Winchelsea Holidays

Photo by Snappy David

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Top Flight + Hotel Deals in Winchelsea

Price found within the past 48 hours. Click for updated prices.
Hampton by Hilton London Gatwick Airport

Hampton by Hilton London Gatwick Airport

3.5 out of 5
per person
17 Oct - 19 Oct
found 2 hours ago
Return flight included
Dublin (DUB) to London (LGW)
8.8/10 Excellent! (1,967 reviews)
Great for early Easy Jet flight!

Reviewed on 4 Aug 2025

Winchelsea Beach Holiday

Get set to live out those summer daydreams on your upcoming Winchelsea holiday. Head off on a lovely stroll, admire the sparkling coastal views and pick up unique seashells on your trip to Winchelsea. Located just 2 kilometres from the town centre, Winchelsea Beach is the place to be for many visitors. Browse our Winchelsea packages and watch your travel budget stretch further!

Things You Should Know About Winchelsea

  • Doze off to the gentle sounds of the sea in one of our Winchelsea beach hotels. There's nothing quite like staying right by the water.
  • Whatever your tastes or budget, you'll find a great place to stay for your holiday in Winchelsea. Why not check out some apartments, like Winchelsea Lodge and Strand House? They're a hit with travellers of all sorts.
  • Winchelsea is home to 300 people and offers plenty to keep you busy. Ready to start planning some exciting activities? Head straight to our Winchelsea things to do page for some inspiration.
  • Winchelsea Beach, Winchelsea Beach and Church of St Thomas a Becket are just some of the attractions that should be on your sightseeing list. With our Winchelsea holiday deals, you'll have more money in your back pocket to explore.

Top hotels in Winchelsea

Winchelsea Lodge

Winchelsea Lodge

3 out of 5
Hastings Road, Winchelsea, England
The price is €138 per night from 21 Aug to 22 Aug
€138
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (313 reviews)
Good for a short stay
"All in all, the hotel is okay. It's getting a bit long in the tooth, and I would describe the facilities as rather basic overall. Room service is only provided when required. Breakfast is okay."

Reviewed on 3 Aug 2025

Winchelsea Lodge
The New Inn

The New Inn

4 out of 5
German Street, Winchelsea, England
The price is €161 per night from 7 Aug to 8 Aug
€161
7 Aug - 8 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 €97 per night from 6 Sept to 7 Sept
€97
6 Sept - 7 Sept
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Paid a good price for room.It was clean smelt fresh and was a good size i wish they would put apps like Netflix on the TV's in the rooms as no entertainment other than pool table in bar area.Breakfast was great set out well, fresh fruit, pastries hot cooked breakfasts etc was pleasantly surprised..Would ..."

Reviewed on 1 Aug 2025

Ashford International Hotel & Spa
See all 2,109 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.

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

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

How much does a Winchelsea holiday package cost?
You can pick up a holiday package to this popular destination from €253 on Expedia. However, how much your holiday to Winchelsea costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Winchelsea?
To score cheap Winchelsea holiday packages, organise your getaway outside of peak periods such as school holidays. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Winchelsea?
With about 2 days, you'll have enough time to experience popular neighbourhoods like Icklesham and Playden during your Winchelsea holiday. Be sure to also add St. Thomas the Martyr and Church of St Thomas a Becket to your must-do list. Up for some more adventures? Consider venturing outside of Winchelsea on day trips and tours.
Is it worth booking a holiday package to Winchelsea?
Winchelsea has all the ingredients you need for an awesome break — nature, views and walking trails are just the start. Whether you want to check out attractions like Winchelsea Beach and St. Thomas the Martyr, or take the path less traveled, there's plenty to see and do on your Winchelsea holiday.
How to find the best Winchelsea package deals?
Use Expedia's filters to find some of the best Winchelsea package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Winchelsea package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Winchelsea holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking hotels and flights individually. Better still, you can personalise your Winchelsea trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Winchelsea?
Land incredible discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Winchelsea getaway.
How to plan a trip to Winchelsea?

  1. Pick your dates: The things you plan to do in Winchelsea and your preferred season can help you decide when to go.
  2. Set your budget: Consider costs like food, flights and transportation when calculating how much to set aside for your trip to Winchelsea. Then, choose a property that works with your budget, whether that's an affordable stay or a deluxe retreat.
  3. Decide how long to go away for: Now that you know more about Winchelsea, you can work out the right length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, book the right Winchelsea holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.