Cycling holiday villas and apartments Isle of Wight

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  • Bembridge (21)
  • Bemridge Harbour (1)
  • Bonchurch (7)
  • Brading (4)
  • Brighstone (5)
  • Brook (2)
  • Calbourne (4)
  • Cowes (48)
  • East Cowes (4)
  • Freshwater (24)
  • Godshill (5)
  • Gurnard (12)
  • Knighton, Isle of Wight (1)
  • Nettlestone (1)
  • Newport (7)
  • Newtown (1)
  • Niton (6)
  • Porchfield (3)
  • Rookley (1)
  • Ryde (19)
  • Sandown (41)
  • Seaview (10)
  • Shanklin (35)
  • Shorwell (5)
  • St Helens (3)
  • Totland Bay (5)
  • Ventnor (54)
  • Wellow (2)
  • Whippingham (6)
  • Whitwell (5)
  • Wootton Bridge (9)
  • Wroxall (6)
  • Yarmouth (18)

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375 Holiday homes

Filters applied: Cycling holidays (375)

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

(2) Very Good 

21

Westridge House - Ryde house sleeps 10

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. Despite being built over 100 years ago, the house is furnished to an extremely high  …see more

from £700 / night

£2250 - £4495 / week

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from £700 / night

(14) Very Good 

23

Hurst View - Norton - Isle of Wight townhouse sleeps 6

Yarmouth / Norton, Isle of Wight

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Awarded a 4 Star accreditation from VisitEngland Hurst View offers high quality Self Catering holiday accomodation for up to 6 guests in this end of terrace townhouse. Hurst View offers high quality holiday accommodation in the attractive and popular holiday resort of N  …see more

from £54 / night

£378 - £970 / week

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from £54 / night

(14) Very Good 

24

Cedar Croft - Cowes log cabin sleeps 5

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Take a peaceful break away from the crowds in our quirky little cabin. Get up have a stroll along the beach, on our private bay, then sit outside and have breakfast while looking at the beautiful view and watching the boats sail by, you may want to spend time with your  …see more

from £57 / night

£400 - £670 / week

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from £57 / night

(14) Excellent 

13

Springfield cottage - Newchurch bungalow sleeps 2

Sandown / Newchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Private garden
One bedroom bungalow in the garden near to the owners property with its own private patio. Situated in the peaceful village of Newchurch popular with walkers nature lovers and cyclists. The comfortable accomodation is all on ground level with no steps and easily acce  …see more

from £85 / night

£340 - £600 / week

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from £85 / night

(19) Very Good 

24

Rush House - Old Village house sleeps 18

Shanklin / Old Village

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Recently graded by a national holiday home company as a 5 star property. Luxury 8 bedroom holiday home, in sunny shanklin. modern and newly built large detached house on the outskirts of the beach and old village on the south of the isle of wight. Suitable for groups or  …see more

from £775 / night

£2200 - £3800 / week

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from £775 / night

(1) Excellent 

14

Alban House, Cowes. overlooking the Marina - West Cowes house sleeps 12

Cowes / West Cowes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
A superb house in the Cowes recently refurbished to a high standard overlooking the marina with its own pontoon. The house has central heating and double glazing. This modern town house split over 4 levels has a large fully fitted kitchen including a dishwasher, fridge  …see more

from £500 / night

£2000 - £3500 / week

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from £500 / night

(12) Very Good 

9

BOUTIQUE BEACH HOUSE WITH SEA VIEWS - Gurnard house sleeps 4

Isle of Wight / Gurnard

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
A boutique beach house featured in COAST magazine (see photos) offering simple, comfortable and chic living, set over 2 floors with a multitude of sunny outside spaces and decks with sea views, set in the sought after area of old Gurnard just yards from the sandy beach.  …see more

from £55 / night

£385 - £1575 / week

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from £55 / night

(10) Excellent 

19

The Old Brewhouse - Calbourne cottage sleeps 5

Isle of Wight / Calbourne

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Set in a rural location in the grounds of an 18th century farmhouse with 1.5 acres of land. the Old Brewhouse is a delightful 2 bedroomed converted brewhouse which won a design award following completion. The accommodation comprises a ground floor double bedroom with a  …see more

from £100 / night

£400 - £800 / week

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from £100 / night

(23) Very Good 

22

Victorian Cottage in Cowes - West Cowes cottage sleeps 4

Cowes / West Cowes

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
This is a Victorian Fishing Cottage in West Cowes on the Isle of Wight. The cottage is on a quiet street, unfortunately there isn't any parking out side, but there is plenty around in the other streets. To walk into the town would take you around five minutes  …see more

from £95 / night

£600 / week

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from £95 / night

(9) Excellent 

24

Clevelands Country House - Wroxall manor house sleeps 12

Isle of Wight / Wroxall

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Cleveland's Country House offers some of the best quality self-catering accommodation on the island. All accommodation is tastefully decorated throughout to a high standard and extremely well equipped to create a cosy, informal and relaxed atmosphere, a true home from h  …see more

from £350 / night

£1875 - £2800 / week

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from £350 / night

(25) Excellent 

15

The Lodge ( Strictly Over 25s only) - Ryde lodge sleeps 2

Isle of Wight / Ryde

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
This welcoming lodge really is a home from home all recently refurbished to a very high luxury standard. (Over 25 only).The accommodation sleeps 2 and the lodge is situated in a secluded area surrounded by woodland, yet not far from the beautiful sandy beaches and ch  …see more

from £60 / night

£350 - £850 / week

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from £60 / night

(6) Excellent 

10

Bucks Farm (Bike Shed) - Billingham barn sleeps 2

Shorwell / Billingham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
Very recently converted barn into three superb self contained units, each sleeping two people . Bucks Farm is situated near the glorious south coast of the Island in rolling countryside with stunning panoramic views all around. It is ideal for walkers, cyclists,surfers  …see more

from £70 / night

£450 - £550 / week

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from £70 / night

(3) Excellent 

18

Pond Cottage - Newport house sleeps 4

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
Pond Cottage is a farm building in the manor of Horringford, once the home of Oliver Cromwell's grandson. Converted in 2009, it is fitted to a very high standard with modern comfortable furnishings and all mod cons including TVs, washing machine, dishwasher, fridge  …see more

from £80 / night

£245 - £350 / week

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from £80 / night

16

3, HARBOUR STRAND - Bembridge Harbour townhouse sleeps 6

Bembridge / Bembridge Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
FOUR STAR, VISIT BRITAIN GRADE, SELF CATERING YACHTSMAN's Residence. 50 metres Yacht Club, Marina & Sandy Beach, Spacious & modernised Family home, Sleeps Six in comfort. Redecorated 2011.WELL APPOINTED, 3 BEDROOM 3 Floor HARBOUR HOME. Ground Floo  …see more

from £99 / night

£440 - £695 / week

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from £99 / night

(1) Very Good 

12

Ocean View holiday bungalow - Freshwater bungalow sleeps 4

Isle of Wight / Freshwater

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Child friendly
Situated in West Wight, one of the prettiest and most unspoilt parts of the island, our Ocean View holiday bungalow is located on the coastal path above the sandy beach of Colwell Bay. Offering spectacular views of the sea and the famous Needles Lighthouse, it is only a  …see more

from £30 / night

£190 - £375 / week

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from £30 / night

(11) Excellent 

7

Squirrel Nutkins cabin - Whippingham log cabin sleeps 2

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.•Pubs and res  …see more

from £60 / night

£350 - £450 / week

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from £60 / night

(20) Excellent 

19

CHARMING COTTAGE IN COWES - Cowes cottage sleeps 4

Isle of Wight / Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
A recently renovated (2015) town cottage, comfortably sleeping 4, consisting of one double bedroom (king size bed) and a large bathroom with a walk in shower on the first floor, and a twin singles bedded room on the 2nd floor. On the ground floor a separate sitting room  …see more

from £55 / night

£1575 / week

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from £55 / night

(6) Excellent 

26

2 The Granary, Brighstone - Brighstone cottage sleeps 4

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
Charming Grade II listed character cottage, quietly situated on the edge of the pretty village of Brighstone, 1/2 mile from the sea. 2 The Granary originally formed part of Brighstone Mill and dates back to 1700. Converted in 1990, the living room is on the first floor  …see more

from £99 / night

£375 - £785 / week

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from £99 / night

(1) Excellent 

12

Ledge View - Bembridge Village house sleeps 6

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 stunning home yards from the popular Forelands Beach in Bembridge, sleeping up to 8 people. The house has been recently upgraded and furnished to a very high standard throughout and also has plenty of parking space. The traditional and friendly Crab and  …see more

from £100 / night

£595 - £1295 / week

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from £100 / night

(8) Excellent 

14

Grange Farm Static Caravans - Brighstone Bay caravan/mobile home sleeps 6

Brighstone / Brighstone Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
The Static Caravan is set on a plateau where the Brighstone Life Boat Station was situated many years ago. It enjoys great views of the Sea and Chine, with very easy access to our sandy beach (see Brighstone Bay).Grange Farm, Brighstone Bay, is situated on the South We  …see more

from £59 / night

£355 - £575 / week

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from £59 / night

(16) Excellent 

30

1 The Dairy - Yarmouth cottage sleeps 4

Isle of Wight / Yarmouth

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
This converted Dairy Cottage is the ultimate in relaxing, set in a quiet farm location in the beautiful West Wight countryside.The cottage has its own private garden and terrace area with secure parking, and benefits from a hot tub which is shared between 3 properties o  …see more

from £110 / night

£370 - £795 / week

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from £110 / night

(3) Excellent 

15

Bella Vista - Ventnor apartment sleeps 2

Isle of Wight / Ventnor

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Car not necessary
The bedroom has a king size bed. The fitted kitchen is well appointed with all the facilities and appliances you could possibly need. The breakfast bar overlooks the lounge through a huge open window space creating a wonderful light and bright feel to the main living a  …see more

from £54 / night

£375 - £595 / week

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from £54 / night

(16) Very Good 

15

Fossils Reach 106 Sandown Bay Holday Centre - Yaverland chalet sleeps 6

Sandown / Yaverland

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Fossils Reach is a brick built, double glazed, modern, contemporary furnished holiday Chalet .The open plan lounge/kitchen/diner is furnished with a two seater sofa, a two seater sofa bed, a dining table with four chairs and a flat screen TV with Freeview, DVD and CD.  …see more

from £35 / night

£180 - £400 / week

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from £35 / night

(3) Excellent 

16

Hope Cottage - Totland Bay cottage sleeps 6

Totland Bay / Totland Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Hope cottage is situated in a quiet country lane in Totland, near the western tip of the Isle of Wight. The sandy beaches of Totland and Colwell Bay are within walking distance (new beach bar providing healthy options). The Idyllic Freshwater Bay is a longer walk or sho  …see more

from £75 / night

£350 - £628 / week

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from £75 / night

(7) Very Good 

15

Beach House, First Floor - Totland Bay apartment sleeps 6

Totland Bay / Totland Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
This luxurious spacious apartment is literally a stone's throw from the sea. It is almost like being on board a luxury cruise liner with stunning views of the unspoilt pretty Totland Bay. There are 2 bathrooms, large lounge/ dining room, king size, double and a t  …see more

from £135 / night

£500 - £1250 / week

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from £135 / night

11

Private Static Caravan Whitecliff Bay Holiday Park - Bembridge caravan/mobile home sleeps 8

Isle of Wight / Bembridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Available for holiday hire, is our large 4 bedroom static caravan set in the stunning surroundings of Whitecliff Bay Holiday Park in Bembridge. The caravan is very spacious, with 4 separate bedrooms, an open plan living and dining area, shower room with toilet and also  …see more

from £50 / night

£500 - £750 / week

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from £50 / night

(11) Excellent 

12

The Yachtsman - West Cowes townhouse sleeps 10

Cowes / West Cowes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary
The Yachtsman offers high quality self-catering accommodation in the heart of nautical Cowes, close to all facilities in this vibrant seaside town. The property is ideal for sailors, walkers and cyclists, being ideally situated close to the marinas and cycle paths. D  …see more

from £200 / night

£795 - £3250 / week

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from £200 / night

(6) Excellent 

24

St Michael's Cliff - Bonchurch house sleeps 10

Isle of Wight / Bonchurch

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
'Boutique hotel meets Country House' is how one reviewer described our lovely home in Bonchurch, a beautiful village on the south of the island. The village was recently voted No 5 in The Times list of ' 50 Best Places to Live By the Sea'. They said: "Why is it so great  …see more

from £372 / night

£2600 - £2700 / week

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from £372 / night

(27) Excellent 

22

Stable Cottage - Freshwater Bay barn sleeps 6

Freshwater / Freshwater Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
We can book you discount Redfunnel ferry tickets. Stable Cottage, set in the grounds of Afton Farmhouse, is in an 'Area of Outstanding Natural Beauty' on the west of the Isle of Wight. Awarded a 4 star rating by visit England. Afton, on the outskirts of Freshwater, i  …see more

from £55 / night

£360 - £1080 / week

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from £55 / night

(15) Very Good 

21

Springside - Whippingham cottage sleeps 5

Isle of Wight / Whippingham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
SPRINGSIDE self catering holiday cottage, Whippingham, Isle of Wight is a quality holiday cottage set in beautiful gardens with a lovely heated swimming pool shared with owners only. The pool is 4'6" shallow end and 6'6" deep end. Built for Queen Victoria and Prince Al  …see more

from £115 / night

£695 - £1500 / week

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from £115 / night

(3) Very Good 

12

Seabreeze - Freshwater bungalow sleeps 4

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
The property was built in 2007 and the accommodation is built and furnished to a high standard. We have lots of guests who have been booking their holidays in Seabreeze for many years. Seabreeze is located in a quiet and peaceful location, just the thing to unwind fr  …see more

from £30 / night

£210 - £544 / week

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from £30 / night

(4) Excellent 

18

The Watch House - East Cowes house sleeps 6

Isle of Wight / East Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The Watch House is a light, spacious & comfortable house; with high ceilings in the old section, that was renovated the house in 2012. An ideal location for sailors, fishermen and anyone that just want to watch the world go by. On a warm evening you can relax peacefull  …see more

from £135 / night

£400 - £750 / week

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from £135 / night

(1) Very Good 

10

The Furlongs; a bungalow with secluded garden. - Brading bungalow sleeps 4

Isle of Wight / Brading

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
The Furlongs is a two-bedroom bungalow that has been upgraded and is ideally located for parties wishing to explore all the Island has to offer. The Furlongs is a short 10 minute drive from the beautiful sandy beaches of Sandown and Yaverland. Attractions such as the Is  …see more

from £47 / night

£330 - £550 / week

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from £47 / night

(1) Excellent 

24

Chain Ferry House - West Cowes house sleeps 10

Cowes / West Cowes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
Amazing property for up to10 people 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. A Quay Management p  …see more

from £200 / night

£1400 - £5500 / week

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from £200 / night

(11) Excellent 

24

Rose Cottage - Roud cottage sleeps 6

Godshill / Roud

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Swimming pool
Rose Cottage. Is a traditional thatched cottage in the heart of the tiny hamlet of Roud on the Isle of Wight. The Cottage stands in almost 3 acres of garden where there is a unheated swimming pool, a large pond with elevated summer house and a separate trampoline area f  …see more

from £79 / night

£550 - £995 / week

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from £79 / night

(16) Excellent 

22

West View- Visit England Gold Award - Ryde cottage sleeps 4

Isle of Wight / Ryde

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
Built in 1850 West View is a mews cottage which has been moderrnised and refurbished to a high standard making it an ideal base for an Isle of Wight holiday. It is close to the beaches, opposite the tennis club, central to all the shops and attractions of Ryde, 10 minut  …see more

from £58 / night

£300 - £800 / week

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from £58 / night

(7) Very Good 

22

Little Orchard - West Cowes house sleeps 14

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
Little Orchard is a large six bedroom Art Deco style detached house situated in beautiful landscaped gardens. It benefits from a large through lounge/dining room and an extremely well equipped kitchen with both a four oven Aga and large range cooker as well as an Ameri  …see more

from £295 / night

£2500 - £3500 / week

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from £295 / night

(15) Excellent 

25

Little Mount - Totland Bay cottage sleeps 5

Totland Bay / Totland Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
This lovely spacious and peaceful house, which is graded four stars by Visit England, is on the edge of an Area of Outstanding Natural Beauty and the National Trust coastal path adjoins the garden, running down to the beach in one direction and up to Headen Warren with  …see more

from £99 / night

£695 - £985 / week

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from £99 / night

(4) Very Good 

22

Pink Beach Cottage - St Helens cottage sleeps 4

Isle of Wight / St Helens

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 2 km
  • Child friendly
  • Private garden
Pink Beach Cottage is an older style detached home situated in a quiet little road just of the village green. The accommodation is nicely presented offering two bedrooms being a double & a twin room. Downstairs there is characterful lounge with its feature fireplace,  …see more

from £83 / night

£295 - £450 / week

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from £83 / night

(9) Very Good 

16

SeaShells - Freshwater chalet sleeps 5

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
An open-plan lounge with dining area and kitchen, 2 bedrooms and a bathroom. Located on a 40 acre communal site. Large grassed area to the front of the property with a paved patio area which includes table and chairs allowing you to while away the hours watching the boa  …see more

from £33 / night

£199 - £495 / week

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from £33 / night

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