Winchelsea Holiday Rentals

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Holiday Rentals in Winchelsea

Osborne Apartments

2.5 star property
Eastbourne
9.0 out of 10, Wonderful, (87)
"Great place to spend a few days, the room was excellent, spacious and clean and the staff were always happy to help with any questions as we had 2 children with us. Would happily stay here again, thanks Osbourne Apartments."
United Kingdom
Anonymous traveller
Osborne Apartments

Pinewood Camping Pods - At Port Lympne Reserve

2.0 star property
Hythe
9.4 out of 10, Exceptional, (29)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is NZ$334
includes taxes & fees
24 Nov - 25 Nov
Pinewood Camping Pods - At Port Lympne Reserve

Extraordinary Huts

3.0 star property
Rye
9.6 out of 10, Exceptional, (40)
"We wanted quiet, peaceful, beautiful, unique and considerate and that’s what we got. To be woken up by pheasants and lambs, dinner at The Plough, logs being burnt inside and out and amazing views and walks… it was all there."
United Kingdom
Casey
Extraordinary Huts

Big2vacation2 Exclusive at new Beach Caravan Park

3.0 star property
Romney Marsh
The price is NZ$492
includes taxes & fees
25 Nov - 26 Nov
Big2vacation2 Exclusive at new Beach Caravan Park

1-bedroom Apartment Sleeps 4, Parking

3.0 star property
Hythe
10.0 out of 10, Exceptional, (1)
The price is NZ$302
includes taxes & fees
26 Nov - 27 Nov
1-bedroom Apartment Sleeps 4, Parking

Bexlet

2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (50)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is NZ$177
includes taxes & fees
1 Dec - 2 Dec
Bexlet

Big2vacation Exclusive Camber Sands Holiday Park

3.0 star property
Rye
The price is NZ$492
includes taxes & fees
7 Dec - 8 Dec
Big2vacation Exclusive Camber Sands Holiday Park

Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters

Hastings
"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 NZ$671
includes taxes & fees
26 Nov - 27 Nov
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters

2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.

Hythe
10.0 out of 10, Exceptional, (17)
"Had a wonderful stay would recommend to anyone"
United Kingdom
Susan M.
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Bexhill
10.0 out of 10, Exceptional, (6)
"Perfect location. Perfectly comfortable."
United Kingdom
alex
The price is NZ$268
includes taxes & fees
24 Nov - 25 Nov
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Gun Hill Cottage

3.5 star property
Heathfield
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 NZ$1,716
includes taxes & fees
27 Nov - 28 Nov
Gun Hill Cottage

Character Beamed Country Retreat with self check in/out in historic 1066 country

Broad Oak
9.8 out of 10, Exceptional, (213)
"We had a wonderful stay in a nice place. Everything we needed was there. "
Netherlands
Petra v.
Character Beamed Country Retreat with self check in/out in historic 1066 country

Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Hellingly /Hailsham
7.6 out of 10, Good, (9)
"The property was incredible and the host had incredible communication. Maria could not have been more accommodating and we cannot thank her enough, we had a fabulous stay and hope to be back soon."
United Kingdom
Matilda B.
The price is NZ$1,175
includes taxes & fees
24 Nov - 25 Nov
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Extra-large luxury Shepherd's Hut, private hot tub, Smart TV, wifi, fab views.

Herstmonceux
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.

Coastguard Cottage With Sea Views

fairlight
9.8 out of 10, Exceptional, (80)
"It was lovely, such a nice place to stay and an awesome view. "
Netherlands
Mildred v.
Coastguard Cottage With Sea Views

Outstanding luxury beachfront holiday experience with hot tub

Pevensey Bay
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

Tranquil Loft Apartment Overlooking Countryside

3.0 star property
Hailsham
10.0 out of 10, Exceptional, (1)
Tranquil Loft Apartment Overlooking Countryside

Stunning Spacious Seaside cottage, 1 minute from the beach sleeps 12

Camber
9.6 out of 10, Exceptional, (47)
"Ideally situated for the beach, parking for 3 vehicles, spacious downstairs. "
United Kingdom
Martin H.
Stunning Spacious Seaside cottage, 1 minute from the beach sleeps 12

Cozy Camber Caravan 3 Bedroom Retreat With Decking

3.0 star property
Rye
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 NZ$392
includes taxes & fees
25 Nov - 26 Nov
Cozy Camber Caravan 3 Bedroom Retreat With Decking

The Boathouse

3.0 star property
St Leonards-On-Sea
10.0 out of 10, Exceptional, (1)
The price is NZ$948
includes taxes & fees
7 Dec - 8 Dec
The Boathouse
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

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, 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 NZ$177 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 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 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.