Winchelsea Holidays

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Top hotels in Winchelsea

Winchelsea Lodge

Winchelsea Lodge

3 out of 5
Hastings Road, Winchelsea, England
The price is 3.875.269 ₫ per night from 10 Sept to 11 Sept
3.875.269 ₫
3.875.269 ₫ total
10 Sept - 11 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 4.110.133 ₫ per night from 17 Aug to 18 Aug
4.110.133 ₫
4.932.160 ₫ total
17 Aug - 18 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 2.378.006 ₫ per night from 7 Sept to 8 Sept
2.378.006 ₫
2.853.607 ₫ total
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.

Popular places to visit

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

How much does a Winchelsea holiday package cost?
You can pick up a holiday package to this popular destination 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.