Winchelsea Vacations from $724

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Your Winchelsea Vacation

Select a Winchelsea vacation 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 vacation to Winchelsea to suit your travel style, whatever that may be.

The Latest Winchelsea vacation packages

Price found within the past 48 hours. Click for updated prices.
OYO The Watermans Arms Hersham

OYO The Watermans Arms Hersham

3.5 out of 5
Hersham
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LGW)
7.2/10 Good! (5 reviews)
Spring River Ebbsfleet by Marston's Inns

Spring River Ebbsfleet by Marston's Inns

3 out of 5
per person
Oct 1 - Oct 8
found 24 hours ago
Roundtrip flight included
New York (JFK) to London (LGW)
9/10 Wonderful! (1,000 reviews)
The room was nice and comfy enough for my family and I.

Reviewed on Aug 13, 2025

Foley Hotel

Foley Hotel

3.5 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LGW)
9.6/10 Exceptional! (198 reviews)
Lovely hotel and pub. Room was impressive, nice and large, and spotlessly clean Super king bed was unexpected. Rarely seen in many hotels so this was a definite delight. Only downside to the pub as a guest was we were unable to get a nightcap on our return at 11pm. Breakfast very nicely set out. Ingredients fresh and flavoursome. If returning to the are, will definitely stay again.

Reviewed on Aug 5, 2025

The Flower Pot

The Flower Pot

4 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LGW)
8.4/10 Very Good! (295 reviews)
Such a beautiful place! The room was just stunning and very clean. Very spacious with big bathroom and free standing bath which added a nice touch. The staff were so lovely and helpful and the food was very good although my pizza was slightly more done than I would have liked but still enjoyable. 30 seconds walk and there is a lovely place to walk down the river and watch the boats. Lovely outdoor seating area to enjoy some food and a drink. Would definitely stay here again.

Reviewed on Jun 26, 2025

Savannah Bed & Breakfast

Savannah Bed & Breakfast

4 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LGW)
9.8/10 Exceptional! (41 reviews)
Easy to find.....the owner very helpful and friendly. Room very clean and the breakfast was lovely.

Reviewed on Jul 7, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winchelsea
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Discover the most popular places to visit in Winchelsea

Beautiful bike ride at sunrise

Winchelsea Beach

Why not spend a carefree 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 the seaside and beautiful beaches in this relaxing area.

Church of St Thomas a Becket

Winchelsea Hotel Deals

Winchelsea Lodge

Winchelsea Lodge

3 out of 5
Hastings Road, Winchelsea, England
$149 nightly
The price is $149 total per night from Sep 10 to Sep 11
$149 total
Sep 10 - Sep 11
Total includes taxes and fees
8.4/10 Very Good! (319 reviews)
"Property was very clean .. crisp white bed linen.. rooms a bit outdated but good value for money in August .. lovely breakfast, lovely fresh fruits"

Reviewed on Aug 10, 2025

Winchelsea Lodge
The New Inn

The New Inn

4 out of 5
German Street, Winchelsea, England
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $189 total per night from Aug 31 to Sep 1
$189 total
Aug 31 - Sep 1
Total includes taxes and 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 Aug 3, 2025

The New Inn
The Burlington Hotel

The Burlington Hotel

3 out of 5
Grand Parade, Eastbourne, England
Fully refundableReserve now, pay when you stay
$55 nightly
The price is $66 total per night from Aug 31 to Sep 1
$66 total
Aug 31 - Sep 1
Total includes taxes and fees
7.6/10 Good! (1,290 reviews)
"Spacious room with nice sized TV. Big comfortable hotel."

Reviewed on Aug 13, 2025

The Burlington Hotel
See all 1,993 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.

Winchelsea Beach Vacation

Get set to live out those summer daydreams on your upcoming Winchelsea vacation. Head off on a lovely stroll, admire the sparkling coastal views and pick up unique seashells on your trip to Winchelsea. Located just 1 mile from the town center, 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 vacation in Winchelsea. Why not check out some apartments, like Winchelsea Lodge and Strand House? They're a hit with travelers 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 vacation deals, you'll have more money in your back pocket to explore.

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Frequently asked questions

How much does a Winchelsea vacation package cost?
You can pick up a vacation package to this popular destination from $724 on Expedia. However, how much your vacation 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?
September, November and December are the best times to look for cheap Winchelsea vacation packages. Choosing to travel in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Winchelsea?
To fully enjoy your Winchelsea vacation, we suggest staying for 2 days. Split your time between visiting St. Thomas the Martyr, Church of St Thomas a Becket and other major sights, as well as exploring neighborhoods like Icklesham and Playden. If you've got some spare time, add a day trip or tour to your Winchelsea vacation itinerary.
Is it worth booking a vacation package to Winchelsea?
Popular for its views, walking trails and nature, a Winchelsea vacation offers something for everyone. Be sure to check out key sights like Winchelsea Beach and Camber Castle, and consider renting a car for day trips to discover even more.
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 vacation package as soon as possible.
Is it cheaper to book a Winchelsea vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights individually. Better still, you can personalize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Winchelsea vacation packages?
Your Winchelsea break should be a relaxing escape from your daily routine, not a reason for money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.