Winchester Chalets

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Winchester hotels

Chalets in Winchester

York Street

Cowes Isle of Wight

$1,328 nightly

$1,340 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

With a stay at this chalet in Cowes, you'll be a 4-minute walk from Cowes Harbour and 11 minutes by foot from Royal London Yacht Club.

Kitchen

Washer

Superb lodge with one master double and one twin.

Tilford, Farnham

With a stay at this chalet in Farnham, you'll be within a 10-minute drive of South Downs National Park and Hankley Common Golf Club.

Kitchen

Free WiFi

2 bedroom accommodation in Wootton Bridge, Nr Cowes

Wootton Bridge, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Kitchen

Carisbrooke Premier Lodge

Wootton, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Hot Tub

Kitchen

Sturt Watersedge Lodge

Tilford, Farnham

With a stay at this chalet in Farnham, you'll be within a 10-minute drive of South Downs National Park and Hankley Common Golf Club.

Free WiFi

3 bedroom accommodation in Wootton Bridge, Nr Cowes

Wootton Bridge, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Hot Tub

Kitchen

2 bedroom accommodation in Wootton Bridge, Nr Cowes

Wootton Bridge, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Hot Tub

Kitchen

2 bedroom accommodation in Wootton Bridge, Nr Cowes

Wootton Bridge, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Hot Tub

Kitchen

Secluded, New Forest Riverside Lodge

Godshill ENG

With a stay at this chalet in Fordingbridge, you'll be a 5-minute walk from New Forest National Park and within a 5-minute drive of Fordingbridge Town Hall.

Hot Tub

Kitchen

Middle Lodge

Ryde Isle of Wight

With a stay at this chalet in Ryde, you'll be a 4-minute walk from Appley Beach and 10 minutes by foot from Ryde Beach.

Kitchen

Washer

4 bedroom accommodation in Wootton Bridge, Nr Cowes

Wootton Bridge, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Hot Tub

Free WiFi

2 bedroom accommodation in Wootton Bridge, Nr Cowes

Wootton Bridge, Nr Cowes

With a stay at this chalet in Ryde, you'll be a 2-minute walk from Woodside Beach and 11 minutes by foot from Isle of Wight Area of Outstanding Natural Beauty.

Kitchen

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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.