Winchelsea Holidays from £156

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Your Winchelsea Holiday

Select a Winchelsea holiday package and concentrate on what's important — enjoying yourself. There's no more planning stresses, just a lot more free time to uncover the charms of this fascinating city, such as its rich history and coastal scenery. Camber Sands, Rye Harbour Nature Reserve and Pett Level Beach are just a few of the attractions you'll want to check out during your trip to Winchelsea. Expedia has what you need to escape your routine. Tailor your holiday to Winchelsea to suit your travel style, whatever that may be.

Top Winchelsea Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sandman Signature London Gatwick Hotel

Sandman Signature London Gatwick Hotel

4 out of 5
per person
3 Oct - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to London (LGW)
8.6/10 Excellent! (1,003 reviews)
No water or lotion in the room. Front desk a bit unpleasant in the am. Bought water from front desk...

Reviewed on 10 Aug 2025

Bloc Hotel London Gatwick Airport

Bloc Hotel London Gatwick Airport

3 out of 5
per person
3 Oct - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to London (LGW)
9/10 Wonderful! (4,324 reviews)
Very comfortable and quiet nights sleep ahead of flight next morning. Stayed in room until 1 hr before departure. Only hiccup was the tv stopped working but this was just before check out. Would like to see usb ports for charging mobile as I don’t carry a plug

Reviewed on 12 Aug 2025

Winchelsea Beach Holiday

Listen to the soothing sound of waves rolling into the shore and stroll by the sparkling waters during your Winchelsea holiday. If you're craving some time out, a trip to Winchelsea will work wonders. We have plenty of Winchelsea holiday packages to choose from. Snap one up close to Winchelsea Beach, just 2 miles from the city centre, and live out your holiday dreams without blowing your budget.

Winchelsea Essential Information

Language
English
Currency
British pounds sterling
Population
300
Max Temp Winter
7ºC
Max Temp Summer
18ºC
Top Sights
Camber Sands, Winchelsea Beach and Carr Taylor Vineyard

Top hotels in Winchelsea

Winchelsea Lodge

Winchelsea Lodge

3 out of 5
Hastings Road, Winchelsea, England
The price is £106 per night from 12 Sept to 13 Sept
£106
12 Sept - 13 Sept
includes taxes & fees
8.4/10 Very Good! (317 reviews)
"A beautiful property with quaint gardens within the grounds. Room was for four of us, we had a double bed and a bunk. It was a small room but perfect for us. Bright, airy, and clean with an ensuite shower. Breakfast was included and was a great selection of hot, fresh fruit, cereals with coffee and ..."

Reviewed on 4 Aug 2025

Winchelsea Lodge
The New Inn

The New Inn

4 out of 5
German Street, Winchelsea, England
The price is £130 per night from 25 Aug to 26 Aug
£130
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (146 reviews)
"A really lovely place to stay, a perfect quiet and very pretty little village. The pub owners and bar staff were very welcoming and made a wonderful breakfast, and we had dinner there one night too which was fab!"

Reviewed on 3 Aug 2025

The New Inn
Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Simone Weil Avenue, Ashford, England
Fully refundableReserve now, pay when you stay
The price is £81 per night from 7 Sept to 8 Sept
£81
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"I’ve got to say the service was 10/10 and I think it was the assistant manager who went above and beyond to make sure everyone was happy and got everything they needed, will definitely be going back"

Reviewed on 9 Aug 2025

Ashford International Hotel & Spa
See all 2,098 properties in Winchelsea
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.

The Advantages of Winchelsea Weekend Breaks

Discover a different side of the British Isles with a weekend break in Winchelsea. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Winchelsea weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Winchelsea.

Cheap Weekend Breaks to Winchelsea

There are lots of ways to take cheap weekend breaks to Winchelsea. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Winchelsea. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Winchelsea Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Winchelsea. Whisking your lover away for a romantic Winchelsea weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Winchelsea and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire.

Family Weekend Breaks in Winchelsea

Set some time aside to experience family weekend breaks in Winchelsea. There are plenty of excellent family-friendly hotels in Winchelsea within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Winchelsea. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Winchelsea family weekend breaks.

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Winchelsea Beach

Winchelsea Beach

Why not spend a care-free afternoon at Winchelsea Beach during your travels in Icklesham?

Winchelsea Beach

St. Thomas the Martyr

Find out about the history of Icklesham with a stop at St. Thomas the Martyr. Wander through the seaside and beautiful beaches in this relaxing area.

St. Thomas the Martyr

Church of St Thomas a Becket

Find out about the history of Icklesham with a stop at Church of St Thomas a Becket. Wander through the seaside and beautiful beaches in this relaxing area.

Church of St Thomas a Becket

Frequently asked questions

Why should I book my Winchelsea holiday with Expedia?
With top-value airfares, car hire and accommodation choices all in one convenient place, Expedia makes booking your Winchelsea adventure hassle-free. Moreover, we can help you bundle your bookings into a package holiday so you can save even more. Pick from amazing escapes, add your flights and/or a car hire (and maybe also some fun tours!) and get unbeatable prices. Need to change your plans? Expedia offers a flexible cancellation policy for many bookings. To learn more, make your way to our Customer Service Portal link.
When is the best time of year to holiday in Winchelsea?
If you're eager to experience the buzz of Winchelsea during the high season, lock in your adventure for March, April and July. September, November and December are usually the quietest months of the year. With daytime average temperatures of 5ºC, January is the coolest period in Winchelsea. The warmest time of year is July, when you can experience average temperatures of 17ºC during the day. Whatever the weather conditions, you'll discover a whole lot to keep you occupied here.
What are the top hotels for my holiday in Winchelsea?
If you're hoping to stay close to Winchelsea, reserve a room at Church Cottage or Close to the beach and to historic Rye - delightful 3 bed Cottage & garden. Both will make you feel at home and are favourites among lots of travellers.
How do I get a cheap holiday to Winchelsea?
If you love getting a great deal, combine your bookings into a Winchelsea holiday. Whether you're looking for hotels, flights, hire cars or tours, you can book everything in one place. You'll have plenty of choice at your fingertips too. Expedia has over 400 air carriers and 321,000 properties worldwide to take your pick of. Fly with who you prefer, stay in a place you like and save precious pounds — now that's the perfect escape! Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Winchelsea holiday?
Ensure your holiday in Winchelsea is one to remember by visiting its best attractions. Bodiam Castle, Blue Reef Aquarium, Camber Sands and Great Dixter House and Gardens are a few of the things you must see while you're in the city.
What is the best area to stay in when on holiday in Winchelsea?
If you'll be visiting Winchelsea Beach, maximise your time sightseeing and book a stay close by. It's one of the best attractions in Winchelsea.
Do I need a visa for my Winchelsea holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the purpose of your visit, whether it be for work or pleasure, will determine if you need a visa for Winchelsea. Also be sure that your passport is up to date and has a minimum of six months validity remaining beyond your return date. Do all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Winchelsea holiday?
Though everyone's style is different, it can be useful to have a few guidelines for what to wear during your holiday in Winchelsea. We recommend browsing social media before you head off to get inspiration for local fashion trends.
What does an Expedia Winchelsea holiday include?
That depends on what type of getaway you want to have. Winchelsea travel deals can include hotels, flights and car hires. You can mix and match to create the travel package that suits your needs. You can also add on activities and experiences after you've booked to get even bigger discounts. Expedia has a wide selection of properties in Winchelsea, providing you with the freedom to tailor-make your escape. Apartments and cottages are some of the most popular stays for visitors here.
Does Expedia offer Book Now, Pay Later Winchelsea holidays?
We certainly do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in manageable instalments. Simply select the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: If paying across multiple transactions is what works best for you, Klarna offers just that! Paying in multiple instalments will make that dream getaway possible.
  • No-deposit holidays: When you see an incredible deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Winchelsea Expedia holiday?
Expedia has access to more than 400 partner airlines worldwide, so you definitely can. Just pick the carrier you want and create the perfect Winchelsea trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.