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Chalets in City of Winchester

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Top Cities in City of Winchester

A large stone castle with multiple towers and battlements.
ChaletsChalets

Southampton

Southampton

Our top choices for City of Winchester chalets

Dining

1. 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)
"Had a great time staying at this lovely Lodge Retreat. Would recommend."
United States
Penelope
3 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, (78 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
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 traveler
The price is AED 4,282
AED 4,981 total
includes taxes & fees
26 Sep - 27 Sep
York Street
TV

4. 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

5. 2 bedroom accommodation in Wootton Bridge, Nr Cowes

2 bedroom accommodation in Wootton Bridge, Nr Cowes
Wootton Bridge, Nr Cowes
9.6 out of 10, Exceptional, (21 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
Exterior

6. Coastal Country Park Holiday Home

Coastal Country Park Holiday Home
Downton
9.4 out of 10, Exceptional, (40 reviews)
"Lovely accommodation, great location for exploring the surrounding area. Brilliant communication with the owner"
United Kingdom
Helen L.
Coastal Country Park Holiday Home
Property grounds

7. Coastal East View

Coastal East View
St Helens
10.0 out of 10, Exceptional, (6 reviews)
"We really liked the property, very spacious kitchen and master bedroom. Liked that there were two bathrooms. The house and garden were great for dogs."
United States
Jo
Coastal East View
Exterior detail

8. 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
Outdoor dining

9. Colonels Rest

Colonels Rest
Sandown
9.8 out of 10, Exceptional, (33 reviews)
"Living space and decor.. also clean throughout, and great location"
United States
Nicki
The price is AED 5,447
AED 7,394 total
includes taxes & fees
22 Sep - 23 Sep
Colonels Rest
3 bedrooms, iron/ironing board, travel crib, WiFi

10. 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 traveler
Rural Lodge Retreat with Hot Tub
TV

11. 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
Fridge, oven, stovetop, dishwasher

12. 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, (30 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.
A heated pool

13. 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 AED 6,297
AED 7,517 total
includes taxes & fees
27 Sep - 28 Sep
Rookley Farm Lodge
TV

14. Carisbrooke Premier Lodge

Carisbrooke Premier Lodge
Wootton, Nr Cowes
9.4 out of 10, Exceptional, (14 reviews)
"Lovely lodge with everything we needed for our stay, the hot tub is a big plus and relaxing end to the day."
United States
DAVID
Carisbrooke Premier Lodge
Terrace/patio

15. North Quay

North Quay
St Helens
10.0 out of 10, Exceptional, (2 reviews)
"The property is amazing thank you, perfect for our holiday, everything we needed. Great facilities and beautiful decor."
United States
Dave Matthews
The price is AED 4,660
AED 5,495 total
includes taxes & fees
26 Sep - 27 Sep
North Quay
Coffee/tea maker, fridge, microwave, stovetop

16. 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 AED 345
AED 454 total
includes taxes & fees
27 Sep - 28 Sep
Hayling Hideaway, private self contained cosy annex near to beach
Exterior detail

17. 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
Outdoor dining

18. The Good Ships

The Good Ships
Shanklin
9.4 out of 10, Exceptional, (13 reviews)
"Perfect accomodation for 2. Clean, everything at hand. Quit location altough in the middle of Shanklin and only a few minutes walk to the sea. Wifi was a bit slow."
United States
Petra
The price is AED 2,204
AED 2,646 total
includes taxes & fees
28 Sep - 29 Sep
The Good Ships
Property grounds

19. Seagrass

Seagrass
Sandown
10.0 out of 10, Exceptional, (11 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 AED 4,062
AED 4,665 total
includes taxes & fees
20 Oct - 21 Oct
Seagrass
Exterior

20. 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 traveler
The price is AED 4,880
AED 5,860 total
includes taxes & fees
21 Oct - 22 Oct
No 1 Ashey
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

Moxy Southampton

Moxy Southampton

8/10 Good
"Clean room, convenient location, but the room is small, only one chair available to sit."
George 2-night trip
Posted 10 hours ago
Moxy Southampton

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