Winchelsea Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Winchelsea vacation rentals

Exterior
Sparrows Den Lodge

Vacation Home in Winchelsea

Sparrows Den Lodge
3.5 star property
The price is P24,816
P29,779 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sparrows Den Lodge
Garden
Pinewood Camping Pods - At Port Lympne Reserve

Camping in Hythe

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.4 out of 10, Exceptional, (30)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is P10,056
P12,067 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Pinewood Camping Pods - At Port Lympne Reserve
Free WiFi
Osborne Apartments

Aparthotel in Eastbourne

Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (92)
"great staff and facilities"
United Kingdom
Martin
Osborne Apartments
Miscellaneous
Bexlet

Apartment in Bexhill-on-Sea

Bexlet
2.0 star property
8.6 out of 10, Excellent, (50)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is P5,223
P6,268 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bexlet
Interior
Gun Hill Cottage

Cottage in Heathfield

Gun Hill Cottage
3.5 star property
10.0 out of 10, Exceptional, (2)
"Gun Hill Cottage is a truly charming little place, really clean, nicely decorated, with everything you need. Chris was an amazing host, let us know all the details in advance, then checked in by email that everything was good. we really enjoyed our stay. Thanks! Tom"
United Kingdom
Thomas
The price is P48,553
P58,264 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Gun Hill Cottage
Garden
Calm Private Annex Ideal to Work, Rest & Explore

Apartment in Ashford

Calm Private Annex Ideal to Work, Rest & Explore
2.0 star property
The price is P6,340
P7,608 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Calm Private Annex Ideal to Work, Rest & Explore
Property grounds
Lilyrose Cottage

Cottage in Pevensey

Lilyrose Cottage
3.0 star property
10.0 out of 10, Exceptional, (1)
"All very good. However too many disabled parking spaces meaning too few for others"
United Kingdom
Graeme
The price is P29,267
P35,120 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Lilyrose Cottage
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 Winchelsea Hotel Reviews

The View Hotel

The View Hotel

10/10 Excellent
"Comfortable bed, large clean room, friendly staff, buffet breakfast very good. "
Bryan 2-night trip
Posted 3 days ago
The View Hotel

Find out more about Winchelsea

Search for holiday rentals in Winchelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchelsea using one of the methods below:

  • View our selection of featured holiday rentals in Winchelsea
  • Use the map to find apartments and other holiday homes in the Winchelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchelsea while they last

Look no further and take a look at our great range of rental properties in Winchelsea!

Frequently asked questions

Can I find vacation rentals in Winchelsea?

Yes, we have vacation rentals near well known local attractions in Winchelsea, or you can select a more secluded option if you're looking for relaxation. Our travelers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

How many vacation rentals are there in Winchelsea?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Winchelsea stay.

What’s there to see and do in Winchelsea?

Winchelsea Beach and High Weald are a couple of lovely local spots to get outside and enjoy nature. Pett Level Beach and St. Thomas the Martyr are other places to visit while you're in town.

What’s a vacation rental in Winchelsea like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchelsea. Vacation rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.