Book Holiday Homes in Winchelsea

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Winchelsea

Secluded Farmhouse set in 300 acres, sleeps 11 comfortably, and up to 14 people.

Secluded Farmhouse set in 300 acres, sleeps 11 comfortably, and up to 14 people.

Battle
Stay at this vacation home in Battle. Enjoy free WiFi, a water park, and a garden. Popular attractions Battle Golf Club and Gardens and Battle Museum of Local ...
Secluded Farmhouse set in 300 acres, sleeps 11 comfortably, and up to 14 people.
Pine Cabin Overlooking Bedgebury Forest

Pine Cabin Overlooking Bedgebury Forest

Goudhurst
The price is NZ$351 per night from 4 Apr to 5 Apr
NZ$351
includes taxes & fees
4 Apr - 5 Apr
Stay at this vacation home in Cranbrook. Popular attractions Bedgebury National Pinetum and Forest and Go Ape at Bedgebury are located nearby.
Pine Cabin Overlooking Bedgebury Forest
KINARA in CAMBER. 5-BED DESIGNED HOUSE BY THE SEA.

KINARA in CAMBER. 5-BED DESIGNED HOUSE BY THE SEA.

Camber
Book a stay at this family-friendly vacation home in Rye. Enjoy free WiFi, a garden, and patios. Popular attractions Camber Sands and Rye Golf Club are located ...
KINARA in CAMBER. 5-BED DESIGNED HOUSE BY THE SEA.
Save an average of 15% on thousands of hotels when you're signed in
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
Book a stay at this family-friendly vacation home in Cranbrook. Enjoy private pools, a garden, and in-room fireplaces. Popular attractions Hole Park Gardens ...
Lower Standen Farm by Bloom stays that sleeps 24 guests in 9 bedrooms
Spacious 3 Bed House In Ashford with En-Suite

Spacious 3 Bed House In Ashford with En-Suite

Ashford
Stay at this vacation home in Ashford. Popular attractions Hollywood Bowl and St Mary The Virgin Church are located nearby.
Spacious 3 Bed House In Ashford with En-Suite
Quiet Location In The Heart Of Eastbourne

Quiet Location In The Heart Of Eastbourne

Eastbourne
Book a stay at this family-friendly vacation home in Eastbourne. Enjoy a water park, cable/satellite TV service, and an in-room coffeemaker. Popular attractions ...
Quiet Location In The Heart Of Eastbourne
76 The Mint - Four Bedroom House, Sleeps 6

76 The Mint - Four Bedroom House, Sleeps 6

Rye
The price is NZ$1,495 per night from 26 Apr to 27 Apr
NZ$1,495
includes taxes & fees
26 Apr - 27 Apr
Stay at this vacation home in Rye. Enjoy free WiFi, a garden, and patios. Popular attractions Camber Sands and Lamb House are located nearby.
76 The Mint - Four Bedroom House, Sleeps 6
Oastbrook Estate Vineyard

Oastbrook Estate Vineyard

3.5 out of 5
Park Farm Oast, Robertsbridge, England
Stay at this vacation home in Robertsbridge. Enjoy parking (surcharge), a garden, and a picnic area. Popular attractions Merriments Gardens and Bodiam Castle ...
Oastbrook Estate Vineyard
Romantic glamping cabin near beautiful Rye

Romantic glamping cabin near beautiful Rye

Winchelsea
Stay at this vacation home in Winchelsea. Enjoy a garden and patios. Popular attractions Mallydams Woods and Pett Level Beach are located nearby.
Romantic glamping cabin near beautiful Rye
Don't see what you're looking for?
See all available properties in Winchelsea
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.

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
465 Holiday Homes
Lowest Price
NZ$121
Highest Price
NZ$1,495
Popular accommodation
Secluded Farmhouse set in 300 acres, sleeps 11 comfortably, and up to 14 people., Pine Cabin Overlooking Bedgebury Forest, KINARA in CAMBER. 5-BED DESIGNED HOUSE BY THE SEA., Lower Standen Farm by Bloom stays that sleeps 24 guests in 9 bedrooms, Spacious 3 Bed House In Ashford with En-Suite, Quiet Location In The Heart Of Eastbourne, 76 The Mint - Four Bedroom House, Sleeps 6, Oastbrook Estate Vineyard, Romantic glamping cabin near beautiful Rye

Top trending hotels in Winchelsea

Winchelsea Lodge

Winchelsea Lodge

3 out of 5
Hastings Road, Winchelsea, England
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 4 Apr to 5 Apr
NZ$201
includes taxes & fees
4 Apr - 5 Apr
Stay at this 3-star hotel in Winchelsea. Enjoy free parking, breakfast (surcharge), and a business center. Popular attractions Camber Sands and Church of St ...
Winchelsea Lodge
The Burlington Hotel

The Burlington Hotel

3 out of 5
Grand Parade, Eastbourne, England
Fully refundableReserve now, pay when you stay
The price is NZ$121 per night from 27 Apr to 28 Apr
NZ$121
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3-star hotel in Eastbourne. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the convenient ...
The Burlington Hotel
Hythe Imperial Hotel Spa & Golf

Hythe Imperial Hotel Spa & Golf

4 out of 5
Princes Parade, Hythe, England
Fully refundableReserve now, pay when you stay
The price is NZ$150 per night from 21 Apr to 22 Apr
NZ$150
includes taxes & fees
21 Apr - 22 Apr
Stay at this 4-star beach hotel in Hythe. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular ...
Hythe Imperial Hotel Spa & Golf
Save an average of 15% on thousands of hotels when you're signed in
The View Hotel

The View Hotel

3 out of 5
Grand Parade, East Sussex, Eastbourne, England
Fully refundable
The price is NZ$172 per night from 6 Apr to 7 Apr
NZ$172
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star business-friendly hotel in Eastbourne. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the breakfast and the helpful ...
The View Hotel
Don't see what you're looking for?
See all available properties in Winchelsea
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.