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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Winchester chalets

Exterior
York Street

York Street

York Street
Cowes
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 4,277
AED 4,975 total
includes taxes & fees
21 Dec - 22 Dec
York Street
Terrace/patio
Creek View, Isle of Wight

Creek View, Isle of Wight

Creek View, Isle of Wight
Wootton Bridge
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 6,919
AED 7,931 total
includes taxes & fees
15 Jan - 16 January 2026
Creek View, Isle of Wight
Outdoor dining
The Lymington Hub Slps 13 hot tub/chef/spa

The Lymington Hub Slps 13 hot tub/chef/spa

The Lymington Hub Slps 13 hot tub/chef/spa
Lymington
10.0 out of 10, Exceptional, (2)
"My wife and I had a wonderful weekend at Brook House with our family. Brook House was the perfect place to celebrate our Diamond Wedding anniversary. We had a great time. "
United States
KENNETH B.
The price is AED 4,914
AED 6,703 total
includes taxes & fees
1 Jan - 2 January 2026
The Lymington Hub Slps 13 hot tub/chef/spa
Exterior
No 1 Ashey

No 1 Ashey

No 1 Ashey
Ryde
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 5,032
AED 5,879 total
includes taxes & fees
10 Jan - 11 January 2026
No 1 Ashey
Outdoor spa tub
Dassia

Dassia

Dassia
Porchfield
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 3,365
AED 3,948 total
includes taxes & fees
22 Dec - 23 Dec
Dassia
Terrace/patio
Princes Esplanade

Princes Esplanade

Princes Esplanade
Gurnard
10.0 out of 10, Exceptional, (3)
"We loved the beautiful location"
United States
Susan
The price is AED 3,177
AED 3,863 total
includes taxes & fees
7 Jan - 8 January 2026
Princes Esplanade
Exterior
6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms

6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms

6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms
Emsworth
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 3,840
AED 3,840 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

St Georges Villa

St Georges Villa
Ryde
The price is AED 3,208
AED 3,750 total
includes taxes & fees
6 Jan - 7 January 2026
St Georges Villa
Exterior
Castle Cottage-Isle of Wight

Castle Cottage-Isle of Wight

Castle Cottage-Isle of Wight
Ryde
The price is AED 3,460
AED 4,027 total
includes taxes & fees
29 Dec - 30 Dec
Castle Cottage-Isle of Wight
Exterior
George Street House

George Street House

George Street House
Ryde
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 3,680
AED 4,269 total
includes taxes & fees
22 Dec - 23 Dec
George Street House
Outdoor dining
Penderic, Isle of Wight

Penderic, Isle of Wight

Penderic, Isle of Wight
Cowes
The price is AED 3,302
AED 3,952 total
includes taxes & fees
22 Dec - 23 Dec
Penderic, Isle of Wight
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

Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

10/10 Excellent
"Clean modern rooms and very pleasant professional staff."
Paula 1-night trip
Posted 2 days ago
Norton Park Hotel, Spa & Manor House