Winchelsea Holiday Rentals from €91: Search Short-Term Rentals

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

Large House, Contractors, Families, Free Parking : This holiday home rental outside of Winchelsea offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Holiday Rentals in Winchelsea

Relax in this serene space with a large bed, a sofa, and a small table.

"Warm welcome, comfortable and very clean apartment. Well stocked kitchen for a longer self catering stay. Well situated for town, beach, restaurants etc. loved the fresh fruit in reception and the tea and coffee available. "

Experience the vibrant urban atmosphere of this modern building, featuring a unique green wall and pedestrian-friendly design.

"The property has gone into administration "

Escape to a serene forest retreat with a cozy cabin surrounded by nature.

"The staff are so friendly and helpfull and we all enjoyed out stay."

includes taxes & fees

16 Jul - 17 Jul

Enjoy a serene ocean view from this seaside pavilion, featuring a dome roof and columns.

"Easy to find on Sat Nav, parking nearby, very light, warm and comfortable, bed a little hard for us oldies. Overall great. Thank you"

includes taxes & fees

21 Jul - 22 Jul

Perched above a serene moat, this historic castle offers breathtaking views of the surrounding landscape.

"Comfortable house, beautiful surroundings"

Enjoy cooking in this well-equipped kitchen with a microwave, stainless steel range hood, and ample glassware storage.

"I had a great stay with my wife, kid and dog. Beautifully furnished in antique furniture, modern kitchen and excellent balcony to enjoy a morning coffee in. Right in the middle of Old Town, you are a quick walk away from everything, really.We loved our stay."

Cozy space with a wood-burning stove, bench, and wicker basket. Enjoy a view of the outdoors from the large window.

"Beautiful views and great communication from the owner on how to find it and access your hut. We stayed in The Hive for one night and it was a little dusty, everything needed a deep clean. It didn’t ruin our trip, and would visit again in the hope this was a one off error."

includes taxes & fees

29 Jul - 30 Jul

Enjoy a tranquil beach experience with access to the calm sea.

Enjoy a serene beachside stroll along the promenade, surrounded by the soothing sounds of the ocean.

"Lovely accommodation. Relaxing stay. "

Explore the grandeur of this historic castle, featuring a central tower and a smaller tower, set amidst a beautifully manicured lawn and a paved pathway.

"The property lies right in the heart of a very cute town. Enjoyed our stay"

Experience glamping in a spacious pyramid-shaped tent with a comfortable bed and cozy bedding.

"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."

includes taxes & fees

15 Jul - 16 Jul

Enjoy a serene beach experience with access to the ocean and scenic views.

"Beautiful property in a perfect location. Second visit and looking forward to the third!"

Stroll along the beachfront promenade, offering scenic views of the sea.

"Just stayed one night, but great location by the beach with shops close by. Quite courtyard for evening drink."

Simple, residence surrounded by lush greenery and a small patio area.

"Always a great stay at Heron Cottage, this was our 5th stay so this must prove we love it!"

Relax in this serene bedroom with a large bed, two sofas, and a cozy rug.

Charming cottage with a steeply pitched roof, surrounded by lush greenery and a well-manicured lawn.

"Very relaxing and enjoyable visit. The sun shone and the views were fabulous. Would like to stay again."

Stunning interior with high ceiling, wooden floor, and a staircase leading to an upper level.

Cozy retreat with a bed, TV, kitchenette, and wardrobe.

"I needed immediate help when the sat sav dumped me nearby & my host talked me all the way to the front door which was a huge relief. The accommodation is dated but I knew that from the photos it was very clean though & i was surprised to find all the essentials had ben left. I wasn’t expecting that so had brought it all with me. The bed was very comfortable, the shower was lovely & the washing machine was handy. The area was very noisy though as it is right in town above a bar & I was there at...

Relax in this serene sunroom with a glass ceiling, overlooking a lush garden. Enjoy the curved sofa, wicker chairs, and a coffee table amidst a peaceful outdoor view.

"The property has everything for a very relaxing break. It's close enough for anything most people will want to enjoy. Plus it's location is very secluded and privacy is assured. I would recommend it to anyone."

includes taxes & fees

15 Jul - 16 Jul

Guests can enjoy breathtaking views of the expansive pebbly beach from a scenic ledge.

"nice property space for all the family ! weather beautiful ,so easy to walk along the beach."

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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 €91 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.

Recent reviews of Winchelsea properties

5/5 Excellent

"Room clean with safe and fridge. Happy to stay again. Good location to walk into town centre. "

A verified traveller stayed at Hampton by Hilton Ashford International

Posted 1 day ago

5/5 Excellent

"🌟 A Truly Majestic Experience in Eastbourne 🌟 From the moment I arrived at The Majestic Hotel, I felt genuinely welcomed. The elegant yet homely atmosphere set the tone for a wonderful stay, and every staff member exuded warmth and professionalism. 🏩 My newly refurbished room offered a breathtaking sea view—fresh, serene, and spotless. The hotel provides a range of beautifully presented rooms to suit all preferences. 🍽️ Mealtimes were a treat! Every dish was full of flavour, made with care, and served with genuine smiles. 🍸 The lounge and bar area are perfect for relaxing, and the patio out front is ideal for soaking in the sea breeze with a drink in hand. 🎶 Light entertainment on Wednesdays and Fridays adds to the magic—fun, lively, and utterly enjoyable. 💫 Special thanks to the lovely receptionist, the charming bartender, and the outstanding manager—the heartbeat of the hotel. 👨‍🍳 Tip: Ask about the beef lasagne—comforting, delicious, and reminiscent of my mum’s homemade version. 🙏 To the entire team: thank you for an unforgettable experience. I’ll definitely be back! 📣 Don’t wait—book now and experience the charm for yourself."

A verified traveller stayed at The Majestic Hotel

Posted 7 days ago

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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?

Large House, Contractors, Families, Free Parking: This holiday home rental outside of Winchelsea offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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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Holiday Rentals in Winchelsea

Osborne Apartments

Vive Hotel

Pinewood Camping Pods - At Port Lympne Reserve

Bexlet

A pretty 4* detached rural holiday cottage in the heart of the Kent countryside

Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.

Extraordinary Huts

Golden Tides Seaside Retreat in Saint Leonards

Humphries Cross Apartments

16th Century Cottage Situated Opposite The Medieval Landgate Arch

Oastbrook Glamping

Sandunes 2

Lovely beachfront Apartment with private courtyard

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

Tranquil Loft Apartment Overlooking Countryside

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

A tranquil farm stay in the Weald of Kent, 50mins from central London via PT.

Grace Apartments - Living Rock

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

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

Find out more about Winchelsea

Recent reviews of Winchelsea properties

Hampton by Hilton Ashford International

Hythe Imperial Hotel Spa & Golf

The Burlington Hotel

Holiday Inn Ashford North A20 by IHG

OYO Stade Court Hotel

The Cumberland Hotel

The Majestic Hotel

Eastbourne Riviera Hotel

Afton Hotel

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Frequently asked questions