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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Winchester chalets

Outdoor dining
Creek View, Isle of Wight

Chalet in Wootton Bridge

Creek View, Isle of Wight
10.0 out of 10, Exceptional, (2)
"A truly amazing stay at a wonderful location. A superb home to base an island adventure! "
United States
Benjamin G.
The price is AED 25,327
AED 28,181 total
includes taxes & fees
2 Jan - 3 January 2026
Creek View, Isle of Wight
Exterior
York Street

Chalet in Cowes

York Street
10.0 out of 10, Exceptional, (8)
"It was absolutely perfect ! The house was so well looked after ."
United States
Anonymous traveler
The price is AED 4,274
AED 4,973 total
includes taxes & fees
17 Jan - 18 January 2026
York Street
Outdoor spa tub
Dassia

Chalet in Porchfield

Dassia
9.6 out of 10, Exceptional, (4)
"We stayed here over Christmas and it was perfect. Our dog loved the enclosed garden. The kitchen has everything to cook a festive dinner in. We had the log burner on for the day which was great. Would definitely stay again."
United States
Emma
The price is AED 3,356
AED 3,939 total
includes taxes & fees
2 Jan - 3 January 2026
Dassia
Terrace/patio
Princes Esplanade

Chalet in Gurnard

Princes Esplanade
10.0 out of 10, Exceptional, (3)
"We loved the beautiful location"
United States
Susan
The price is AED 3,198
AED 3,888 total
includes taxes & fees
18 Jan - 19 January 2026
Princes Esplanade
Exterior
No 1 Ashey

Chalet in Ryde

No 1 Ashey
9.4 out of 10, Exceptional, (18)
"We stayed here for three nights and loved it! The weather was amazing so we made the most out of the pool. The house is very clean and spacious."
United States
Anonymous traveler
The price is AED 5,065
AED 5,918 total
includes taxes & fees
3 Jan - 4 January 2026
No 1 Ashey
Exterior
6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms

Chalet in Emsworth

6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms
9.6 out of 10, Exceptional, (81)
"Can't say better than a return visit. Very comfortable base, with a beautiful balcony with views over the water and marsh. Lovely place to relax in the evening after a day exploring this beautiful part of the country."
United States
Brodie S.
The price is AED 3,865
AED 3,865 total
includes taxes & fees
18 Jan - 19 January 2026
6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms
Exterior
St Georges Villa

Chalet in Ryde

St Georges Villa
The price is AED 3,229
AED 3,775 total
includes taxes & fees
4 Jan - 5 January 2026
St Georges Villa
Outdoor dining
Penderic, Isle of Wight

Chalet in Cowes

Penderic, Isle of Wight
The price is AED 3,324
AED 3,978 total
includes taxes & fees
2 Jan - 3 January 2026
Penderic, Isle of Wight
Exterior
George Street House

Chalet in Ryde

George Street House
6.0 out of 10, (1)
"The property is spacious and is well placed for access to the town.However we found the lack of parking to be an added anxiety at the end of the day. Although told we could park in Co-op the signs said it closed with the shop at 8pm so we didn't risk it.Also the windows were extremely hard to open and close and didn't provide any noise reduction from the the very busy road. Buses ran until midnight and glazier and Co-op were both un/loading by 7am.We also had a ring doorbell go at 8.30 on 2...
United Kingdom
Karen R.
The price is AED 3,672
AED 4,262 total
includes taxes & fees
30 Jan - 31 January 2026
George Street House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

The Winchester Hotel & Spa

The Winchester Hotel & Spa

10/10 Excellent
"Brilliant spa and nice clean room "
Joe 2-night trip
Posted 1 day ago
The Winchester Hotel & Spa