A cathedral at night with illuminated trees and a park with benches.

Chalets in City of Winchester

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

City of Winchester Accommodation: Most Popular Cities to Stay

A large stone castle with multiple towers and battlements.
ChaletsChalets

Southampton

Southampton

Our top choices for City of Winchester chalets

TV

1. 2 bedroom accommodation in Wootton Bridge, Nr Cowes

2 bedroom accommodation in Wootton Bridge, Nr Cowes
Wootton Bridge, Nr Cowes
9.4 out of 10, Exceptional, (34 reviews)
"Perfect for a base to explore the island, nice quite veranda that we use for breakfast or just cup's of tea when we could home."
United States
Ian
2 bedroom accommodation in Wootton Bridge, Nr Cowes
Beach

2. WELL POSITIONED CHALET IN SANDOWN with broadband

WELL POSITIONED CHALET IN SANDOWN with broadband
Sandown
9.8 out of 10, Exceptional, (74 reviews)
"This property is in a nice location close to the beach. There’s everything you could possibly need in the chalet. I liked the welcome we received very thoughtful and was very much appreciated. Car parking is there too . We will definitely be returning."
United Kingdom
Debra
WELL POSITIONED CHALET IN SANDOWN with broadband
Dining

3. 3 bedroom accommodation in Wootton Bridge, Nr Cowes

3 bedroom accommodation in Wootton Bridge, Nr Cowes
Wootton Bridge, Nr Cowes
9.4 out of 10, Exceptional, (38 reviews)
"Lovely lodge, homely, comfy with everything you need."
United States
Julie
3 bedroom accommodation in Wootton Bridge, Nr Cowes
Exterior detail

4. Seawinds Chalet holidays by the sea

Seawinds Chalet holidays by the sea
Sandown
9.8 out of 10, Exceptional, (12 reviews)
"It's a very good place to stay with family, we enjoyed our stay at this property. Liza was very helpful and accommodating."
United Kingdom
Mohammed R.
Seawinds Chalet holidays by the sea
Exterior

5. 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 £1,005
includes taxes & fees
1 Sept - 2 Sept
York Street
TV

6. Sturt Watersedge Lodge

Sturt Watersedge Lodge
Tilford, Farnham
9.6 out of 10, Exceptional, (5 reviews)
"Great location next to the duck pond and very quiet and secluded.Lodge had everything you could need for a break away and extremely clean . The furniture is a little dated but, that did not distract from a very comfortable stay . Near to a love golf course with fantastic views and a good pub next door . Very good base for exploring all that the area has to offer ."
United States
Jeanette
Sturt Watersedge Lodge
Exterior

7. 2 bedroom accommodation in Wootton Bridge, Nr Cowes

2 bedroom accommodation in Wootton Bridge, Nr Cowes
Wootton Bridge, Nr Cowes
9.4 out of 10, Exceptional, (20 reviews)
"A lovely spotlessly clean spacious lodge in idyllic setting. Everything you need for a stay. Will certainly book again."
United States
Maggie
2 bedroom accommodation in Wootton Bridge, Nr Cowes
Terrace/patio

8. North Quay

North Quay
St Helens
10.0 out of 10, Exceptional, (1 review)
"Beautifully furnished and in good decorative order. Loads of space, really well-equipped kitchen, comfy beds. There was a big box of toys for the little ones to play with, as well as baby gates, a travel cot and other useful things for kids. It was the ideal location for our trip. Nothing at all, it was all great!"
United States
Lauren
The price is £1,215
includes taxes & fees
2 Sept - 3 Sept
North Quay
Exterior

9. Coastal Country Park Holiday Home

Coastal Country Park Holiday Home
Downton
9.4 out of 10, Exceptional, (38 reviews)
"Lovely accommodation, great location for exploring the surrounding area. Brilliant communication with the owner"
United Kingdom
Helen L.
Coastal Country Park Holiday Home
TV

10. 4 bedroom accommodation in Wootton Bridge, Nr Cowes

4 bedroom accommodation in Wootton Bridge, Nr Cowes
Wootton Bridge, Nr Cowes
8.8 out of 10, Excellent, (10 reviews)
"Fabulous accommodation. So comfortable."
United States
Sue
4 bedroom accommodation in Wootton Bridge, Nr Cowes
A heated pool

11. Rookley Farm Lodge

Rookley Farm Lodge
Rookley
10.0 out of 10, Exceptional, (11 reviews)
"Great house in an excellent location in the centre of the island - very easy to get anywhere you might want to go!"
United States
Patrick
The price is £3,640
includes taxes & fees
4 Sept - 5 Sept
Rookley Farm Lodge
Exterior

12. 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 £1,529
includes taxes & fees
6 Sept - 7 Sept
No 1 Ashey
3 bedrooms, iron/ironing board, travel cot, WiFi

13. Rural Lodge Retreat with Hot Tub

Rural Lodge Retreat with Hot Tub
Chichester
10.0 out of 10, Exceptional, (4 reviews)
"We had a fantastic stay - beautiful surroundings, fantastic facilities and great hot tub to relax in. Would definitely stay again. Lovely friendly owners too. Thanks for a great break. "
United States
Anonymous traveller
Rural Lodge Retreat with Hot Tub
Chalet | Exterior

14. Free Ferry on 7 Days Bookings Jul/aug

Free Ferry on 7 Days Bookings Jul/aug
3.0 star property
Cowes
8.0 out of 10, Very good, (1 review)
"Clean and family accommodation, The facilities such as restaurant. swimming pool, retail shop and children play area are very close to the property."
United Kingdom
Shanmugavadivelu
Free Ferry on 7 Days Bookings Jul/aug
TV

15. Carisbrooke Premier Lodge

Carisbrooke Premier Lodge
Wootton, Nr Cowes
9.4 out of 10, Exceptional, (14 reviews)
"Loved it x great site lodge was clean friendly staff lodges were all private no looking over anybody else and secluded beach with amazing rockpooling at low tide 👌"
United States
Karen
Carisbrooke Premier Lodge
Exterior detail

16. Simeon Sands Coastal Escape

Simeon Sands Coastal Escape
Ryde
10.0 out of 10, Exceptional, (1 review)
"This place was spot on, the house had everything we needed and more. Downstairs toilet would come in handy, but not the end of the world."
United States
Francesca
Simeon Sands Coastal Escape
Coffee/tea maker, fridge, microwave, stovetop

17. Hayling Hideaway, private self contained cosy annex near to beach

Hayling Hideaway, private self contained cosy annex near to beach
Hayling Island
9.6 out of 10, Exceptional, (4 reviews)
"All was perfect. "
United Kingdom
Ricchard B.
The price is £95
includes taxes & fees
18 Aug - 19 Aug
Hayling Hideaway, private self contained cosy annex near to beach
Property grounds

18. Seagrass

Seagrass
Sandown
10.0 out of 10, Exceptional, (10 reviews)
"The property is excellent a great Christmas stay. Thank you so much for the lovely decorations and treats. Can’t wait to come back."
United States
Sharon
The price is £850
includes taxes & fees
31 Aug - 1 Sept
Seagrass
Terrace/patio

19. Bunny lodge- Luxury Lodge with decking- Pool & Spa Access

Bunny lodge- Luxury Lodge with decking- Pool & Spa Access
Downton
Bunny lodge- Luxury Lodge with decking- Pool & Spa Access
TV

20. Superb lodge with one master double and one twin.

Superb lodge with one master double and one twin.
Tilford, Farnham
9.4 out of 10, Exceptional, (29 reviews)
"Great accommodation in a fantastic area. Couldn't ask for anything more!"
United States
Martin
Superb lodge with one master double and one twin.
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 City of Winchester Hotel Reviews

The Winchester Hotel & Spa

The Winchester Hotel & Spa

10/10 Excellent
"Sim, the receptionist was awesome!"
Horacio 1-night trip
Posted 3 hours ago
The Winchester Hotel & Spa

Find out more about City of Winchester

City of Winchester Chalets information

Number of reviews
238
Accommodation
257 Chalets
Lowest Price
£95
Highest Price
£3,640

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