Book Holiday Homes in Winchelsea

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Featured Holiday Homes in Winchelsea

Beautiful Countryside cottage

Beautiful Countryside cottage

Ashford
Located in Ashford, this vacation home is within a 10-minute drive of St. Michael the Archangel and Chart Hills Golf Club.
Beautiful Countryside cottage
Converted barn / Oast House with amazing views and EV chargers

Converted barn / Oast House with amazing views and EV chargers

Rye
Located in Rye, this vacation home is in a rural location, within a 10-minute drive of Carr Taylor Vineyard and High Weald.
Converted barn / Oast House with amazing views and EV chargers
Trees Annex - Bexhill

Trees Annex - Bexhill

Bexhill
Located in Bexhill-on-Sea, this vacation home is within a 5-minute drive of Highwoods Golf Club and Egerton Park.
Trees Annex - Bexhill
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The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel

The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel

Hythe
The price is AU$432 per night from 29 Aug to 30 Aug
AU$432
29 Aug - 30 Aug
includes taxes & fees
With a stay at this vacation home in Hythe, you'll be within a 10-minute drive of Port Lympne Wild Animal Park and Gardens and St Leonard's Church.
The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel
Quiet Location In The Heart Of Eastbourne

Quiet Location In The Heart Of Eastbourne

Eastbourne
With a stay at this vacation home, you'll be centrally located in Eastbourne, within a 5-minute drive of South Downs National Park and Eastbourne Town Hall.
Quiet Location In The Heart Of Eastbourne
Lower Standen Farm by Bloom stays that sleeps 24 guests  in 9 bedrooms

Lower Standen Farm by Bloom stays that sleeps 24 guests in 9 bedrooms

Benenden
Located in Cranbrook, this vacation home is in a rural location, within a 10-minute drive of Morgan Museum and Hole Park Gardens.
Lower Standen Farm by Bloom stays that sleeps 24 guests in 9 bedrooms
Barn conversion in beautiful, peaceful, rural location with stunning views.

Barn conversion in beautiful, peaceful, rural location with stunning views.

Hailsham
Located in Hailsham, this vacation home is in a rural location, within a 10-minute drive of High Weald and Blackstock Farm.
Barn conversion in beautiful, peaceful, rural location with stunning views.
Cozy converted millking barn in the weald of Kent, 50mins from Central London

Cozy converted millking barn in the weald of Kent, 50mins from Central London

Great Chart
With a stay at this vacation home in Ashford, you'll be within a 5-minute drive of Great Chart Golf and Leisure and The Reindeer Centre.
Cozy converted millking barn in the weald of Kent, 50mins from Central London
Large House, Contractors, Families, Free Parking

Large House, Contractors, Families, Free Parking

Ashford
With a stay at this vacation home in Ashford, you'll be within a 15-minute drive of Port Lympne Wild Animal Park and Gardens and Ashford Golf Club.
Large House, Contractors, Families, Free Parking
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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.

Winchelsea Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchelsea vacation homes are the perfect way for you to wing it.

Holiday houses in Winchelsea let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchelsea in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchelsea adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchelsea with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchelsea vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchelsea Holiday Homes essential information

Accommodation
471 Holiday Homes
Lowest Price
AU$101
Highest Price
AU$432
Popular accommodation
Beautiful Countryside cottage, Converted barn / Oast House with amazing views and EV chargers, Trees Annex - Bexhill, The Bolt Hole Hythe panoramic sea views, parking, garden, 5 min to eurotunnel, Quiet Location In The Heart Of Eastbourne, Lower Standen Farm by Bloom stays that sleeps 24 guests in 9 bedrooms, Barn conversion in beautiful, peaceful, rural location with stunning views., Cozy converted millking barn in the weald of Kent, 50mins from Central London, Large House, Contractors, Families, Free Parking

Top trending hotels in Winchelsea

Winchelsea Lodge

Winchelsea Lodge

3 out of 5
Hastings Road, Winchelsea, England
The price is AU$229 per night from 10 Sept to 11 Sept
AU$229
10 Sept - 11 Sept
includes taxes & fees
With a stay at Winchelsea Lodge in Winchelsea, you'll be within a 15-minute drive of Camber Sands and Church of St Thomas a Becket.
Winchelsea Lodge
The New Inn

The New Inn

4 out of 5
German Street, Winchelsea, England
Fully refundableReserve now, pay when you stay
The price is AU$292 per night from 26 Aug to 27 Aug
AU$292
26 Aug - 27 Aug
includes taxes & fees
With a stay at The New Inn in Winchelsea, you'll be within a 15-minute drive of Camber Sands and Church of St Thomas a Becket.
The New Inn
The Burlington Hotel

The Burlington Hotel

3 out of 5
Grand Parade, Eastbourne, England
Fully refundableReserve now, pay when you stay
The price is AU$101 per night from 31 Aug to 1 Sept
AU$101
31 Aug - 1 Sept
includes taxes & fees
With a stay at The Burlington Hotel in Eastbourne (Eastbourne City Centre), you'll be within a 5-minute drive of South Downs National Park and Eastbourne ...
The Burlington Hotel
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Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Simone Weil Avenue, Ashford, England
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 21 Sept to 22 Sept
AU$146
21 Sept - 22 Sept
includes taxes & fees
With a stay at Ashford International Hotel & Spa in Ashford, you'll be within a 15-minute drive of Port Lympne Wild Animal Park and Gardens and Ashford Golf ...
Ashford International Hotel & Spa
Don't see what you're looking for?
See all available properties in Winchelsea
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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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^Subject to availability and chosen travel dates.