A historic church with a stone pathway leading to its entrance, surrounded by a cemetery with numerous headstones.

Winchelsea Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchelsea vacation rentals

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is CA $646
CA $775 total
includes taxes & fees
Jul 9 - Jul 10
Sparrows Den Lodge

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (54 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is CA $141
CA $169 total
includes taxes & fees
Jul 6 - Jul 7
Bexlet

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (3 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is CA $119
CA $142 total
includes taxes & fees
Jul 6 - Jul 7
Chestnut Meadow Camping

Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (43 reviews)
"A stunningly beautiful setting. Clean, tidy and, elegantly decorated and set out. Secure, peaceful and comfortable. We shall most definitely stay there again. Cannot recommend highly enough! ✨💫✨💫✨💫💚🌲💚💫✨💫✨"
United Kingdom
Diana
The price is CA $271
CA $271 total
includes taxes & fees
Jul 6 - Jul 7
Extraordinary Huts

3 Seaview Cottages

3 Seaview Cottages
2.0 star property
Pevensey
The price is CA $583
CA $700 total
includes taxes & fees
Jul 10 - Jul 11
3 Seaview Cottages

Suspire House -sleeps6-garden-bbq-coastal Retreat

Suspire House -sleeps6-garden-bbq-coastal Retreat
3.0 star property
New Romney
The price is CA $250
CA $391 total
includes taxes & fees
Jul 6 - Jul 7
Suspire House -sleeps6-garden-bbq-coastal Retreat

Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (114 reviews)
"Spacious and quiet property in a ideal location close to the beach."
United Kingdom
narendrakumar
The price is CA $101
CA $121 total
includes taxes & fees
Jul 19 - Jul 20
Osborne Apartments

Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.6 out of 10, Exceptional, (37 reviews)
"Great location we could see the lions from our room! Only slight downside was the sofa bed was a little on the uncomfortable side, but we had a great time and the staff were great too."
United Kingdom
Steve
The price is CA $333
CA $400 total
includes taxes & fees
Jul 8 - Jul 9
Pinewood Camping Pods - At Port Lympne Reserve

Oastbrook Glamping

Oastbrook Glamping
2.0 star property
Robertsbridge
10.0 out of 10, Exceptional, (1 review)
"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."
United Kingdom
Sima
The price is CA $300
CA $360 total
includes taxes & fees
Jul 6 - Jul 7
Oastbrook Glamping

Salthaven Shepherds Hut

Salthaven Shepherds Hut
2.0 star property
Pevensey
10.0 out of 10, Exceptional, (1 review)
"Beautiful and homely hut! Has everything you need for a relaxing get away. The garden is much larger than I thought as well as being enclosed for dogs! The hosts were really lovely, great communication and welcoming."
United Kingdom
Nicola
The price is CA $477
CA $572 total
includes taxes & fees
Jul 10 - Jul 11
Salthaven Shepherds Hut

Caravan - Sleeps 8 - Pets Ok - Parking - Patio

Caravan - Sleeps 8 - Pets Ok - Parking - Patio
3.0 star property
Rye
4.0 out of 10, (2 reviews)
"I was disappointed with this stay. For the amount of money it cost, the caravan was not clean, was overcrowded and needs a lot of smarting up. You had to pay extra to have bedding which I think is unreasonable, particularly how much it cost per night anyway. Communication with the host was fine but not great. Unfortunately I won’t be recommending or returning to this property. "
United Kingdom
Kerry
The price is CA $251
CA $346 total
includes taxes & fees
Jul 19 - Jul 20
Caravan - Sleeps 8 - Pets Ok - Parking - Patio

2 Seaview Cottages

2 Seaview Cottages
2.0 star property
Pevensey
The price is CA $607
CA $729 total
includes taxes & fees
Jul 21 - Jul 22
2 Seaview Cottages

2-bed, Sleeps 4, Free Parking, Pets Allowed

2-bed, Sleeps 4, Free Parking, Pets Allowed
3.0 star property
Eastbourne City Centre
The price is CA $505
CA $505 total
includes taxes & fees
Aug 3 - Aug 4
2-bed, Sleeps 4, Free Parking, Pets Allowed

South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
The price is CA $751
CA $901 total
includes taxes & fees
Jul 16 - Jul 17
South Beach Landings 0028

Pet Friendly Private Cabin Town Eurotunnel Beach

Pet Friendly Private Cabin Town Eurotunnel Beach
3.0 star property
Hythe
8.0 out of 10, Very good, (3 reviews)
"The closeness to the High St. meant it was easy to walk to find something to eat/drink. The host was very helpful."
United Kingdom
David
The price is CA $117
CA $140 total
includes taxes & fees
Jul 21 - Jul 22
Pet Friendly Private Cabin Town Eurotunnel Beach

The Seven Sands

The Seven Sands
3.0 star property
Romney Marsh
The price is CA $841
CA $1,009 total
includes taxes & fees
Jul 16 - Jul 17
The Seven Sands

Standard Hill Cottage

Standard Hill Cottage
2.0 star property
Battle
9.0 out of 10, Wonderful, (2 reviews)
"Very quiet and peaceful. Garden well maintained."
United Kingdom
Neil
The price is CA $519
CA $623 total
includes taxes & fees
Jul 11 - Jul 12
Standard Hill Cottage

Vine Cottage

Vine Cottage
3.5 star property
Tenterden
The price is CA $906
CA $1,087 total
includes taxes & fees
Jul 10 - Jul 11
Vine Cottage

Flat 4 - Penthouse

Flat 4 - Penthouse
3.0 star property
Hythe
The price is CA $1,051
CA $1,261 total
includes taxes & fees
Jul 9 - Jul 10
Flat 4 - Penthouse

Green Bank

Green Bank
2.0 star property
Romney Marsh
The price is CA $793
CA $951 total
includes taxes & fees
Jul 8 - Jul 9
Green Bank
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchelsea Hotel Reviews

Find out more about Winchelsea

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchelsea. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.

What's the top vacation rental that Winchelsea has to offer?

Romantic retreat in the hop fields of Kent, with great sightseeing: This vacation home near Winchelsea is located in the city center and has a patio, a garden, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winchelsea?

With 13 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.