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

Large House, Contractors, Families, Free Parking

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

Pass the Keys | Luxury Lakeside Lodge

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

Spacious 3-bedroom bungalow with hot tub, 3 mins to beach

Romantic glamping cabin near beautiful Rye

Quiet Location In The Heart Of Eastbourne

70s Inspired, 3-Bed Home in Rye with river views

Charming countryside retreat
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 | 486 Holiday Homes |
---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Large House, Contractors, Families, Free Parking, Cozy converted millking barn in the weald of Kent, 50mins from Central London, Pass the Keys | Luxury Lakeside Lodge, Lower Standen Farm by Bloom stays that sleeps 24 guests in 9 bedrooms, Spacious 3-bedroom bungalow with hot tub, 3 mins to beach, Romantic glamping cabin near beautiful Rye, Quiet Location In The Heart Of Eastbourne, 70s Inspired, 3-Bed Home in Rye with river views, Charming countryside retreat |
Top trending hotels in Winchelsea

Winchelsea Lodge

Hythe Imperial Hotel Spa & Golf

The View Hotel

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