rental

                                  Skopelos / Glossa

                                  3 6 7 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Suitable for children age 5+

                                  from £139 / night

                                  £974 - £2,176 / week

                                  Book View

                                  Responds fast!
                                  avg. 3 hours 34 minutes

                                  from £139 / night

                                  (1) Excellent 

                                    33

                                    Holiday home in Glossa

                                    Skopelos / Glossa

                                    1 3 min stay varies

                                    • 1 bedroom
                                    • sleeps 3
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0.4 km
                                    • Child friendly

                                    from £52 / night

                                    £364 - £754 / week

                                    Book View

                                    from £52 / night

                                      39

                                      Holiday villa in Glossa

                                      Skopelos / Glossa

                                      2 7 7 nights min

                                      • 2 bedrooms
                                      • sleeps 7
                                      • 7 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0.4 km
                                      • Child friendly

                                      from £144 / night

                                      £1,008 - £2,043 / week

                                      Book View

                                      from £144 / night

                                        32

                                        Holiday villa in Glossa

                                        Skopelos / Glossa

                                        1 5 min stay varies

                                        • 1 bedroom
                                        • sleeps 5
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0.4 km
                                        • Child friendly

                                        from £89 / night

                                        £621 - £1,305 / week

                                        Book View

                                        from £89 / night

                                        (31) Excellent 

                                          23

                                          Holiday villa with swimming pool in Glossa

                                          Skopelos / Glossa

                                          2 5 7 nights min

                                          • 2 bedrooms
                                          • sleeps 5
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child friendly
                                          “The most amazing villa with views that take your breath away.” We have just had a wonderful holiday in Skopelos staying at the truly magical villa Eleanora. The villa exceeded all our expectations. Set in a peaceful and rural location about 5 minutes drive from the beautiful town of Glossa, the villa was extremely comfortable, with wonderful spaces and rooms both inside and outside. The view from the verandah was magical. Having stayed in many great properties around Europe, this was definitely the best to date. We couldn't fault this place and would highly recommend others to enjoy this perfect base for a really great greek island holiday.

                                          from £164 / night

                                          £1,145 - £2,290 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 21 minutes

                                          from £164 / night

                                          (3) Excellent 

                                            43

                                            Holiday villa in Glossa

                                            Skopelos / Glossa

                                            3 11 7 nights min

                                            • 3 bedrooms
                                            • sleeps 11
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0.4 km
                                            • Child friendly

                                            from £173 / night

                                            £1,206 - £2,644 / week

                                            Book View

                                            from £173 / night

                                            (1) Excellent 

                                              30

                                              Villa letting in Glossa

                                              Skopelos / Glossa

                                              2 8 7 nights min

                                              • 2 bedrooms
                                              • sleeps 8
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.4 km
                                              • Child friendly

                                              from £119 / night

                                              £832 - £1,791 / week

                                              Book View

                                              from £119 / night

                                                13

                                                Villa rental in Glossa with swimming pool

                                                Skopelos / Glossa

                                                2 4 7 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 7 nights min
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £101 / night

                                                £705 - £2,317 / week

                                                Book View

                                                from £101 / night

                                                (4) Average 

                                                  37

                                                  Villa rental in Glossa

                                                  Skopelos / Glossa

                                                  2 8 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.4 km
                                                  • Child friendly

                                                  from £119 / night

                                                  £832 - £1,939 / week

                                                  Book View

                                                  from £119 / night

                                                    83

                                                    Glossa holiday home rental

                                                    Skopelos / Glossa

                                                    3 6 1 night min

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • 1 night min
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £61 / night

                                                    £423 / week

                                                    Book View

                                                    from £61 / night

                                                      21

                                                      Villa rental in Glossa with swimming pool

                                                      Skopelos / Glossa

                                                      3 6 7 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 7 nights min
                                                      • Nearest beach 1 km
                                                      • Swimming pool
                                                      • Child friendly

                                                      from £125 / night

                                                      £872 - £2,351 / week

                                                      Book View

                                                      from £125 / night

                                                      (4) Excellent 

                                                        20

                                                        Glossa holiday villa rental

                                                        Skopelos / Glossa

                                                        2 4 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £195 / night

                                                        £1,360 - £1,712 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 54 minutes

                                                        from £195 / night

                                                        (17) Excellent 

                                                          25

                                                          Glossa holiday cottage rental

                                                          Skopelos / Glossa

                                                          1 2 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 3 km
                                                          • Swimming pool

                                                          from £93 / night

                                                          £652 - £1,200 / week

                                                          Book View

                                                          from £93 / night

                                                          (18) Excellent 

                                                          Certificate of Excellence

                                                            21

                                                            Holiday cottage in Glossa

                                                            Skopelos / Glossa

                                                            1 4 7 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 2 km
                                                            • Ask owner if suitable for children

                                                            Certificate of Excellence

                                                            from £49 / night

                                                            £343 - £617 / week

                                                            Book View

                                                            from £49 / night

                                                            (14) Excellent 

                                                            Certificate of Excellence

                                                              25

                                                              Glossa holiday cottage rental

                                                              Skopelos / Glossa

                                                              1 2 3 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 3 nights min
                                                              • Nearest beach 2 km
                                                              • Ask owner if suitable for children

                                                              Certificate of Excellence

                                                              from £32 / night

                                                              £220 - £446 / week

                                                              Book View

                                                              from £32 / night

                                                              (1) Excellent 

                                                                19

                                                                Holiday apartment in Glossa

                                                                Skopelos / Glossa

                                                                1 3 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 3
                                                                • 3 nights min
                                                                • Nearest beach 2 km
                                                                • Child friendly

                                                                from £54 / night

                                                                £377 / week

                                                                Book View

                                                                from £54 / night

                                                                  24

                                                                  Glossa holiday villa rental

                                                                  Skopelos / Glossa

                                                                  4 10 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Nearest beach 7 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  from £192 / night

                                                                  £1,340 / week

                                                                  Book View

                                                                  from £192 / night

                                                                    16

                                                                    Holiday villa in Glossa

                                                                    Skopelos / Glossa

                                                                    2 4 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £79 / night

                                                                    £548 - £2,286 / week

                                                                    Enquire View

                                                                    from £79 / night

                                                                      12

                                                                      Glossa holiday villa rental

                                                                      Skopelos / Glossa

                                                                      2 4 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £71 / night

                                                                      £495 - £2,159 / week

                                                                      Enquire View

                                                                      from £71 / night

                                                                      Great rentals within 20 miles that match your search

                                                                      Distance approx 8.44 miles from Glossa

                                                                        29

                                                                        Katsarou holiday villa rental

                                                                        Skiathos / Katsarou

                                                                        3 6 7 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 7 nights min
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Air conditioning

                                                                        from £282 / night

                                                                        £1,974 - £3,666 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 33 minutes

                                                                        from £282 / night

                                                                        Distance approx 8.05 miles from Glossa

                                                                          24

                                                                          Holiday villa in Megali Ammos

                                                                          Skiathos / Megali Ammos

                                                                          2 5 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 5
                                                                          • min stay varies
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £131 / night

                                                                          £917 - £2,221 / week

                                                                          Book View

                                                                          from £131 / night

                                                                          Distance approx 12.99 miles from Glossa

                                                                            9

                                                                            Holiday villa with shared pool in Alonnisos Town

                                                                            Alonnisos / Alonnisos Town

                                                                            2 5 4 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 5
                                                                            • 4 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £303 / night

                                                                            £2,115 - £3,243 / week

                                                                            Book View

                                                                            from £303 / night

                                                                            Distance approx 13.03 miles from Glossa

                                                                              19

                                                                              Holiday villa in Alonnisos

                                                                              Magnesia Region / Alonnisos

                                                                              2 4 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 5 km
                                                                              • Child friendly

                                                                              from £121 / night

                                                                              £846 - £1,058 / week

                                                                              Book View

                                                                              from £121 / night

                                                                              Distance approx 13.74 miles from Glossa

                                                                              (3) Excellent 

                                                                                8

                                                                                Holiday cottage in Votsi

                                                                                Alonnisos / Votsi

                                                                                1 4 7 nights min

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • 7 nights min
                                                                                • Nearest beach 1 km
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £81 / night

                                                                                £564 / week

                                                                                Book View

                                                                                from £81 / night

                                                                                Distance approx 8.58 miles from Glossa

                                                                                  25

                                                                                  Home rental in Kanapitsa

                                                                                  Skiathos / Kanapitsa

                                                                                  6 12 1 night min

                                                                                  • 6 bedrooms
                                                                                  • sleeps 12
                                                                                  • 1 night min
                                                                                  • Child friendly

                                                                                  from £444 / night

                                                                                  £3,103 / week

                                                                                  Book View

                                                                                  from £444 / night

                                                                                  Top Destination reviews

                                                                                  Traditional Pool Villa Maria O
                                                                                  The most relaxing holiday ever

                                                                                  This was our fourth visit to Skopelos island which is beyond beautiful. Our first stay at this particular villa and also this area of the island. Very quiet and peaceful part of the island but we did visit Skopelos town as more choice for eating out. The villa itself was lovely and the views amazing. The owners of the villa were extremely helpful as were Magic Cars who we hired a Jimney Jeep from.see more
                                                                                  Dion Studio Apartment
                                                                                  A superb location 10 yards from the sea - also a lovely small & relaxed island - SUPERB!

                                                                                  The Dionysos Studios are in a superb location over looking the sea & 200 yards from the harbour of Loutraki. The island is small & very beautiful, with a typically relaxed Greek style. The tavernas & restaurants in Loutraki & Glossa (the beautiful village above) were excellent! Overall, a brilliant laid-back & relaxing holiday. Recommended!see more
                                                                                  Villa Yiali
                                                                                  A Perfect Property made a perfect holiday

                                                                                  Everything about this property was perfect. Right from booking the pre holiday help from the owners Karen and Tony was invaluable. The views are breathtaking. Glossa is a beautiful hillside village and has a range of amenities and tavernas that mean you won't have to travel far if you don't want to. Karen and Tony were a blessing throughout the stay and work hard to ensure you have everything you need without intruding on your holiday. We didn't hire a car which reduces your options but there is a very good bus service on the island which can get you to most places on the island. We have an 11 year old who loved the island and was more than happy with the pool and beaches on Skopelos. Skopelos is a real gem and it was a relaxing treat to spend a week in Glossa. We have rented many properties over the years but this tops them all for location, weather but especially the hard work put in by Karen and Tony.see more
                                                                                  Villa Eleonorae
                                                                                  AMAZING VILLA, POOL, VIEW AND ACCOMMODATION THAT EXCEEDS ALL EXPECTATIONS!

                                                                                  We stayed for a week in June. Shane the host (as many have said) is excellent and has a sound knowledge of the island...helped us with car hire, our luggage from the ferry and lots of other recommendations. The villa has a secluded location but is close enough to all the major beaches and the pretty town of Glossa and not far from the Mamma Mia beaches and sites. Fully equipped is an understatement and every possible anticipated need has been provided. It really did feel so comfortable and everyone was able to relax in it's surroundings. The grounds and villa were meticulously maintained and kept clean throughout our stay. There was a gas station and supermarket very close by and the restaurants in Glossa were so reasonable for the quality and quantity of food served. Greek hospitality is amazing anyway and we rented a boat for a day's sailing (18 of us on board) which was a highlight. Shopping in Skopelos town was fun. A car is recommended although in the evenings, we found getting to and from places with taxis also very easy. We went Diving and Shane also had some great paddle board tours on offer. The island is beautiful - we will return and will return to this villa!see more
                                                                                  Old Wine Store - romantic stone cottage with great sea views
                                                                                  Very quaint, quiet and delightfully tucked away.

                                                                                  This little Old Wine Store is an idyllic spot to have an intimate, get-away-from-it-all quiet break. The facilities are basic but adequate; you can't cook a roast dinner but who would want to? The shower is great with gushing hot water although the floor needs mopping up afterwards if you're not very careful where you spray! But the wi-fi is excellent. The sleeping area up on the mezzanine is a little cramped and can get rather warm. There is hanging space in a cupboard for several clothes and a chest of drawers. The owners/hosts are most helpful (English) and welcoming. The views down to the sea and off to the west from the two terraces are delightful. The walk into the village of Glossa is up and down a bit and around the village is up and down flights of steps if you need/want to get to different levels. There are several very good and reasonable eateries. One we found we liked was on the corner by the lower church and the bus stop, just up a few steps of the flight by the school - very home cooking, informal service and very friendly - and quite well priced. There are several other shops including supermarkets, butcher, baker, post office and gift shops. The bus service around the island and down to the harbour at Loutraki goes past all the beaches on the west coast, some accessible down a track, some right by the bus stop and runs several times a day. Costs are from 1.80 to 5 Euros -ish depending on distance. This place was well described on its website and did not disappoint. If you're seeking a quiet little gem of a hideaway, go for it!see more

                                                                                  Also consider