A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

Search Chalets in Winchester from CA $1,374

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winchester chalets

Outdoor spa tub

1. Dassia

Dassia
Porchfield
9.6 out of 10, Exceptional, (4 reviews)
"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
Dassia
Terrace/patio

2. Creek View, Isle of Wight

Creek View, Isle of Wight
Wootton Bridge
10.0 out of 10, Exceptional, (4 reviews)
"A truly amazing stay at a wonderful location. A superb home to base an island adventure! VRBO"
United States
Benjamin Gully
The price is CA $2,414
CA $2,797 total
includes taxes & fees
Aug 2 - Aug 3
Creek View, Isle of Wight
Exterior

3. York Street

York Street
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"It was absolutely perfect ! The house was so well looked after ."
United States
Anonymous traveller
The price is CA $1,633
CA $1,901 total
includes taxes & fees
Sep 1 - Sep 2
York Street
Exterior

4. 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, (87 reviews)
"A brilliantly equipped, welcoming lodge with lots of nature to enjoy, including a swan pair outside. Warm and comfortable with great amenities"
United States
Anonymous traveller
The price is CA $1,924
CA $1,924 total
includes taxes & fees
Aug 14 - Aug 15
6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms
Exterior

5. George Street House

George Street House
Ryde
8.0 out of 10, Very good, (2 reviews)
"Customer service was excellent with no problems, the process was vey efficient. The house was very clean and in a perfect spot for our stay, would highly recommend."
United States
Kay
The price is CA $1,331
CA $1,606 total
includes taxes & fees
Sep 1 - Sep 2
George Street House
Exterior

6. St Georges Villa

St Georges Villa
Ryde
The price is CA $1,234
CA $1,499 total
includes taxes & fees
Aug 31 - Sep 1
St Georges Villa
Exterior

7. No 1 Ashey

No 1 Ashey
Ryde
9.4 out of 10, Exceptional, (18 reviews)
"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 traveller
The price is CA $6,036
CA $6,828 total
includes taxes & fees
Aug 18 - Aug 19
No 1 Ashey
Outdoor dining

8. Penderic, Isle of Wight

Penderic, Isle of Wight
Cowes
The price is CA $1,137
CA $1,374 total
includes taxes & fees
Sep 1 - Sep 2
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

The Winchester Hotel & Spa

The Winchester Hotel & Spa

8/10 Good
"Was a bit hot, but lovely biscuits"
Sam 1-night trip
Posted 4 hours ago
The Winchester Hotel & Spa

Find out more about Winchester

Winchester Chalets information

Number of reviews
123
Accommodation
127 Chalets
Lowest Price
CA $1,374
Highest Price
CA $6,828