Photo by John Scale

Holiday Rentals in Winchelsea

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

This weekend
Next weekend

Holiday Rentals in Winchelsea

A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
10.0 out of 10, Exceptional, (28)
"Loved this place, fantastic value for money, beautiful walks, lovely people, great facilities quiet and relaxing."
United Kingdom
Katy T.
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (87)
"JUST FANTASTIC check in - Shree was SO helpful and showed us our room and how to check out. It was incredible service. Loved the room, the kitchen and it was just wonderful. Will be staying again soon."
United Kingdom
Lucy
Osborne Apartments
Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.4 out of 10, Exceptional, (29)
"We had a lovely stay here, introducing our little boy to camping for the first time. It was a lovely and cosy pod for the 3 of us and it was amazing being right next to the lions. We loved toasting marshmallows by the fire pits & all the on site restaurants were lovely and delicious food. We had a great time. "
United Kingdom
Ann
The price is €163
includes taxes & fees
5 Nov - 6 Nov
Pinewood Camping Pods - At Port Lympne Reserve
Extraordinary Huts
3.0 star property
9.6 out of 10, Exceptional, (40)
"Really unique stay, lovely views."
United Kingdom
Louise
The price is €162
includes taxes & fees
19 Nov - 20 Nov
Extraordinary Huts
16th Century Cottage Situated Opposite The Medieval Landgate Arch
9.4 out of 10, Exceptional, (187)
"The property lies right in the heart of a very cute town. Enjoyed our stay"
United Kingdom
Darius M.
16th Century Cottage Situated Opposite The Medieval Landgate Arch
Coastguard Cottage With Sea Views
9.8 out of 10, Exceptional, (80)
"Fantastic location in the countryside, it was a lovely cottage in stunning scenery"
United Kingdom
Catherine S.
Coastguard Cottage With Sea Views
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.
10.0 out of 10, Exceptional, (17)
"Always a great stay at Heron Cottage, this was our 5th stay so this must prove we love it!"
United Kingdom
mark b.
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
"We had a very pleasant stay at this spacious and comfortable home, which was well-suited for our larger group. The garden was a particular highlight, offering ample space and the added delight of fresh fruit to pick. The location is great, being within a short walking distance of the beach and sea (20mins). The property was generally tidy, there were a few spiderwebs which luckily didn't have any spiders. If these were removed it would enhance the experience. Parking proved somewhat challenging...
United Kingdom
Tabassum A.
The price is €336
includes taxes & fees
6 Nov - 7 Nov
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
Bexlet
2.0 star property
8.6 out of 10, Excellent, (50)
"Easy to find on Sat Nav, parking nearby, very light, warm and comfortable, bed a little hard for us oldies. Overall great. Thank you"
United Kingdom
Ann
The price is €87
includes taxes & fees
17 Nov - 18 Nov
Bexlet
Tranquil Loft Apartment Overlooking Countryside
3.0 star property
10.0 out of 10, Exceptional, (1)
Tranquil Loft Apartment Overlooking Countryside
East Sussex Manor | Sleeps 12 | Hot Tub & Parking
The price is €305
includes taxes & fees
5 Nov - 6 Nov
East Sussex Manor | Sleeps 12 | Hot Tub & Parking
The Stables at Boreham House
5.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely stay at the stables. They have been converted to a high standard and were very comfortable for our family with two small children. It was great that there was a stair gate in the top bedroom as there isn’t a door. Had a nice meal at the local pub and in easy reach by car of local visiting sites. The hosts were very helpful and friendly and let us wander around their lovely garden. Would recommend. "
United Kingdom
Clement
The Stables at Boreham House
Extra-large luxury Shepherd's Hut, private hot tub, Smart TV, wifi, fab views.
10.0 out of 10, Exceptional, (15)
"We had a really lovely weekend away, was very peaceful and quiet. Sam was a great host, good communication before we arrived and helped show us around☺️ would definitely stay again. "
United Kingdom
Keira
Extra-large luxury Shepherd's Hut, private hot tub, Smart TV, wifi, fab views.
Beach Lodge - 5 minute walk to the sandy beach
8.8 out of 10, Excellent, (9)
"Fantastic lodge near the beach on a great location in the park. Highly recommend "
United Kingdom
Laura J.
The price is €265
includes taxes & fees
16 Nov - 17 Nov
Beach Lodge - 5 minute walk to the sandy beach
1-bedroom Apartment Sleeps 4, Parking
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is €150
includes taxes & fees
14 Nov - 15 Nov
1-bedroom Apartment Sleeps 4, Parking
Big2vacation Exclusive Camber Sands Holiday Park
3.0 star property
The price is €241
includes taxes & fees
19 Nov - 20 Nov
Big2vacation Exclusive Camber Sands Holiday Park
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
7.6 out of 10, Good, (9)
"Maria was an excellent host . There when we could not get hot tub started . Check in super easy. Good kitchen facilities. Wi fi . The tennis court was the greatest success. We were a family of 12 . 6adults 6children .What a grand house it was. It was a little dated and the Xmas decs tickled us in Aug .but the property was really lovely . Dated and maybe a little run down in places. Not very friendly with two year old as there were a lot of wires exposed in main TV room . There was a pond that we...
United Kingdom
Ann L.
The price is €591
includes taxes & fees
5 Nov - 6 Nov
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
Gun Hill Cottage
3.5 star property
10.0 out of 10, Exceptional, (2)
"Dit was zo’n beetje het mooiste huisje wat we ooit in Engeland hebben gehoord. Prachtige tuin, een droomhuisje! "
Netherlands
Ton & Liesbeth
The price is €838
includes taxes & fees
13 Nov - 14 Nov
Gun Hill Cottage
Cozy Camber Caravan 3 Bedroom Retreat With Decking
3.0 star property
4.0 out of 10, (2)
"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 €174
includes taxes & fees
18 Nov - 19 Nov
Cozy Camber Caravan 3 Bedroom Retreat With Decking
Outstanding luxury beachfront holiday experience with hot tub
10.0 out of 10, Exceptional, (111)
"Had the most amazing stay at the beach house with my family. It’s perfect for a large group. Amazing sea views and the hot tub was the best! We will be back. "
United Kingdom
Fleur H.
Outstanding luxury beachfront holiday experience with hot tub
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

Everything you need to know about Winchelsea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchelsea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchelsea holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchelsea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchelsea. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchelsea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchelsea holiday rentals we have selected for you start as low as €87 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchelsea rentals

At Expedia, we put the best Winchelsea holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchelsea rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchelsea holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchelsea. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winchelsea?

Yes, there are holiday rentals close to the most popular sights in Winchelsea, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

What are some of the best holiday rentals that Winchelsea has to offer?

Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters: This holiday home rental outside of Winchelsea offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winchelsea?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Winchelsea stay.

What’s there to see and do in Winchelsea?

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

What’s a holiday rental in Winchelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchelsea. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.