Walking holiday villas and apartments Isle of Wight | Holiday Lettings

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Isle of Wight

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395 Holiday homes

Filters applied: Walking holidays (395)

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

(28) Excellent 

26

Holiday caravan/mobile home with shared pool in Thorness Bay

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“A charming experience” The Salisbury was a wonderful place to stay, it was well equipped with utensils, tea equipment and more. The living area was great with sky tv and a charming little electric fire place which gives the property great character.  …see more

from £65 / night

£375 - £865 / week

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from £65 / night

(14) Excellent 

23

Holiday home in Ryde

Isle of Wight / Ryde

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“A quaint cottage in an idyllic location” This listed quirky former coast guards cottage is an ideal bolt hole for all. All rooms offer luxury 5 star accommodation, with all mod cons thrown in with the rental price. Its central location offers the  …see more

from £54 / night

£375 - £800 / week

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from £54 / night

(21) Excellent 

25

Gurnard holiday home rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Perfect hassle-free family getaway. Built-in garden,beach and views!” This is a beautifully presented house. Buckets and spades and teddies awaited the children, as well as cakes for all of us and wine for the grown-ups. The garden suited all needs fr  …see more

from £200 / night

£900 - £1750 / week

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from £200 / night

(27) Excellent 

17

Holiday apartment with golf nearby in Alverstone Garden Village

Sandown / Alverstone Garden Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“A fab holiday in a great place” The apartment was very well maintained and the welcome basket is a nice touch. The beach and pier are within easy reach, only a short walk to both which makes the apartments location ideal. The beds are very comfy and t  …see more

from £46 / night

£265 - £690 / week

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from £46 / night

(18) Very Good 

16

Holiday cottage in Ventnor

Isle of Wight / Ventnor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“An absolutely beautiful cottage with fabulous sea view” We arrived on the day of the big snow so had the added benefit for the first day of a winters view. The cottage was cosy and warm and so beautifully decorated that we didn't feel the need to go o  …see more

from £70 / night

£490 - £880 / week

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from £70 / night

(7) Very Good 

35

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Details to be aware of” Stable Cottage is in a lovely location and is well presented, clean and modern but has a few surprising omissions such as a microwave, tumble dryer, iron and ironing board although some of these are available in a shared laundr  …see more

from £10 / night

£1090 - £1990 / week

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from £10 / night

(13) Excellent 

20

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“The stay is worth repeating” We had a cozy stay in this little cottage. As a couple very good. Bedroom was a bit cold, due to the gale blowing at night with freezing temperaturers and snow. We adviced the owners to make a second door outside to hang t  …see more

from £100 / night

£550 - £790 / week

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from £100 / night

(23) Excellent 

23

Holiday home in Ventnor

Isle of Wight / Ventnor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“great location. Great views.” The Perch provided myself, husband small child and mother in law with a comfortable and homely stay. The beds were comfortable and the rooms airy. The kitchen provided everything we needed and the garden although small h  …see more

from £150 / night

£495 - £895 / week

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from £150 / night

(29) Excellent 

45

Holiday cottage rental

Ventnor / St Lawrence, Ventnor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Absolutely beautiful cottage to spend a holiday!” This cottage is a stunning place to have a holiday. It had a real home from home feel with everything in the cottage one would need. Harry the Golden Retriever enjoyed it too having so much space to  …see more

from £150 / night

£525 - £1345 / week

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from £150 / night

(7) Excellent 

17

Cottage rental in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Fabulous place to stay and really helpful owners!” Just returned from a two week stay at the delightful Valerian Cottage with my wife and daughters (aged 6 and 4). The cottage is beautifully presented and extremely comfortable - more like a proper hom  …see more

from £80 / night

£450 - £950 / week

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from £80 / night

(4) Very Good 

21

Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“FABULOUS LOCATION” This was our second visit to Eliabeth House and we would hapily return there because the location is perfect, being close to both the sea and town centre. The views of the sea are brilliant. I spent most of my time there watching  …see more

from £50 / night

£350 - £795 / week

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from £50 / night

(16) Excellent 

13

Brighstone holiday cottage rental

Isle of Wight / Brighstone

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 km
  • Private garden
“Wonderful cottage for 2” The cottage is a wonderful place for a completely relaxing break. It was impeccably clean and very well equipped. Vanessa and Glyn were very welcoming and informative both about the cottage and local area. We were incredibl  …see more

from £63 / night

£315 - £585 / week

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from £63 / night

(17) Excellent 

24

Holiday cottage in Wootton Bridge

Isle of Wight / Wootton Bridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Lovely property” Had a great week at kipper cottage, cant wait to get back next year. Boat house was a real treat. House was clean and tidy. Lovely quite spot  …see more

from £135 / night

£695 - £1395 / week

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from £135 / night

(16) Excellent 

36

Holiday cottage rental

Isle of Wight / Bonchurch

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“A perfect choice” A delightful cottage, from which we hosted our daughter's wedding at East Dene. We couldn't have picked a better location, helped by superb weather, which enhanced this gem of a property even more.  …see more

from £90 / night

£450 - £1960 / week

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from £90 / night

(17) Excellent 

23

Seaview holiday home rental

Isle of Wight / Seaview

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“coastal seclusion” I stayed at Lebrel Lodge with friends for a winter weekend - I think there were about seven of us, mostly couples. It was extremely well appointed and immaculately clean. The weekend was a typical English winter one and so we someti  …see more

from £150 / night

£1045 - £1495 / week

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from £150 / night

(14) Excellent 

10

Holiday cottage accommodation

Isle of Wight / Bembridge

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Highly recommended!! Gorgeous house. We want to live there.” A beautiful cottage that's deceptively large. 1 double bedroom downstairs, 1 double and a huge twin bedroom upstairs. Large downstairs wet room and a family bathroom upstairs. Kitchen is ve  …see more

from £72 / night

£500 - £900 / week

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from £72 / night

(12) Excellent 

33

Holiday home with golf nearby in Seaview

Isle of Wight / Seaview

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Exceeded my expectations” Myself and my family,absolutely loved our time spent at the Lobsters Pot, it was terrific. We couldn't fault a thing, which is rare. My little Granddaughter loved the garden, and the horses in the field too. We would certain  …see more

from £85 / night

£595 - £999 / week

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from £85 / night

(20) Very Good 

20

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“A great place to start and end each day” This little chalet was a great place to lay our heads at the end of each long day exploring the island. It very quickly became "home". It was much better equipped than I had expected, with lots of little extras  …see more

from £35 / night

£225 - £475 / week

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from £35 / night

(7) Excellent 

22

Holiday cottage in Brighstone

Isle of Wight / Brighstone

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Brighstone has a church, pub, restaurant, doctor's surgery, newsagent, grocery shop (including Post Office),  …see more

from £99 / night

£345 - £785 / week

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from £99 / night

(9) Excellent 

18

Sandown holiday apartment rental

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
King size bed in bedroom 1 & twin single beds in bedroom 2.  …see more

from £70 / night

£300 - £800 / week

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from £70 / night

(13) Excellent 

12

Holiday apartment with golf nearby in Ryde

Ryde / Appley

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Mrs” Perfect flat in ideal location bring only 8 minutes from Ryde ferry terminal. It's light airy and comfortable . Clean and warm with everything you need. Nice welcome basket in kitchen with bread cereals and biscuits plus milk in fridge . Would re  …see more

from £52 / night

£364 / week

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from £52 / night

(11) Excellent 

20

Holiday cottage in Yarmouth

Yarmouth / Fort Victoria

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Wight Cottage is adjacent to Fort Victoria and close to the pretty harbour town of Yarmouth. The cottage has wonderful sea views from the master bedroom and from the living room, plus plenty of outside space for safe playing, barbequing with family/friends, or simply en  …see more

from £85 / night

£595 - £1245 / week

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from £85 / night

(2) Very Good 

39

Holiday cottage in Seaview

Isle of Wight / Seaview

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Whatever your Isle of Wight holiday needs, from family stays to short breaks for couples, Seaview Holidays can accommodate them all.  …see more

from £116 / night

£499 - £1015 / week

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from £116 / night

(83) Excellent 

25

Holiday cottage in Ventnor

Ventnor / Niton Undercliff

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“Fantastic cottage” We had a fabulous week at Camellia Cottage at the beginning of March. Well deserving of its gold award, this cottage is very well equipped, very clean and has a very home-from-home feel. We particularly enjoyed the resident wi  …see more

from £120 / night

£570 - £1475 / week

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from £120 / night

(22) Excellent 

16

Holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“IMMACULATE CHALET OVERLOOKING THE SEA AND CLIFFS” The chalet looked brand new and was spotlessly clean. It was in a lovely position. You could see the sea and cliffs from the settee-impressive when there was a thunderstorm and you could watch it in  …see more

from £25 / night

£195 - £550 / week

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from £25 / night

(13) Excellent 

22

St Helens holiday lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“Fantastic stay!!” We (4 adults and one baby) stayed here for a week in february and thoroughly enjoyed every minute. The accommodation was brilliant. Everything you could need was there and the place was spotless. A definite home from home. Will g  …see more

from £65 / night

£395 - £1295 / week

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from £65 / night

(61) Excellent 

20

Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
“Wished I could have stayed longer..” Thank you to Dawn and Guy for a lovely, if all too short, stay at Marina Apartments. The location was very specal, with fabulous sea views and all the amenities of Ventnor right on your doorstep, including a beach  …see more

from £75 / night

£400 - £825 / week

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from £75 / night

(14) Excellent 

27

Holiday cottage in Brading

Isle of Wight / Brading

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Had a wonderful stay - Clean and Spacious with warm welcome by Colin and Julie” Colin and Julie gave us warmest welcome and made sure we have a comfortable stay. The house was spacious, kept very tidy and had everything we needed. It was nice to have  …see more

from £85 / night

£400 - £820 / week

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from £85 / night

(13) Excellent 

15

Holiday bungalow in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
“Bungalow with fabulous views” We had a very enjoyable weeks stay in July 2016. The holiday home is spacious, very clean and comfortable. It had everything needed for the four of us except I do think it should be made clear that Gary only provides hand  …see more

from £70 / night

£495 - £995 / week

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from £70 / night

(43) Very Good 

24

Yarmouth holiday cottage rental

Yarmouth / Fort Victoria

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Wonderful place to relax and unwind” Spotted the cottage from the ferry on the crossing from Lymington (which was so easy). We had a car so only took 10 minutes to get there but it would have been possible to walk from the ferry if you were fit. Ver  …see more

from £75 / night

£395 - £1245 / week

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from £75 / night

(11) Very Good 

14

Holiday chalet with golf nearby in Yaverland

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Excelent place to stay, exactly as described” We stayed for 3 nights and enjoyed our holiday very much. The house was very clean and tidy, The beach is just 5 minutes walking distance, shops and supermarket are also located nearby, Very nice and quite  …see more

from £55 / night

£259 - £520 / week

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from £55 / night

(11) Excellent 

8

Holiday log cabin with golf nearby in Whippingham

Isle of Wight / Whippingham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Private garden
This timber built cabin makes the ideal cosy holiday retreat for two. It is well situated for exploring the whole island, and its many attractions. •The village of Whippingham is near to Queen Victoria's Osborne House, and the yachting centre of Cowes.•P  …see more

from £65 / night

£325 - £450 / week

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from £65 / night

(29) Very Good 

21

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“fabulous location” Within walking (coastal walk) distance of the lovely town of Yarmouth with its charming shops, pubs and restaurant the cottage is an ideal place to stay. Would definately recommend Saltys Restaurant and the one next to it overlookin  …see more

from £75 / night

£395 - £1245 / week

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from £75 / night

(8) Excellent 

28

Holiday home in Ventnor

Isle of Wight / Ventnor

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“Lovely stay in a brilliant house in a great location.” Large, bright house with plenty of space for our group to have a very relaxing weekend. On entry house found to be very clean & tidy, rooms nicely decorated & furnished. Good range of Bedroom opti  …see more

from £155 / night

£620 - £1440 / week

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from £155 / night

(6) Very Good 

23

Holiday cottage in Ventnor

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Very homely and comfortable” Very nice, very clean, good towels and bedding sheets. Good situation, very pretty house and Garden. Lots of nice details, detergent, coffee, tea, bread, butter, milk, chocolates, a welcome pack. No parking outside the ho  …see more

from £95 / night

£525 - £995 / week

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from £95 / night

(9) Excellent 

12

Holiday bungalow 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
“Lovely, cosy and comfortable” We had a wonderful stay at the bungalow, it was cosy and comfortable. It was in a lovely spot and it would be lovely to stay again. I would defiantly recommend it.  …see more

from £45 / night

£300 - £575 / week

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from £45 / night

(5) Excellent 

12

Holiday apartment in Ventnor

Isle of Wight / Ventnor

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Pet friendly
One bedroom, pet friendly, self catering flat, near beach, great walks, great restaurants, near shops, near public transport  …see more

from £40 / night

£200 - £260 / week

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from £40 / night

(9) Excellent 

24

Holiday manor house in Wroxall

Isle of Wight / Wroxall

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Property is well equipped, free WiFi throughout, comprehensive selection of Wii/ board games and you can even borrow a dog to walk...There is safe secure bike storage, drying room for outdoor gear and bike wash down facilities. A warm welcome awaits you!<br />Cycl  …see more

from £280 / night

£1875 - £2750 / week

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from £280 / night

(4) Excellent 

20

Holiday bungalow in Freshwater

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Wow! What a find!” I stayed in this bungalow for a week with my partner and our 11 year old daughter and it was nothing short of perfect! The location is stunning with a glorious beach only a stone's throw away where we spent every evening rock po  …see more

from £43 / night

£300 - £485 / week

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from £43 / night

(8) Excellent 

8

Holiday apartment in Wootton Bridge

Wootton Bridge / Fishbourne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
Modern, well-equipped, purpose-built apartment.Fantastic superking fourposter bed in main bedroom.Free broadband WiFi.Convenient for Ryde and NewportNear car ferry terminals at Fishbourne (1 mile) and East Cowes (3 miles)<br />Sleeps six without having to use a so  …see more

from £69 / night

£295 - £875 / week

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from £69 / night

Top Destination reviews

Luxury Cowes Penthouse
Excellent place to stay loved it

Well worth the money.... We have recommend this to our family and friends. if you have small children some of the fine ornements are only to be looked at.... The large outside area is lovly in the sunshine. … see more
&quot;TOP DECK&quot; - STUNNING SEASIDE APARTMENT
Another fantastic stay at 'Top Deck'

Top Deck has everything needed for a relaxing holiday/break in Ventnor -great location, stunning views, good facilities and a lovely welcome pack. Everything from washing-up liquid and kitchen roll to shower gel and toilet roll is also provided, mak … see more
Seaspray Chalet
Great Walks

WE had a great time. Chalet was clean and comfortably. Walking distance to sandown beaches and town.15 min by to car to Ryde. … see more
Stickey Wicket
Fantastic place

Would give it 110% so clean and tidy and peaceful. There's everything you need in the chalet. Beautiful walks and scenery Looking forward to returning there again. … see more
The Mill House
We couldn't have found a better property on the island

We were expecting a welcome pack based on the reviews we read before our arrival but it exceeded our expectations - the hot cross buns were great and the selection of Easter chocolate was a lovely surprise. We felt very much at home straight away. … see more
Luxurious Park Side Apartment - The Carisbrooke
A perfect stay in a great apartment in a great location

Lovely apartment, comfortably and beautifully fitted out in a great location: ideal for the Botanic Garden and coast walks, and equally easy to walk the other way through the park and along the coast into town for some good meals out. … see more