Cottages in Isle of Wight and Self catering accommodation – Holiday Lettings – Holiday Rentals Isle of Wight

from £35 / night

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Holiday home in Cowes

Isle of Wight / Cowes

4 10 Min stay varies

4 bedrooms
Sleeps 10
Min stay varies

Child friendly

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from £140 / night

£650 - £4,750 / week

from £140 / night

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Niton holiday chalet rental

Isle of Wight / Niton

1 2 3 nights min

1 bedroom
Sleeps 2
3 nights min

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from £72 / night

£236 - £337 / week

Responds fast!
avg. 1 hour 37 minutes

from £72 / night

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Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Child friendly
Private garden

“An idyllic setting” We stayed for a long weekend and were thoroughly delighted by every aspect of our stay. Our hosts were friendly and accommodating; the venue pristine and comfortable and we cannot wait to go back. Highly recommended!

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Certificate of Excellence

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from £110 / night

£450 - £850 / week

Responds fast!
avg. 1 hour 24 minutes

from £110 / night

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Ventnor Bay holiday apartment rental

Ventnor / Ventnor Bay

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Beach / lakeside relaxation
Child friendly

“Perfect in every way ...” We stayed for seven nights in The Carisbrooke Apartment. We were absolutely delighted with the accommodation .... newly refurbished and tastefully decorated throughout, Gillian and Robert really have thought of everything to make this a 5-star stay! The apartment is very spacious and airy - it is impressive but does not skimp on comfort. We certainly would not hesitate to recommend it to our family and friends and our first visit won't be our last ..... we would love to return. Osborne House is located opposite Ventnor Park with the town, beach and Ventnor's Botanical Gardens within comfortable walking distance.

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Certificate of Excellence

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from £95 / night

£495 - £995 / week

Responds fast!
avg. 1 hour 20 minutes

from £95 / night

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“fantastic stay”

Reviewed 21 Sep 2015

absolutely brilliant long weekend at Clarence House. Pure luxury and everything we could have wanted in a break away! Quality of facilities excellent. Have booked for next year already!… More

“Relaxed elegance in Ventnor”

Reviewed 11 Mar 2016

Our 2nd visit to this accommodation, this time staying in the 2 bedroomed Carisbrook apartment. Very comfortable, spacious, light and elegant accommodation with the added bonus of a wood burner and v… More

Holiday home in Sandown

Isle of Wight / Sandown

2 4 2 nights min

2 bedrooms
Sleeps 4
2 nights min

Beach / lakeside relaxation
Nearest beach 0.3 km
Suitable for children age 5+

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from £30 / night

£195 - £335 / week

Responds fast!
avg. 3 hours 55 minutes

from £30 / night

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Holiday bungalow in Brading

Isle of Wight / Brading

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Child friendly
Car not necessary
Private garden

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from £450 / night

£400 - £525 / week

from £450 / night

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Gurnard holiday home rental

Isle of Wight / Gurnard

3 7 Min stay varies

3 bedrooms
Sleeps 7
Min stay varies

Nearest beach 0 km
Child friendly
Pet friendly

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from £145 / night

£595 - £2,170 / week

Responds fast!
avg. 1 hour 37 minutes

from £145 / night

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Apartment rental in Shanklin

Isle of Wight / Shanklin

3 6 Min stay varies

3 bedrooms
Sleeps 6
Min stay varies

Nearest beach 0.5 km
Child friendly
Car not necessary

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from £120 / night

£600 - £1,650 / week

Responds fast!
avg. 2 hours 48 minutes

from £120 / night

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Holiday apartment in Ryde

Isle of Wight / Ryde

1 2 2 nights min

1 bedroom
Sleeps 2
2 nights min

Beach / lakeside relaxation
Nearest beach 8 km

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from £60 / night

£400 - £430 / week

from £60 / night

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Holiday home in Brighstone

Isle of Wight / Brighstone

6 12 Min stay varies

6 bedrooms
Sleeps 12
Min stay varies

Beach / lakeside relaxation
Child friendly
Pet friendly

“A fantastic house, great location, with style as well as homely touches” We were a large group with ages ranging from 9 to early 80's plus a dog. The house had ample parking, comfy beds, a well equipped kitchen,cotton bed linen, fluffy towels and the two sitting rooms worked well allowing the adults and children to have time out from each other. Baked potatoes cooked in the Aga were so good we did the same again the next day. We stayed for 5 days and found more than enough to do. We would love to return one day.

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from £359 / night

£2,667 - £3,700 / week

Responds fast!
avg. 1 hour 26 minutes

from £359 / night

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“Wonderful house for a large gathering on the Isle of Wight”

Reviewed 13 Jan 2013

We stayed at the Mill House with two other families for a week over New year. The house is very warm and friendly and extremely well equipped. The three main double bedrooms are equally delightful wh… More

“Beautiful family home we go every year.”

Reviewed 18 Apr 2012

We first found The Millhouse four years ago and have been every year since. We go with my parents, siblings and their famiies - its a great house for family groups and works really well for us. The h… More

“Fantastic family holiday”

Reviewed 10 Apr 2012

Thank you for a wonderful holiday in the Isle of Wight. The house is extremely well equipped to a high standard with everything you need for a holiday - with a lot of thought to those with young child… More

Ventnor holiday apartment rental

Isle of Wight / Ventnor

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Nearest beach 0.1 km
Car not necessary
Private garden

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from £90 / night

£850 - £880 / week

Responds fast!
avg. 1 hour 14 minutes

from £90 / night

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Holiday cottage in Ventnor

Isle of Wight / Ventnor

4 7 Min stay varies

4 bedrooms
Sleeps 7
Min stay varies

Beach / lakeside relaxation
Nearest beach 0.4 km
Child friendly

“Beautiful Cottage” We had a fabulous stay here at Ventnor . A beautiful cottage equipped with everything we needed for a lovely week in our favourite place . A great location so close to the town which has plenty of great shops , tea shops and even the best ice cream parlor and only a short walk to the beach . We also loved the garden and barbecue . Thank you Alun and Sheelagh for a lovely stay .

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from £95 / night

£525 - £1,024 / week

Responds fast!
avg. 2 hours 18 minutes

from £95 / night

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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

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from £60 / night

£275 - £480 / week

from £60 / night

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Holiday apartment in Ventnor

Isle of Wight / Ventnor

3 6 3 nights min

3 bedrooms
Sleeps 6
3 nights min

Nearest beach 0.1 km
Child friendly
Car not necessary

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from £145 / night

£750 - £1,163 / week

Responds fast!
avg. 2 hours 49 minutes

from £145 / night

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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

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from £250 / night

£1,400 - £1,975 / week

from £250 / night

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Gurnard holiday lodge rental

Isle of Wight / Gurnard

3 6 Min stay varies

3 bedrooms
Sleeps 6
Min stay varies

Swimming pool
Child friendly

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from £112 / night

£449 - £1,195 / week

Responds fast!
avg. 1 hour 37 minutes

from £112 / night

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Holiday apartment in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Child friendly

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from £90 / night

£370 - £645 / week

Responds fast!
avg. 2 hours 18 minutes

from £90 / night

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Holiday home in Bonchurch

Ventnor / Bonchurch

4 8 3 nights min

4 bedrooms
Sleeps 8
3 nights min

Nearest beach 1 km
Child friendly
Ask about pets

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from £225 / night

£1,575 / week

from £225 / night

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Shanklin holiday home rental

Isle of Wight / Shanklin

4 8 7 nights min

4 bedrooms
Sleeps 8
7 nights min

Beach / lakeside relaxation
Child friendly
Private garden

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from £100 / night

£695 - £1,595 / week

from £100 / night

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Holiday cottage in Yarmouth

Isle of Wight / Yarmouth

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Child friendly
Private garden

“Amazing, comfortable cottage in beautiful location” From the lovely welcome to "The Old Barn" right through our whole weeks stay we had nothing bad to say. The cottage was amazing, beautifully finished and spotless within. The hot tub was a lovely added extra which my teenage daughter adored spending time in day & night. Everything you could possibly need on a week away was in the property, even DVDs and a few games to play which was a nice touch. I even managed to read a book from cover to cover from the cottages bookshelves, haven't done that in years! Great location with some nice towns and beaches within a short drive. If you want a nice family break in a superb cottage then this is the one for you, would highy recommend.

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from £150 / night

£700 - £1,550 / week

Responds fast!
avg. 1 hour 24 minutes

from £150 / night

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“Exceeded all our expectations”

Reviewed 6 Jun 2013

A lovely property - stylish, yet comfortable and well very equipped. The garden & courtyard is perfect for lazy afternoon/evening BBQs and lounging in the hot tub! Nick and Kristina were the perfect … More

“What a find!”

Reviewed 9 May 2013

Absolutely a stunning find, this recently converted Barn really had everything we could need including a Jacuzzi in the garden! On arrival we found a hamper to cater for our initial needs including a… More

Holiday home with golf nearby in Sandown

Isle of Wight / Sandown

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Beach / lakeside relaxation
Nearest beach 0.3 km
Child friendly

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from £49 / night

£295 - £745 / week

Responds fast!
avg. 12 minutes

from £49 / night

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Yarmouth holiday home let

Isle of Wight / Yarmouth

3 8 Min stay varies

3 bedrooms
Sleeps 8
Min stay varies

Beach / lakeside relaxation
Child friendly
Ask about pets

“Home from Home” Very nice, clean and spacious cottage. Made feel really welcome with great Hamper, extra bonus was the christmas tree. We stayed in the Cottage over the christmas holiday and it was wonderful. The Storms did not bother us as we were very cosy inside the cottage. It was like home from home, all the kitchen appliances and utensils were supplied, nothing at all missing. The location is ideal as it is only a few minutes away from the ferry. Yarmouth is a really quaint little town, we loved it.

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from £147 / night

£725 - £1,250 / week

from £147 / night

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Holiday home in Ventnor

Isle of Wight / Ventnor

3 6 Min stay varies

3 bedrooms
Sleeps 6
Min stay varies

Nearest beach 0.2 km
Child friendly
Car not necessary

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from £80 / night

£700 / week

from £80 / night

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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

“Fantastic place, great location, good value” Myself and twelve other guys stayed at Little Orchard as part of a stag weekend. There were no problems booking - the owner was very understanding, which was great as we're a group in our mid-thirties, but I was worried that the stigma of the typical stag-party-wrecking-the-place might be attached to us! The house is really fantastic - large, well-kept and with plenty of facilities for a large group: massive fridge-freezer, two large ovens, three bathrooms. It's in a great location for anyone planning to visit Cowes; just a few minutes walk to the Parade, a few more minutes to the pubs and shops beyond. From the large garden you could even see the beautiful sea, with yachts floating by. There's a barbecue too, a well-stocked larder, and comfy beds with all towels and linen were provided. I'd have no hesitation in returning to Little Orchard again, perhaps with extended family for a few day enjoying the Isle of Wight.

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from £395 / night

£2,000 - £3,250 / week

from £395 / night

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Home rental in Nettlestone with golf nearby

Isle of Wight / Nettlestone

5 10 Min stay varies

5 bedrooms
Sleeps 10
Min stay varies

Beach / lakeside relaxation
Nearest beach 1 km
Child friendly

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from £250 / night

£1,450 - £2,045 / week

Responds fast!
avg. 40 minutes

from £250 / night

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Sandown holiday chalet rental

Isle of Wight / Sandown

2 4 3 nights min

2 bedrooms
Sleeps 4
3 nights min

Beach / lakeside relaxation
Child friendly

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from £39 / night

£225 - £400 / week

from £39 / night

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Bungalow rental in Yarmouth

Isle of Wight / Yarmouth

4 9 Min stay varies

4 bedrooms
Sleeps 9
Min stay varies

Beach / lakeside relaxation
Nearest beach 5 km
Child friendly

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from £120 / night

£500 - £1,800 / week

from £120 / night

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Freshwater holiday tented camp rental

Isle of Wight / Freshwater

3 8 Min stay varies

3 bedrooms
Sleeps 8
Min stay varies

Nearest beach 4 km
Child friendly
Car not necessary

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from £204 / night

£945 - £1,380 / week

from £204 / night

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Holiday apartment in Shanklin

Isle of Wight / Shanklin

2 6 Min stay varies

2 bedrooms
Sleeps 6
Min stay varies

Swimming pool
Child friendly
Private garden

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from £74 / night

£665 - £1,208 / week

Responds fast!
avg. 2 hours 46 minutes

from £74 / night

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Holiday home in Cowes

Cowes / West Cowes

4 8 Min stay varies

4 bedrooms
Sleeps 8
Min stay varies

Beach / lakeside relaxation
Nearest beach 2 km
Child friendly

“Lovely stay at the new Crew's Nest” We had previously stayed at the original Crew's Nest on St Mary's Road so we knew that we were going to be in for a lovely stay. The property has been done up beautifully and has all the little touches that make a stay special - even to an Outback gas BBQ in the garden for residents to use! You couldn't be closer to the town and all the facilities, and is also a great base from which to explore the rest of the island, which is what we did on this particular visit. In Cowes, can highly recommend Mojacs for something to eat, and Tiffins do a great bacon baguette for a bit of breakfast on the run! Will be coming back (again!)

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from £175 / night

£750 - £3,070 / week

from £175 / night

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Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 2 3 nights min

1 bedroom
Sleeps 2
3 nights min

Car not necessary

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from £60 / night

£420 / week

from £60 / night

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Villa letting in Cowes

Cowes / West Cowes

5 11 Min stay varies

5 bedrooms
Sleeps 11
Min stay varies

Child friendly
Ask about pets
Private garden

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from £170 / night

£800 - £5,200 / week

from £170 / night

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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+

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from £165 / night

£750 - £1,200 / week

from £165 / night

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Holiday apartment in Cowes

Cowes / West Cowes

1 4 Min stay varies

1 bedroom
Sleeps 4
Min stay varies

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from £70 / night

£340 - £950 / week

from £70 / night

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Shanklin holiday home rental

Isle of Wight / Shanklin

1 2 1 night min

1 bedroom
Sleeps 2
1 night min

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from £118 / night

£826 / week

from £118 / night

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B&b rental in Shanklin

Isle of Wight / Shanklin

1 2 2 nights min

1 bedroom
Sleeps 2
2 nights min

Child friendly

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from £73 / night

£511 / week

from £73 / night

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Freshwater holiday apartment rental

Freshwater / Freshwater Bay

2 4 2 nights min

2 bedrooms
Sleeps 4
2 nights min

Beach / lakeside relaxation
Child friendly

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from £75 / night

£325 - £895 / week

Responds fast!
avg. 1 hour 5 minutes

from £75 / night

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Holiday cottage in Brading

Isle of Wight / Brading

2 4 Min stay varies

2 bedrooms
Sleeps 4
Min stay varies

Beach / lakeside relaxation
Nearest beach 2 km
Child friendly

“Marmalde Cottage, the perfect Isle of Wight holiday home” The pictures of Marmalade Cottage don't do it justice, we arrived on a somewhat rainy Saturday and were greeted by Colin and Julie, how made us feel instantly welcome and were on hand to provide any help for our stay. When we entered the lovely spacious annex cottage, we found the house to be really well laid out with plenty of room for my daughter to play, they house was well equipped with lovely gardens and in a perfect location for the beaches, shops and things to do.

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Certificate of Excellence

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from £95 / night

£450 - £850 / week

Responds fast!
avg. 1 hour 19 minutes

from £95 / night

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Home rental 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

“Beautiful house with lovely garden” Regatta Cottage is a lovely rental, equipped to a very high standard and clearly recently refurbished. The welcome basket was a lovely surprise and made our lives much easier particularly as we were only there for a weekend. Key pick up and return is at a local pub (in West Cowes centre near the hi speed ferry) and was nice and easy. Is about 5-10mins walk from the property. There are several keys which is useful for large groups. The garden looked lovely but we didn't really get a chance to use it, mores the pity.

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from £200 / night

£750 - £2,600 / week

from £200 / night

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“Spotless and spacious property in a perfect location.”

Reviewed 18 Apr 2012

We had a wonderful holiday at Regatta Cottage. The property owner was extremely helpful throughout the booking process and during our stay. The house is beautifully decorated, very well equipped and s… More

Thank you for your lovely review. We are so pleased that you enjoyed your stay at Regatta Cottage.

“Perfectly located and spotlessly clean”

Reviewed 10 Apr 2012

Super location for strolling into the centre of Cowes. Spotlessly clean. Lovely welcome pack.… More

Many thanks for your review of Regatta Cottage, we always appreciate it when guests spare a few moments to leave some feedback. I'll pass on your comments about how spotlessly clean the house was to our changeover team.

“family Holiday”

Reviewed 29 Aug 2016

We returned to the Isle of Wight after many years and have had the most relaxing time the accommodation was excellent and well stocked we found parking a daily challenge but so did everyone else it di… More

Thank you for taking the time to leave a review. I am delighted that you enjoyed staying at Regatta Cottage and I hope to welcome you back at some time in the future. Amanda