Winchelsea Vacations from $669

Book a Hotel + Flight or Car together to unlock savings

Photo by Snappy David

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Premier Inn Sunbury - Kempton Park

Premier Inn Sunbury - Kempton Park

3 out of 5
Price was $677, price is now $669 per person
$669
per person
Feb 28 - Mar 5
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to London (LGW)
8/10 Very Good! (2 reviews)
ORIDA Maidstone Hotel

ORIDA Maidstone Hotel

3 out of 5
Price was $821, price is now $701 per person
$701
per person
Mar 11 - Mar 16
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to London (LGW)
8.6/10 Excellent! (1,171 reviews)
Disappointed is the best I can say.Jacuzzi and steam room didn't work for 2 out the 4 days we stayed.Heater in the room didn't work on the last day and enquired 3 times .When I asked for a electric heater that was in the bar area I was told that I can come over to get it when they're close at 23:00.That was unacceptable to me and I don't think we're going to stay there again,bear in mind that we stayed 3 times over the years.

Reviewed on Jan 2, 2026

Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Price was $935, price is now $810 per person
$810
per person
Mar 13 - Mar 20
found 3 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
8/10 Very Good! (1,001 reviews)
It was ok for the price but I’ve been in travelodges that have more room amenities. No glasses, just mugs and a kettle. All the sockets are extremely low and so it’s either difficult to or you’re not able to get the plugs in you need that you’ve bought with you. In our room the air con came on in the middle of the night, and in our room it had a spanner showing that it had a problem…so I was unable to turn it off and it was pretty noisy so had about 1.5 hours of trying to get back to sleep. Not the worst but also not the best.

Reviewed on Dec 13, 2025

East Sussex National

East Sussex National

4 out of 5
Price was $832, price is now $753 per person
$753
per person
Feb 27 - Mar 3
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to London (LGW)
9/10 Wonderful! (812 reviews)
The rooms were very dusty and tiles in bathroom could do with some mould spray and a scrub. We had trouble getting robes and slippers sent to the room and then when they sent them they forgot slippers and 1 of the robes and we was nearly late for our treatment as was told to wait in our rooms for them. Reception team could have been more welcoming and smiley.

Reviewed on Jan 2, 2026

Market Garden Cottage

Market Garden Cottage

5 out of 5
Price was $1,129, price is now $1,118 per person
$1,118
per person
Feb 16 - Feb 20
just found
Roundtrip flight included
New York (JFK) to London (LGW)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Winchelsea
View all trips

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

After visiting Church of St Thomas a Becket, make a plan to see the other sights and activities in Icklesham. Check out the spas and top-notch restaurants in this relaxing area.

Church of St Thomas a Becket

Winchelsea Hotel Deals

The View Hotel

The View Hotel

3 out of 5
Grand Parade Eastbourne England
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $98 total per night from Jan 25 to Jan 26
$98 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
Great modern hotel, excellent value

Reviewed on Dec 30, 2025

The View Hotel
Hythe Imperial Hotel Spa & Golf

Hythe Imperial Hotel Spa & Golf

4 out of 5
Princes Parade Hythe England
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $85 total per night from Jan 25 to Jan 26
$85 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,083 reviews)
Great place to stay. Room excellent and comfortable, facilities everything you could need. Staff all very nice & courteous. All set in a great location.

Reviewed on Dec 30, 2025

Hythe Imperial Hotel Spa & Golf
Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Simone Weil Avenue Ashford England
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $108 total per night from Jan 18 to Jan 19
$108 total
Jan 18 - Jan 19
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
Clean room, good breakfast and bar meals

Reviewed on Dec 31, 2025

Ashford International Hotel & Spa
See all 1,961 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.

Find the Best Winchelsea Vacation Packages

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.

Winchelsea Essential Information

Language
English
Currency
British pounds sterling
Population
300
Max Temp Winter
45ºF
Max Temp Summer
65ºF
Top Sights
Camber Sands, Bodiam Castle and Winchelsea Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winchelsea vacation package cost?
You can pick up a vacation package to this popular destination from $669 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.