Walking holiday villas and apartments Isle of Wight

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Isle of Wight

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396 Holiday homes

Filters applied: Walking holidays (396)

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

(4) Excellent 

11

Holiday home letting

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden
This spacious and comfortable semi-detached house is situated in a quiet residential neighbourhood within walking distance of Newport town centre. Situated at the top of a hill, the home boasts stunning views of the island and a well-kept private garden.  …see more

from £50 / night

£325 - £1930 / week

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from £50 / night

(31) Excellent 

23

Holiday home in Yarmouth

Isle of Wight / Yarmouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Wonderful holiday rental!” A lovely, spacious comfortable house with fantastic countryside views. We travelled with our young family and friends and all enjoyed staying at Three Gables. The kids loved the garden and played golf and boules (all provid  …see more

from £195 / night

£800 - £1775 / week

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from £195 / night

(15) Excellent 

20

Holiday home with golf nearby in Sandown

Isle of Wight / Sandown

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
2 bedroom new build sleeps up to 4 sandown off road parking 4 seater corner sofa downstairs toilet and upstairs bathroom isle of wight holiday let close to beach and train safe decking wifi enclosed garden summer sun  …see more

from £36 / night

£250 - £745 / week

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from £36 / night

24

Yarmouth holiday apartment rental

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
As part of the renovation to the main house (known as Waterfront house), Waterfront retreat is a lovingly designed cottage annexe with private entrance that has been created with style and relaxation in mind. If the flourish of designer driftwood ornaments and the pall  …see more

from £95 / night

£980 - £1050 / week

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from £95 / 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

(14) Excellent 

22

Ventnor holiday apartment rental

Ventnor / Ventnor Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Private garden
“Lovely Apartment” Stayed at Clarence House some years ago and now under new management the apartments have been very tastefully refurbished. We stayed in Osborne Apartment with one bedroom. Very comfortable and amazingly quiet considering all the othe  …see more

from £69 / night

£379 - £579 / week

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from £69 / 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

(3) Excellent 

15

Apartment rental in Shanklin

Shanklin / Old Village

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
“Superb” A very clean and comfortable apartment and beautiful gardens. Pam is a very nice and welcoming lady and nothing is too much trouble if you need anything. Will definitely be booking to go back next year at some point.  …see more

from £57 / night

£395 - £600 / week

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from £57 / 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

(5) Excellent 

12

Brading holiday cottage rental

Isle of Wight / Brading

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about pets
  • Private garden
A quirky little character cottage backing onto open fields & located in the ancient 'Kynges Towne' of Brading. The home offers all modern comforts & the well presented accommodation has a 'light & airy' feel. Outside, there are pretty gar  …see more

from £42 / night

£295 - £575 / week

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from £42 / night

(8) Excellent 

13

Holiday cottage in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“We had a lovely stay” Salt Air Cottage was lovely and Miriam had thought of everything to make our stay pleasant. The cottage was well kitted out and there were lots of little touches like phone charges, games to play, DVDs to watch and music to list  …see more

from £75 / night

£475 - £595 / week

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from £75 / night

(11) Very Good 

17

Holiday log cabin in Woodside Beach

Isle of Wight / Woodside Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Wonderful time,had by all” Great place to stay suitable for all ages, Recently been refurbished lovely. Friendly owners that make you very welcome. Very private area to enjoy the wildlife and relax during our stay. Very presentable with just a very sh  …see more

from £45 / night

£210 - £445 / week

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from £45 / night

(5) Excellent 

22

Barn rental in Ryde

Isle of Wight / Ryde

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“Fabulously spacious barn on working farm sleeping 12 with amazing views and” Really enjoyable stay at Kemphill Farm. Very spacious and incredibly well equipped with everything you could need. Plenty of space to sleep 12 of us young and old and each of  …see more

from £210 / night

£980 - £2400 / week

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from £210 / night

(5) Excellent 

16

Cowes holiday townhouse rental

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Beautiful West Cowes holiday flat” This flat is perfectly situated on the (pedestrian-only) high street. It is literally steps away from all the amenities and sights. The flat is very cozy, well equipped, and makes you feel like you are on holiday. Tw  …see more

from £150 / night

£650 - £950 / week

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from £150 / night

(8) Excellent 

10

Cottage rental in Whippingham

Isle of Wight / Whippingham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 10 km
  • Child friendly
  • Private garden
Self-catering countryside cottage, equipped to a high standard, with excellent views across fields. Located along a private lane, very secluded - the base for great holidays on the Isle of Wight - great for chilling out!! Ideal for couple & families seeking relaxati  …see more

from £49 / night

£340 - £625 / week

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from £49 / night

(7) Excellent 

20

Holiday apartment in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 1 km
  • Suitable for children age 5+
  • Car not necessary
“Great Location and Facilities” This modern and luxurious fully equipped apartment was ideal for our stay with our 87 year old Mother, 5 mins walk from centre of Cowes, with a balcony overlooking the Harbour and a designated on site parking space. Ca  …see more

from £100 / night

£370 - £2300 / week

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from £100 / night

(9) Very Good 

12

Freshwater holiday bungalow rental

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Great value for money!” We enjoyed our stay at this bungalow, good outlook, could see coast of dorset, easy access to coastal path. Would recommend highly, friendly owners and good value for money!  …see more

from £33 / night

£233 - £555 / week

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from £33 / night

13

Holiday townhouse in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
This centrally located cottage is great for small groups or sailing crews who want to be in the heart of the action Its located just behind The Coast Bar, It has recently been refurbished to a very high standard with lovely laminate flooring & new beds. Due to its  …see more

from £70 / night

£305 - £1200 / week

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from £70 / night

(2) Excellent 

20

Holiday apartment in Shanklin

Shanklin / Old Village

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Private garden
This beautifully presented and comfortable one bedroom first floor apartment is set in a peaceful and quiet location in the grounds of an Edwardian house in the coastal resort of Shanklin. It is attached to the owners house, but cleverly arranged for maximum privacy as  …see more

from £57 / night

£395 - £600 / week

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from £57 / night

(30) Excellent 

32

Holiday apartment in Shanklin

Shanklin / Luccombe Village

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night 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

(17) Excellent 

30

Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Great holiday cottage” The Dairy was very well presented, extremely clean and very comfortable for our family with two young children. It is very well equipped with everything you need for a self catering holiday. We especially loved the hot tub, e  …see more

from £125 / night

£370 - £795 / week

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from £125 / night

17

Holiday chalet rental

Isle of Wight / Sandown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Pet friendly and with free WiFi, 'Fossils Reach' is situated on a quiet part of the holiday park. It's not overlooked, and has a grassed area to the front with sea glimpses viewed through the trees. Local wildlife includes rabbits, foxes, pheasants and  …see more

from £35 / night

£240 - £450 / week

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from £35 / night

(7) Excellent 

18

Cowes holiday bungalow rental

Cowes / West Cowes

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Perfect in every way!” We knew as soon as we arrived we had made an excellent choice, the views from the bungalow were fabulous, the garden was amazing and we have never felt so comfortable and at home. The bungalow is very spacious, well set out, hug  …see more

from £90 / night

£450 - £3250 / week

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from £90 / night

(1) Excellent 

12

Bonchurch holiday cottage rental

Isle of Wight / Bonchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Private garden
Bonchurch has an air of peace and tranquility with its ancient churches, village pond and traditional cottages but it is also a working village. SPECIAL OFFERS AVAILABLE SEE HOME FROM HOME WEBSITE FOR DETAILS  …see more

from £87 / night

£350 - £600 / week

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from £87 / night

(10) Excellent 

14

Whitwell holiday cottage rental

Whitwell / Nettlecombe

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
These delightful cosy cottage is set within the attractive grounds at a retired Victorian Station and still has the atmosphere of a bygone era. There is a small Vineyard within the peaceful gardens its just a short walk to the village pub & rural life..<br />W  …see more

from £90 / night

£340 - £900 / week

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from £90 / night

(3) Average 

16

Wootton Bridge holiday cottage rental

Isle of Wight / Wootton Bridge

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Free broadband WiFi. Quiet location with the Island's renowned red squirrels frequent visitors. Wootton Bridge offers easy access to the Island's two main towns of Ryde and Newport, but also convenient for seaside locations and the more remote but beautiful We  …see more

from £125 / night

£875 / week

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from £125 / night

11

Newchurch holiday lodge rental

Sandown / Newchurch

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Winford Retreat is high standard, newly refurbished 4 bedroom 1 en suite chalet bungalow aimed at the 5 star market. Positioned in the prestigious area of Forest Road within a few minutes drive to lovely beaches, Towns and Villages.  …see more

from £214 / night

£1495 - £1545 / week

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from £214 / night

(1) Excellent 

12

Bembridge holiday home rental

Bembridge / Bembridge Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Ledge View is a beautiful newly-upgraded property sleeping up to 8 people just seconds from the sea in Bembridge, Isle of Wight. The house is in a fantastic location, due to its proximity to the stunning Forelands beach.  …see more

from £185 / night

£610 - £1540 / week

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from £185 / night

(8) Excellent 

14

Holiday apartment in Ventnor

Ventnor / Ventnor Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Brilliant apartment,brilliant location,brilliant views” Exactly what it says on'"the tin".Easy to book ,with confidence and all the support you would need-regular updates and support of "the lovely Lisa" on the island. Spacious and extremely well pre  …see more

from £145 / night

£750 - £1163 / week

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from £145 / night

(12) Very Good 

20

Chalet rental in Gurnard

Isle of Wight / Gurnard

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Superb and exquisite little gem, highly recommended” We stayed in Beachside for two magical days. It may have rained constantly but the cabin was so perfectly equipped we were happy to stay inside and cook in the very well equipped kitchen, read books  …see more

from £50 / night

£320 - £530 / week

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from £50 / night

(5) Excellent 

13

Gurnard holiday cottage rental

Isle of Wight / Gurnard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
All bookings come with 15% discount of Red Funnel ferries.free Courtesy bus for sailing events or those coming on foot. Parking for 3 cars.<br />Part of the Cowes Holiday Homes portfolio where quality matters  …see more

from £120 / night

£475 - £1300 / week

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from £120 / night

(2) Excellent 

11

Holiday apartment in Cowes

Isle of Wight / Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Superb modern two bedroom apartment on the second floor of Marinus which is adjacent to Shepards Wharf marina. Relax on the balcony and enjoy the ever-changing scene across the harbour and Eastern Solent. 5 minutes walk from the centre of Cowes.  …see more

from £125 / night

£400 - £2200 / week

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from £125 / night

(1) Excellent 

19

Holiday home in Shanklin

Isle of Wight / Shanklin

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Great location for exploring the Island, peacefull with lovely views, countryside from the rear and sea glimpses from the front of the house. Lovely walks into Shanklin Town via the railway track or through the farm, plus America Woods seconds away.<br />Balconies  …see more

from £350 / night

£1750 - £2500 / week

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from £350 / 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

(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

(1) Very Good 

11

Holiday townhouse in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
This cottage is ideal for those who don't have a car, Red Jet terminal & Bus Terminal & the heart of Cowes just a short walk away. Parking permits can be provided if required for the on street parking zone for those are bringing their car.<br />This  …see more

from £75 / night

£395 - £1600 / week

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from £75 / night

(4) Excellent 

16

Holiday townhouse rental

Isle of Wight / Cowes

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Car not necessary
“This place is so great we have been back again!” I have stayed here twice with extended family. The house is spacious and comfortable with great style. The property is located in a great spot with easy walking access to Cowes, a variety of shops, pubs  …see more

from £235 / night

£795 - £4600 / week

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from £235 / night

(1) Excellent 

17

Barn rental in Porchfield

Isle of Wight / Porchfield

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Pet friendly
Skilfully converted, this beautifully presented barn is perfect for either two groups or a larger family wishing to come away together. It offers beautiful accommodation in a quiet location surrounded by our own fields ,paddocks and woods.<br />Buzzard Barn prices  …see more

from £450 / night

£750 - £1800 / week

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from £450 / night

(6) Excellent 

19

Holiday home rental

Isle of Wight / Shanklin

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Enjoy time with family or friends in this newly renovated, spacious Edwardian villa, light and airy, with high ceilings and period features. It sleeps 9 in 4 bedrooms. Enjoy a game of pool or table tennis or play the piano in the games room. The house has BT Infinity  …see more

from £150 / night

£700 - £1880 / week

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from £150 / night

16

Cowes holiday guest house rental

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Suitable for children age 5+
  • Private garden
With its elevated position some of the rooms have views over Cowes & the Solent & it comes with its own parking space & good size garden.<br />This property is part of the Cowes Holiday Homes portfolio where good service comes as standard  …see more

from £250 / night

£1200 - £5200 / week

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from £250 / night