Cottages in Upwey and Houses – Holiday Lettings - Holiday Rentals Upwey

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950 Holiday homes

(3) Very Good 

    12

    Holiday cottage in Upwey

    Weymouth / Upwey

    1 2 min stay varies

    • 1 bedroom
    • sleeps 2
    • min stay varies
    • Beach / lakeside relaxation
    • Child friendly
    • Pet friendly

    from £86 / night

    £401 - £670 / week

    Book View

    Responds fast!
    avg. 3 hours 5 minutes

    from £86 / night

    (2) Excellent 

      12

      Cottage rental in Upwey

      Weymouth / Upwey

      1 4 3 nights min

      • 1 bedroom
      • sleeps 4
      • 3 nights min
      • Beach / lakeside relaxation
      • Nearest beach 8 km
      • Child friendly

      from £115 / night

      £682 / week

      Book View

      Responds fast!
      avg. 51 minutes

      from £115 / night

      (3) Excellent 

        12

        Holiday cottage in Upwey

        Weymouth / Upwey

        2 4 min stay varies

        • 2 bedrooms
        • sleeps 4
        • min stay varies
        • Beach / lakeside relaxation
        • Child friendly
        • Pet friendly

        from £121 / night

        £516 - £894 / week

        Book View

        Responds fast!
        avg. 3 hours 5 minutes

        from £121 / night

        (19) Very Good 

          21

          Upwey holiday cottage rental

          Weymouth / Upwey

          2 4 2 nights min

          • 2 bedrooms
          • sleeps 4
          • 2 nights min
          • Beach / lakeside relaxation
          • Nearest beach 4 km
          • Child friendly
          “The most idyllic holiday cottage” This is the second time that I have visited this gorgeous cottage. It is compact but has everything you could need for a short break. The garden is sweet and my children aged 11 and 6, love the cottage and found plenty to do in the area and have already requested to go again. Even washing up is a pleasure here - when you look out the window at the calm, rural view. Thoroughly recommend it.

          from £126 / night

          £378 - £796 / week

          Book View

          from £126 / night

          (11) Excellent 

            57

            Holiday cottage in Upwey

            Weymouth / Upwey

            4 8 3 nights min

            • 4 bedrooms
            • sleeps 8
            • 3 nights min
            • Beach / lakeside relaxation
            • Nearest beach 4 km
            • Child friendly

            from £252 / night

            £1,764 / week

            Book View

            from £252 / night

            (2) Excellent 

              32

              Holiday cottage in Upwey

              Weymouth / Upwey

              3 6 min stay varies

              • 3 bedrooms
              • sleeps 6
              • min stay varies
              • Nearest beach 5 km
              • Child friendly
              • Pet friendly

              from £101 / night

              £642 - £1,140 / week

              Book View

              Responds fast!
              avg. 1 hour 30 minutes

              from £101 / night

              (2) Excellent 

                20

                Holiday home letting

                Weymouth / Upwey

                3 6 3 nights min

                • 3 bedrooms
                • sleeps 6
                • 3 nights min
                • Child friendly
                • Pet friendly
                • Private garden

                from £125 / night

                £509 - £2,005 / week

                Enquire View

                from £125 / night

                  17

                  Holiday home in Upwey

                  Weymouth / Upwey

                  1 2 3 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 3 nights min
                  • Private garden

                  from £79 / night

                  £316 - £829 / week

                  Enquire View

                  from £79 / night

                  (2) Excellent 

                    19

                    Holiday home rental

                    Weymouth / Upwey

                    2 4 3 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 3 nights min
                    • Child friendly
                    • Private garden

                    from £117 / night

                    £450 - £1,348 / week

                    Enquire View

                    from £117 / night

                    (1) Excellent 

                      15

                      Holiday home accommodation

                      Weymouth / Upwey

                      2 4 3 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 3 nights min
                      • Child friendly
                      • Pet friendly
                      • Private garden

                      from £112 / night

                      £405 - £1,393 / week

                      Enquire View

                      from £112 / night

                        18

                        Holiday home rental

                        Weymouth / Upwey

                        2 4 3 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 3 nights min
                        • Child friendly
                        • Pet friendly
                        • Private garden

                        from £118 / night

                        £450 - £1,411 / week

                        Enquire View

                        from £118 / night

                        (1) Excellent 

                          17

                          Holiday home in Upwey

                          Weymouth / Upwey

                          3 6 3 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Child friendly
                          • Private garden

                          from £125 / night

                          £503 - £1,857 / week

                          Enquire View

                          from £125 / night

                            13

                            Upwey holiday cottage rental

                            Weymouth / Upwey

                            2 4 3 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 3 nights min
                            • Child friendly

                            from £139 / night

                            £417 - £1,174 / week

                            Enquire View

                            from £139 / night

                            (5) Excellent 

                              31

                              Holiday home in Upwey

                              Weymouth / Upwey

                              2 4 3 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 3 nights min
                              • Pet friendly
                              • Private garden

                              from £105 / night

                              £423 - £1,329 / week

                              Enquire View

                              from £105 / night

                                18

                                Holiday cottage in Upwey

                                Weymouth / Upwey

                                1 2 3 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 3 nights min
                                • Child friendly

                                from £132 / night

                                £403 - £1,011 / week

                                Enquire View

                                from £132 / night

                                Great rentals within 20 miles that match your search

                                Distance approx 5.27 miles from Upwey

                                (53) Very Good 

                                  16

                                  Holiday cottage in Wyke Regis

                                  Weymouth / Wyke Regis

                                  2 5 min stay varies

                                  • 2 bedrooms
                                  • sleeps 5
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.1 km
                                  • Child friendly

                                  from £61 / night

                                  £378 - £825 / week

                                  Book View

                                  from £61 / night

                                  Distance approx 8.47 miles from Upwey

                                  (7) Excellent 

                                  Certificate of Excellence

                                    42

                                    Holiday home in Piddlehinton

                                    Dorchester / Piddlehinton

                                    4 7 min stay varies

                                    • 4 bedrooms
                                    • sleeps 7
                                    • min stay varies
                                    • Nearest beach 20 km
                                    • Child friendly
                                    • Pet friendly

                                    Certificate of Excellence

                                    from £144 / night

                                    £1,002 / week

                                    Book View

                                    Responds fast!
                                    avg. 3 hours 1 minutes

                                    from £144 / night

                                    Distance approx 14.21 miles from Upwey

                                    (1) Excellent 

                                      20

                                      Holiday farmhouse in Winterborne Kingston

                                      Blandford Forum / Winterborne Kingston

                                      4 10 3 nights min

                                      • 4 bedrooms
                                      • sleeps 10
                                      • 3 nights min
                                      • Nearest beach 19 km
                                      • Child friendly
                                      • Private garden

                                      from £367 / night

                                      £2,565 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 8 minutes

                                      from £367 / night

                                      Distance approx 12.06 miles from Upwey

                                      (12) Excellent 

                                        19

                                        Cottage rental in Cerne Abbas

                                        Dorset / Cerne Abbas

                                        4 10 min stay varies

                                        • 4 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Nearest beach 30 km
                                        • Child friendly
                                        • Pet friendly

                                        from £171 / night

                                        £882 - £1,844 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 20 minutes

                                        from £171 / night

                                        Distance approx 15.75 miles from Upwey

                                        (54) Very Good 

                                          21

                                          Chideock holiday log cabin rental

                                          Bridport / Chideock

                                          1 3 min stay varies

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

                                          from £75 / night

                                          £516 - £596 / week

                                          Book View

                                          Responds fast!
                                          avg. 3 hours 32 minutes

                                          from £75 / night

                                          Distance approx 4.2 miles from Upwey

                                          (37) Excellent 

                                          Certificate of Excellence

                                            23

                                            Home rental in Rodwell

                                            Weymouth / Rodwell

                                            3 5 7 nights min

                                            • 3 bedrooms
                                            • sleeps 5
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0.5 km
                                            • Child friendly

                                            Certificate of Excellence

                                            from £189 / night

                                            £1,317 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 7 minutes

                                            from £189 / night

                                            Distance approx 12.67 miles from Upwey

                                            (15) Excellent 

                                              12

                                              Holiday cottage in West Milton

                                              Dorset / West Milton

                                              2 4 min stay varies

                                              • 2 bedrooms
                                              • sleeps 4
                                              • min stay varies
                                              • Nearest beach 6 km
                                              • Child friendly
                                              • Pet friendly

                                              from £81 / night

                                              £602 - £945 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 16 minutes

                                              from £81 / night

                                              Distance approx 13.33 miles from Upwey

                                              (10) Excellent 

                                                5

                                                Holiday yurt in Bridport

                                                Dorset / Bridport

                                                1 2 2 nights min

                                                • 1 bedroom
                                                • sleeps 2
                                                • 2 nights min
                                                • Nearest beach 7 km
                                                • Child friendly
                                                • Private garden

                                                from £138 / night

                                                £962 / week

                                                Book View

                                                from £138 / night

                                                Distance approx 8.35 miles from Upwey

                                                (53) Very Good 

                                                Certificate of Excellence

                                                  17

                                                  West Bexington holiday chalet rental

                                                  Dorset / West Bexington

                                                  2 6 3 nights min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 3 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.1 km
                                                  • Child friendly

                                                  Certificate of Excellence

                                                  from £81 / night

                                                  £561 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 18 minutes

                                                  from £81 / night

                                                  Distance approx 11.8 miles from Upwey

                                                  (25) Very Good 

                                                  Certificate of Excellence

                                                    32

                                                    Holiday home in West Lulworth

                                                    Dorset / West Lulworth

                                                    3 8 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 3 km
                                                    • Child friendly

                                                    Certificate of Excellence

                                                    from £207 / night

                                                    £916 - £1,924 / week

                                                    Book View

                                                    from £207 / night

                                                    Distance approx 13.61 miles from Upwey

                                                    (36) Excellent 

                                                      34

                                                      Melplash holiday cottage rental

                                                      Bridport / Melplash

                                                      3 5 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 5
                                                      • min stay varies
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 6 km
                                                      • Child friendly

                                                      from £94 / night

                                                      £403 - £1,145 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 1 hour 52 minutes

                                                      from £94 / night

                                                      Distance approx 3.52 miles from Upwey Show on Map

                                                      (3) Excellent 

                                                        10

                                                        Chickerell holiday b&b rental

                                                        Weymouth / Chickerell

                                                        1 2 1 night min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 1 night min
                                                        • Nearest beach 4 km
                                                        • Car not necessary
                                                        • Private garden

                                                        from £86 / night

                                                        £602 / week

                                                        Book View

                                                        from £86 / night

                                                        Distance approx 17.06 miles from Upwey

                                                        (6) Excellent 

                                                          19

                                                          Holiday barn in King Stag

                                                          Sherborne / King Stag

                                                          6 12 7 nights min

                                                          • 6 bedrooms
                                                          • sleeps 12
                                                          • 7 nights min
                                                          • Nearest beach 40 km
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £1,432 / night

                                                          £2,977 / week

                                                          Book View

                                                          from £1,432 / night

                                                          Distance approx 2.8 miles from Upwey Show on Map

                                                          (12) Excellent 

                                                          Certificate of Excellence

                                                            21

                                                            Holiday home in Weymouth

                                                            Dorset / Weymouth

                                                            2 4 4 nights min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 4 nights min
                                                            • Child friendly
                                                            • Car not necessary
                                                            • Private garden

                                                            Certificate of Excellence

                                                            from £138 / night

                                                            £733 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 40 minutes

                                                            from £138 / night

                                                            Distance approx 2.31 miles from Upwey Show on Map

                                                            (10) Excellent 

                                                              46

                                                              Tincleton holiday cottage rental

                                                              Dorchester / Tincleton

                                                              3 6 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 10 km
                                                              • Child friendly

                                                              from £212 / night

                                                              £773 - £1,827 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 3 hours 16 minutes

                                                              from £212 / night

                                                              Distance approx 18.52 miles from Upwey

                                                              (9) Very Good 

                                                                25

                                                                Holiday cottage in Corfe Castle

                                                                Isle of Purbeck / Corfe Castle

                                                                2 5 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 5
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 5 km
                                                                • Child friendly

                                                                from £160 / night

                                                                £624 - £1,097 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 hours 50 minutes

                                                                from £160 / night

                                                                Distance approx 16.19 miles from Upwey

                                                                (3) Excellent 

                                                                  24

                                                                  Cottage rental in Sturminster Newton

                                                                  Dorset / Sturminster Newton

                                                                  1 3 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 3
                                                                  • 3 nights min
                                                                  • Nearest beach 46 km
                                                                  • Child friendly
                                                                  • Pet friendly

                                                                  from £113 / night

                                                                  £391 / week

                                                                  Book View

                                                                  from £113 / night

                                                                  Distance approx 4.13 miles from Upwey Show on Map

                                                                    16

                                                                    Holiday home with shared pool in Chickerell

                                                                    Weymouth / Chickerell

                                                                    2 4 3 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 3 nights min
                                                                    • Swimming pool
                                                                    • Child friendly

                                                                    from £74 / night

                                                                    £422 - £1,659 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 5 minutes

                                                                    from £74 / night

                                                                    Distance approx 17.97 miles from Upwey

                                                                    (35) Excellent 

                                                                      22

                                                                      Broadwindsor holiday cottage rental

                                                                      Dorset / Broadwindsor

                                                                      2 4 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Beach / lakeside relaxation
                                                                      • Child friendly
                                                                      • Pet friendly

                                                                      from £86 / night

                                                                      £315 - £790 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 1 hour 13 minutes

                                                                      from £86 / night

                                                                      Distance approx 3.53 miles from Upwey Show on Map

                                                                        4

                                                                        Weymouth holiday b&b rental

                                                                        Dorset / Weymouth

                                                                        1 2 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 2 nights min
                                                                        • Child friendly

                                                                        from £93 / night

                                                                        £650 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 3 minutes

                                                                        from £93 / night

                                                                        Distance approx 7.91 miles from Upwey

                                                                          9

                                                                          Home rental in Bridport

                                                                          Dorset / Bridport

                                                                          3 6 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Child friendly
                                                                          • Pet friendly

                                                                          from £138 / night

                                                                          £962 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 3 hours 59 minutes

                                                                          from £138 / night

                                                                          Distance approx 15.65 miles from Upwey

                                                                            36

                                                                            Holiday cottage in Woolland

                                                                            Blandford Forum / Woolland

                                                                            2 4 1 night min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 1 night min
                                                                            • Private garden

                                                                            from £43 / night

                                                                            £301 / week

                                                                            Enquire View

                                                                            from £43 / night

                                                                            Distance approx 17.94 miles from Upwey

                                                                              14

                                                                              Holiday apartment in Alweston

                                                                              Sherborne / Alweston

                                                                              1 2 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 2 nights min
                                                                              • Pet friendly

                                                                              from £86 / night

                                                                              £602 / week

                                                                              Book View

                                                                              from £86 / night

                                                                              Distance approx 4.94 miles from Upwey Show on Map

                                                                              (1) Excellent 

                                                                                9

                                                                                Holiday b&b in Abbotsbury

                                                                                Weymouth / Abbotsbury

                                                                                2 4 2 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 4
                                                                                • 2 nights min
                                                                                • Beach / lakeside relaxation
                                                                                • Nearest beach 3 km
                                                                                • Child friendly

                                                                                from £224 / night

                                                                                £1,512 / week

                                                                                Book View

                                                                                from £224 / night

                                                                                Distance approx 13.5 miles from Upwey

                                                                                  23

                                                                                  Holiday home in Evershot

                                                                                  Dorset / Evershot

                                                                                  3 6 2 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • 2 nights min
                                                                                  • Child friendly
                                                                                  • Private garden

                                                                                  from £164 / night

                                                                                  £1,089 - £2,383 / week

                                                                                  Book View

                                                                                  from £164 / night

                                                                                  Top Destination reviews

                                                                                  The Brambles
                                                                                  Lovely cottage

                                                                                  The brambles is a lovely cottage in a lovely location, & easy to get to different places would recamend to friends … see more
                                                                                  Upwey Cottage - Weymouth
                                                                                  Cosy and comfortable

                                                                                  Enjoyed a great weekend away in this cosy and comfortable cottage, which had everything we needed for our stay. Lovely views from the windows over local countryside. Garden was quiet and secure. … see more
                                                                                  Vitality Cottage
                                                                                  Lovely cottage in quiet village close to Dorchester and Weymouth

                                                                                  We stayed for a week with teenage daughters and an elderly parent, and had a wonderful time. Very quiet (apart from Saturday night when a private party at the nearby pub continued into the small hours). We ate twice in the pub, but otherwise cooked at the cottage (after shopping at supermarkets in Dorchester and Weymouth, or the local shop at Broadwey), and found everything we needed in the well-equipped kitchen. Lovely to sit outside in the gravelled garden. Bedrooms clean and attractive, with a loft bedroom where our teenage daughters could establish their own space! Lovely location, with a footpath leading up to the top of the Ridgeway and splendid views both north over Dorchester and south towards Portland. A gentle walk down Elwell Street leads to the Wishing Well and lovely tea rooms. We were in Upwey without a car, but there is an excellent local bus service (every ten minutes for much of the day). The house was immaculate when we arrived, and the owners friendly and helpful.see more

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