Cycling holiday villas and apartments Isle of Wight

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Isle of Wight

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355 Holiday homes

Filters applied: Cycling holidays

Travellers going to Isle of Wight are booking June dates now. Secure your holiday home today and have the perfect trip.

(12) Excellent 

13

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Beautiful” Such a beautiful chalet with lots of space. Excellent location for children as they could just play out on the green. Lovely decor and a well equipped kitchen. Cannot find any faults at all, will hope to come back again next year..  …see more

from £36 / night

£250 - £485 / week

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from £36 / night

(8) Excellent 

13

Holiday apartment in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
This lovely 2nd floor apartment in the high standard Marinus apartments has wonderful views across Shepards Marina and the Solent. The property can be accessed via a private lift or stairs. The 2 bedroom apartment is beautifully furnished to a very high standard. Withi  …see more

from £90 / night

£400 - £2300 / week

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from £90 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Characterful cottage on the Garlic Farm on the Isle of Wight. Perfectly placed for walking, cycling and family holidays. Guests enjoy a 10% discount in our renowned restaurant, use of tennis court and football pitch. 10 minutes from the beach by car.<br />Peacocks  …see more

from £175 / night

£825 - £1925 / week

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from £175 / night

(5) Excellent 

21

Bembridge holiday home let

Bembridge / Bembridge Village

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Lovely holiday home offering peace and quiet just minutes from the beach” Lovely 3-bedroomed holiday home in a quiet lane, just minutes from the beach. Very convenient with convenience store just round the corner. Would definitely recommend the prope  …see more

from £86 / night

£600 - £1250 / week

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from £86 / night

(17) Excellent 

20

Studio rental in Ventnor with golf nearby

Isle of Wight / Ventnor

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
“Perfect - Fresh and light an enjoyable holiday” Excellent location, with stunning views. Apartment well looked after, clean and tidy. A delightful holiday with all the necessary facilities. 5 Minute walk to the seaside. 5 Stars  …see more

from £80 / night

£400 - £675 / week

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from £80 / night

(9) Very Good 

13

Holiday chalet in Yaverland

Sandown / Yaverland

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Completely renovated chalet with new fitted kitchen and bathroom 32" flat screen television with rotating arm to enable you to watch TV outside chalet. Beautifully decorated giving a modern home from home styling. Sofa bed to cater for an extra person not two adul  …see more

from £100 / night

£485 / week

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from £100 / night

(38) Excellent 

34

Bungalow rental in Ryde

Ryde / Appley

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Wonderful holiday home. Couldn't ask for more.” This was the 3rd time that we've stayed at Wightsands and it was just as fabulous as always. Wightsands is a comfortable home from home which is beautifully decorated. Everything you could ever need is p  …see more

from £100 / night

£475 - £995 / week

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from £100 / night

(4) Excellent 

27

Holiday cottage rental

Freshwater / Freshwater Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Ask owner if suitable for children
Rabbit's Bothie is in the conservation area at the heart of the Tennyson Mile at Freshwater Bay. Sheltered on both sides by the soaring white cliffs of the Tennyson Heritage Coast, the bay has smugglers' caves, dramatic rocks and a sandy beach at low tide.<  …see more

from £72 / night

£360 - £560 / week

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from £72 / night

(9) Excellent 

21

Shanklin holiday studio rental

Isle of Wight / Shanklin

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Car not necessary
“Excellent” very comfortable room, very clean, and all you need for a great stay. thank you. will stay again. Location perfect.  …see more

from £45 / night

£230 - £585 / week

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from £45 / night

(12) Excellent 

16

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“A Nice relaxing holiday” We had a fabulous 2 weeks stay at brambles chine The bungalow is well equipped and we would recommend a holiday there to everyone you get a lovely view of the needles and it's so peaceful and quiet The island is beautiful  …see more

from £40 / night

£275 - £900 / week

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from £40 / night

(21) Excellent 

21

Holiday apartment with golf nearby in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Perfect holidays - nice and well equipped appartment” On arrival we immediately felt at home at Royal Marine House. 1st floor appartment is well equipped with washing machine, dishwasher, TV/DVD and of course WIFI. We loved the view from the windows  …see more

from £80 / night

£400 - £790 / week

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from £80 / night

(8) Excellent 

14

Brighstone Bay holiday caravan/mobile home rental

Brighstone / Brighstone Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Fantastic setting friendly staff, perfect for young family” Lovely little farm setting only a walk away from the pretty bay. The children loved getting up in the morning and feeding the goats, chickens, ducks etc and then watching all of the animals  …see more

from £74 / night

£445 - £1200 / week

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from £74 / night

(39) Excellent 

32

Holiday cottage rental

Isle of Wight / Shanklin

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“This is a Gem and ticks all the boxes!” This is an immaculately clean establishment offering the choice of both B&B and self catering. It is in a great position just a few minutes walk to the beach in one direction and the town in the other. It is in  …see more

from £65 / night

£450 - £695 / week

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from £65 / night

(2) Excellent 

21

Holiday chalet rental

Isle of Wight / Seaview

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
For seaside holidays at their best!  …see more

from £43 / night

£232 - £665 / week

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from £43 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Enjoy a unique farm holiday at the Garlic Farm on the Isle of Wight. Peaceful, beautiful location close to footpaths and cycle ways. 10 minutes from the beach and most other attractions. Tennis court, football pitch and restaurant on site. Dogs welcome by arrangement.&l  …see more

from £145 / night

£675 - £1310 / week

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from £145 / night

(3) Excellent 

12

Holiday apartment in Cowes

Cowes / West Cowes

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
With its off-road parking & flexible layout with 1 bathroom, 1 en suite shower room & 1 cloakroom this property is well suited for families, small groups & corporate bookings.<br />This property is part of the Cowes Holiday Homes portfolio where good  …see more

from £75 / night

£350 - £1600 / week

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from £75 / night

(12) Very Good 

20

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
“Peaceful and beautiful!” It was a perfect escape from the hustle and bustle of London to stay at his spotless and well equipped bungalow at the Isle of Whight. We were given detailed information how to reach the bungalow and I really appreciated the o  …see more

from £38 / night

£260 - £560 / week

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from £38 / night

(5) Excellent 

11

Holiday chalet in Freshwater

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Excellent stay and location” A fabulous chalet with fantastic mod cons, a lovely welcome basket greeted us which was lovely. The chalet was great as was the location, the children enjoyed playing football on the field and climbing frames. The Isle of  …see more

from £39 / night

£275 - £595 / week

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from £39 / night

(16) Excellent 

24

Home rental in Ventnor with golf nearby

Isle of Wight / Ventnor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.75 km
  • Suitable for children age 5+
“Lovely cosy comfortable property, well presented and situated with sea views!” Stayed between Christmas and New Year during a very wet spell, but the property was warm, cosy and welcoming. Large property ideal for a family or group of friends. Proper  …see more

from £165 / night

£750 - £1200 / week

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from £165 / night

(2) Very Good 

21

Holiday home with golf nearby in Ryde

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Westridge House is a one of the most exclusive homes on the island comfortably sleeping up to 10 people. The house holds 5 bedrooms, consisting of 3 double bedrooms and 2 twin bedrooms. Stunning garden, lawns and swimming pool found on the outskirts of Ryde and Seaview.  …see more

from £600 / night

£1995 - £4695 / week

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from £600 / night

(9) Excellent 

23

Cowes holiday caravan/mobile home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
Newly refurbished for 2016. Modern 3 bedroom caravan with 1 double bedroom, 2 twin bedrooms and pull out in lounge area. Full central heating and double glazing throughout. Shower room, and additional separate WC. Caravan facilities include fully equipped kitchen with i  …see more

from £70 / night

£365 - £750 / week

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from £70 / night

(18) Excellent 

24

Holiday caravan/mobile home in Bembridge

Isle of Wight / Bembridge

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“An idyllic and picturesque holiday destination” This was our first time in a static caravan and so were a little unsure as to just what to expect however we were pleasantly surprised upon our initial arrival at the holiday park and also upon entering  …see more

from £100 / night

£350 - £650 / week

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from £100 / night

(13) Excellent 

17

Apartment letting in Bembridge

Bembridge / St Helens, Bembridge

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Such a lovely place to spend a week... or longer!” My girlfriend and I spent a week here during Wimbledon week and were blown away by how lovely the apartment and St Helen's was. Everything about the place was better than we could have dreamed of - th  …see more

from £45 / night

£225 - £399 / week

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from £45 / night

(23) Very Good 

22

Cowes holiday cottage rental

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“A lovely terrace cottage near the centre of Cowes” A very comfy cottage with a very well spec'ed out kitchen and lovely shower-wash room. Full SkyTV and wireless broadband access. The landlords communication was very clear, concise and timely.  …see more

from £100 / night

£600 - £1300 / week

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from £100 / night

(1) Excellent 

24

Holiday home in Cowes

Cowes / West Cowes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
Amazing property for up to 10 that sits just back from the waterfront and has fantastic views up and down the River Medina and to the Solent beyond from the large roof terrace - an excellent place to entertain or sit and watch the world go by. 5 bedrooms & 4 bathro  …see more

from £200 / night

£1400 - £5500 / week

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from £200 / night

(9) Excellent 

20

Holiday home with golf nearby in Cowes

Cowes / West Cowes

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Lovely sailing themed house in great location” Stylish decor, very comfy bedrooms and all the domestic equipment that was needed was there along with some nice Jazz CDs! Good location with teenagers as able to walk into main street of Cowes within  …see more

from £100 / night

£700 / week

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from £100 / night

(14) Excellent 

24

Holiday penthouse with golf nearby in Cowes

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
“Beautiful apartment” Beautiful apartment, very spacious and well located. We would use is again. The balcony and view of the Solent is excellent  …see more

from £175 / night

£875 - £3125 / week

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from £175 / night

(1) Very Good 

18

Bembridge holiday home rental

Bembridge / Bembridge Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Beach, Bembridge, 3 bedrooms,  …see more

from £115 / night

£500 - £1190 / week

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from £115 / night

(12) Excellent 

28

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“High quality, beautifully appointed holiday barn in a peaceful location.” The barn is in great location which leaves you close to any of the islands attractions or towns. It is beautifully appointed throughout with the bonus of a hot tub in the shared  …see more

from £130 / night

£580 - £1495 / week

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from £130 / night

(1) Excellent 

14

Shanklin holiday home rental

Shanklin / Old Village

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary
DISCOUNT APPLIED TO SEPTEMBER 2016 RATES. You can book for 5 nights or more from £534. The cottage has been advertised for 2016 following a break, discount rate already applied. Percy cottage (Self-catering. Sleeps 4 in total. (2 bedrooms) is nestled in the pi  …see more

from £75 / night

£525 / week

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from £75 / night

(7) Excellent 

23

Holiday home rental

Isle of Wight / Wootton Bridge

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly
Grange Farm Self Catering, location is very peaceful,perfect for walkers,cyclists,surrounded by wild life including Red squirrels and wild birds can be seen through patio doors in the breakfast room.Visit Britain 4 star highly recommded.Beeches, pub,Farm shop close by.  …see more

from £161 / night

£1125 / week

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from £161 / night

18

Niton holiday home rental

Isle of Wight / Niton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Woodington is an attractive Victorian property in an idyllic setting with breathtaking cliff views. Providing spacious accommodation it is well presented throughout, with four double bedrooms and one twin bedroom. The family bathroom comprises of bath, wash hand basin w  …see more

from £220 / night

£875 - £2025 / week

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from £220 / night

(6) Excellent 

10

Holiday barn in Shorwell

Shorwell / Billingham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
The new properties have been fitted out extremely tastefully with all the mod cons including wood burner stoves for those chilly evenings, loadsa logs available ! At the property there is also secure storage for bikes, kayaks & also wash down & workshop facili  …see more

from £70 / night

£450 / week

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from £70 / night

(3) Excellent 

24

Holiday home in Bonchurch

Isle of Wight / Bonchurch

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
“Absolutely fantastic” We stayed at Garden House during the October half term and thoroughly enjoyed it, a perfect home away from home. Well placed near Ventnor and Shanklin (our favourites on the Island), and near lots of amenities. The beds were the  …see more

from £115 / night

£805 / week

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from £115 / night

(10) Very Good 

27

Holiday cottage letting

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Whether you are looking for a family beach holiday where you can forget the car and just chill in the garden or rock pool at the beach, or plan a walking, or cycling holiday exploring the island, Drayton Cottage is an ideal base - safe, secure and warm with free wifi.  …see more

from £100 / night

£350 - £800 / week

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from £100 / night

(30) Excellent 

32

Holiday apartment in Shanklin

Shanklin / Luccombe Village

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
Contemporary designed top floor flat with 2 bedroom 2 compact shower/wcs in a detached cliffside residence with parking on the edge of Shanklin, on a spectacular stretch of cliffs. 10 min walk down to the beach, secluded garden. Fully equipped open plan kitchen.<br  …see more

from £80 / night

£560 / week

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from £80 / night

(8) Excellent 

22

Cowes holiday home rental

Cowes / West Cowes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.18 km
  • Child friendly
“Christmas in Cowes” Great house. We were a group of 9 adults and 5 children all 2 and under. This house was the perfect place to spend christmas, plenty of room and a great kitchen with everything you need including a stocked pantry, which is always h  …see more

from £295 / night

£2065 / week

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from £295 / night

(9) Excellent 

14

Home rental in Ryde with golf nearby

Isle of Wight / Ryde

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Child friendly
“A lovely place to stay” We had a very nice stay at the Auction House it was the best place we have stayed in during our travels in all our 55 years of married life. It we well equipted spotlessly clean and very comfortalble, The owners were very hel  …see more

from £75 / night

£600 - £975 / week

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from £75 / night

22

Holiday cottage in Newchurch

Sandown / Newchurch

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Tennis court, football pitch, table tennis - Discounted ferry crossings available  …see more

from £120 / night

£575 - £1275 / week

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from £120 / night

(3) Excellent 

18

Home rental in Newport

Isle of Wight / Newport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Child friendly
This is an ideal retreat from the pressures of work, in civilised and comfortable surroundings. There are country walks and foodie pubs within easy reach and lots of local history and interesting geology. There are old railway lines as cycle paths and one still working!  …see more

from £80 / night

£245 / week

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from £80 / night