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Holiday Rentals in Winchelsea

"Very pleased with the accommodation, had never been to winchelsea before but loved where the house was. Proper old building with creaky floors and doors which we loved. The host had left a basket of lovely goodies for us and there was everything we needed. Great garden to sit in too. "

"Lovely clean room.The mattress is a little thin and can feel the springs so didn’t sleep too well. Within walking distance to shops and pier. "

includes taxes & fees

24 Feb - 25 Feb

"We booked Mary's wonderful house for a weekend away in December for a catch up with old friends (12 of us in total). We had an amazing time and really recommend the house. It has lots of character from being an old pub called The Star and the rooms were really comfy with almost all of them having their own ensuite bathroom. The kitchen is well equipped and spacious for cooking even for 12 people and we loved the fireplace and piano in the main living room. We didn't get out much due to storms...

"The pod was Cody and warm. We loved being so close to the lions and hearing them roar ! My family and I loved the whole adventure ! "

includes taxes & fees

3 Feb - 4 Feb

"The apartments are lovely, and have everything you need; washing machine, microwave, toaster, oven etc. The only thing that would stop me coming again, is the exorbitant price charged for dogs. £20 per dog PER NIGHT! We have 2 small dogs, staying for 5 nights which would be an extra £200 on the bill! We queried it, and they reduced it to £15 per dog per night. But that is still an extra £150. Other places we have stayed in, charge between £20-£50 per stay. So, as lovely and convenient as it is,...

includes taxes & fees

6 Feb - 7 Feb

"Brilliant location for mixed aged family group, kids and parents loved the beach.Plenty of rooms and space for the kids to play and older family member to find quiet space. "

"The house was great for our party of 2 families. We had plenty of space and the house is very well equipped. A lovely clean house and great communication with the host. We enjoyed exploring the local area and the house was located well for this. The driveway down had lots of bumps and pot holes which you need to be careful of especially in the dark but other than this wouldn’t change a thing."

"A lovely little cottage retaining many original features. A well set out kitchen, given the space constraints, and a clean, well maintained bathroom. Comfy for 2 adults, with the furniture, log burner and exposed beams making the sitting room very cosy. The stairs are (very) steep, and the property would not be suitable for anyone with mobility issues, but that is flagged in the description. Very central location for Rye, and easy parking in the cattle market car park. There is also short...

"Overall good with one caveat and a slight disappointment. The house was very comfortable to live in for a week, very well equipped, lovely lounge, comfortable kitchen, conservatory and outside space for all the family. The one issue for us were the quality of the mattresses. The upstairs main bedroom was way too soft,and the downstairs front bed also too soft. The other issue, not to do with the property was there was a warning on the beach not to go into the water because of poor water...

"Very responsive property manager who really went the extra mile (thank you)! A beautiful house full of character."

"Can’t recommend this place enough. We had a fantastic stay here for New Year’s Eve. The photos don’t do the place justice - it has so much space, and so much character. The location is unbeatable on the iconic Mermaid Street, 5 minutes from the station. Easy check in process. Would so recommend for a large group looking for a stay in Rye. "

Fridge, microwave, oven, electric kettle

"Everything it says in the description, clean & tidy, excellent area, peace and quiet. Had a lovely relaxing break, dogs loved it. Although the fidge needs looking at, but didn't spoil the moment."

"The location of sandunes 2 is perfect, right on the beach. The accommodation was very well equipped, especially the kitchen. The kids loved exploring the sandunes"

3 bedrooms, iron/ironing board, travel cot, WiFi

"Well located, thoughtfully renovated and very comfortable. Ideal if you have a dog "

"The property was very clean and tidy. Everything was excellent about the property. Looked out of the French doors on Christmas Eve and the field it looks out on had a herd of reindeer’s running around in it , how festive. Will book this property again, Many Thanks , Wendy& Peter"

"This was our third time at the Stables and we just love it. Its so clean, cosy and comfortable. We love that its just in the middle of the countryside on the edge of beautiful woodland. Nick and Janet are super hosts."

"Tim came to the rescue! We had been planning my daughters Hen celebrations since last October. Everything going to plan until ......... The accommodation we had originally booked had to be cancelled on the day we were due to depart due to no water in the area! Panic! Until we found Tim's property. He was so calm and responded really quickly to my messages. Organised the booking in 4 hours and sent all information over so quickly. The property is stunning pictures don't do it justice . Kitchen is...

"The sunrooms were amazing fantastic view of the beautiful beach. Property was well kitted out, very comfortable and a really good location. It was a good property for my 89 year old mother as she was able to sleep downstairs. The Owl was excellent."

"Property was lovely & comfortable.well equipped.Nice and clean.host was lovely and couldnt do enough but left us to enyoy the break.was at hand if needed.Perfect for the dogs.would recommend and stay again"

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"Lovely quiet stay, the staff couldn’t be more friendly and helpful. Great breakfasts. "

includes taxes & fees

3 Feb - 4 Feb

"Very pleased with the accommodation, had never been to winchelsea before but loved where the house was. Proper old building with creaky floors and doors which we loved. The host had left a basket of lovely goodies for us and there was everything we needed. Great garden to sit in too. "

"Lovely room and great food. What let it down was the run down main bar area downstairs and also the spa wasn't working properly and we were unable to use some of the facilities. "

includes taxes & fees

6 Feb - 7 Feb

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 €89 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.

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All accommodation types in Winchelsea

Cottages in Winchelsea

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?

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly: 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 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Winchelsea?

With 6 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 Church of St Thomas a Becket 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.

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Holiday Rentals in Winchelsea

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Check prices for these dates

Holiday Rentals in Winchelsea

Close to the beach and to historic Rye - delightful 3 bed Cottage & garden

Vive Hotel

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly

Pinewood Camping Pods - At Port Lympne Reserve

Osborne Apartments

Family & Pet Friendly Home Direct On A Lovely Sandy Beach

Secluded Farmhouse set in 300 acres, sleeps 11 comfortably, and up to 14 people.

Stunning 6 Bedroom Farmhouse in Hellingly

16th Century Cottage Situated Opposite The Medieval Landgate Arch

Entire Beach House, beautiful sea views & direct beach access on the Kent coast

Our charming & comfortable old Manor house sleeps up to 20, with Jacuzzi & Pool.

Superb medieval house with spacious private garden in the centre of Rye

Lillibelles lake house

Sandunes 2

Coastguard Cottage With Sea Views

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

Converted stable in secluded rural setting.

Seven bedroom country house with expansive garden & hot tub

Beach Front Cottage with Direct Access to Stunning Sandy Beach, Dunes & Sea View

Beautiful Countryside cottage

Other types of properties in Winchelsea you may be interested in

Winchelsea Lodge

Close to the beach and to historic Rye - delightful 3 bed Cottage & garden

Hythe Imperial Hotel Spa & Golf

Find out more about Winchelsea

Explore a world of travel with Expedia

Frequently asked questions