Chailey Vacations from $701

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Your Chailey Vacation

When a city adventure is calling your name, answer it with a Chailey vacation package. With all your travel needs taken care of before you leave, all you have to do here is concentrate on making unforgettable memories. Like to explore your new surroundings? Plumpton Racecourse, Lewes Castle and Barbican House Museum are three of the best places to visit during a trip to Chailey. Whoever you're taking time off with and whatever your budget, your dream Chailey vacation is just a few clicks away with Expedia.

The Latest Chailey vacation packages

Price found within the past 48 hours. Click for updated prices.
The View Hotel

The View Hotel

3 out of 5
Price was $831, price is now $701 per person
$701
per person
Jan 8 - Jan 14
found 9 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9.2/10 Wonderful! (1,010 reviews)
Whilst the room decor was adequate.. The window had a seal problem, that produced a continuous whistle when windy. Also the mechanics to the room was extremely noisy...Thefore did not have did not get mutch sleep.

Reviewed on Oct 26, 2025

Sofitel London Gatwick

Sofitel London Gatwick

4 out of 5
Price was $1,099, price is now $851 per person
$851
per person
Jan 8 - Jan 14
found 9 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9/10 Wonderful! (1,924 reviews)
Excellent hotel to stay in to start your holiday - ensuring stress free travel for an early morning flight

Reviewed on Oct 29, 2025

Beaverbrook

Beaverbrook

5 out of 5
Save 100% on your flight
Price was $2,664, price is now $2,168 per person
$2,168
per person
Jan 8 - Jan 14
found 9 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9.6/10 Exceptional! (31 reviews)
Beaverbrook is beautiful. But service (despite plenty of staff) is simply too inconsistent/ poorly trained for the price. Examples include a waitress in the deli being harsh with our 4 year old for sitting in her knees to reach the table, being told to wait 2 minutes for our table but being forgotten for 20 minutes, a room which was much too hot (an resulted in an uncomfortable night) despite having asked for it to be turned down (and told that it had) and promises of things being sorted which weren’t. All left a slightly sour taste.

Reviewed on Oct 29, 2025

Buxted Park Hotel

Buxted Park Hotel

4 out of 5
Price was $1,223, price is now $1,021 per person
$1,021
per person
Jan 8 - Jan 14
found 9 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9/10 Wonderful! (359 reviews)
The staff (Jamie) were great. The library room was a lovely room for our celebration

Reviewed on Sep 17, 2025

Hotel Continental

Hotel Continental

3 out of 5
Price was $933, price is now $811 per person
$811
per person
Jan 8 - Jan 14
found 9 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9/10 Wonderful! (385 reviews)
Clean room, friendly staff. Good full English breakfast. Nice location. Nice off street parking if you get their early enough

Reviewed on Oct 8, 2025

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Discover the most popular places to visit in Chailey

Lewes Castle

Lewes Castle

Learn about the local history of Lewes when you take a trip to Lewes Castle. Wander the seaside and beautiful beaches in this culturally rich area.

Lewes Castle

Glyndebourne Opera House

You can enjoy a show at Glyndebourne Opera House on your trip to Lewes. Check out the shops and lively bars in this walkable area.

Glyndebourne Opera House

Charleston Farmhouse

Find out about the history of Lewes with a stop at Charleston Farmhouse. Wander the area's seaside or simply enjoy one of its lively bars.

Charleston Farmhouse

What to do in Chailey

Another view of The Seven Sisters, with our guide, Lawrence.

Seven Sisters & South Downs Tour with Train Tickets Included

$146
per adult
100% of travellers recommend
Seven Sisters & South Downs Tour with Train Tickets Included
SEA LIFE Brighton

SEA LIFE Brighton

$22
per adult
SEA LIFE Brighton
From Brighton: Oxford, Windsor and Eton Full Day Trip

From Brighton: Oxford, Windsor and Eton Full Day Trip

$93
per adult
From Brighton: Oxford, Windsor and Eton Full Day Trip
See all activities in Chailey

Chailey Hotel Deals

Hilton London Gatwick Airport

Hilton London Gatwick Airport

4 out of 5
South Terminal Gatwick Airport, Gatwick, England
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $151 total per night from Nov 8 to Nov 9
$151 total
Nov 8 - Nov 9
Total with taxes and fees
8.8/10 Excellent! (3,633 reviews)
The location is perfect for the airport.

Reviewed on Oct 27, 2025

Hilton London Gatwick Airport
Bloc Hotel London Gatwick Airport

Bloc Hotel London Gatwick Airport

3 out of 5
South Terminal, Gatwick Airport, Gatwick, England
$104 nightly
The price is $124 total per night from Nov 18 to Nov 19
$124 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (4,483 reviews)
Great place to stay for an early flight.

Reviewed on Oct 28, 2025

Bloc Hotel London Gatwick Airport
Leonardo Hotel Brighton

Leonardo Hotel Brighton

4 out of 5
101 Stroudley Road, Brighton, England
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $84 total per night from Nov 9 to Nov 10
$84 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (1,381 reviews)
Very nice hotel right beside the station. Quiet and clean with comfortable bed and everything we needed.

Reviewed on Oct 27, 2025

Leonardo Hotel Brighton
See all 3,339 properties in Chailey
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 Chailey Vacation Packages

Chailey Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Gatwick Airport (LGW)
Top Sights
Lewes Castle, Barbican House Museum and Glyndebourne Opera House

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Frequently asked questions

How much does a Chailey vacation package cost?
You'll find cheap prices from $701 on Expedia for your Chailey break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chailey costs.
What are the cheapest months to go to Chailey?
If you're hoping to snag a cheap Chailey vacation package, consider traveling in June, August and December. You'll generally find better rates on accommodations and flights during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Chailey?
The ideal duration of your Chailey vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to check out all the leading attractions and explore some hidden treasures along the way.
How to find the best Chailey package deals?
Begin your search for a Chailey package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chailey package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chailey adventure off to a flying start.
Is it cheaper to book a Chailey vacation as a package?
You can enjoy significant savings on your next Chailey getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chailey?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Chailey trip.
How to plan a trip to Chailey?

  1. Choose when to travel: Check your schedule and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Chailey.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Chailey.
  3. Organize your Chailey getaway with Expedia's trip planning tool: Search for and book accommodations and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Chailey together.
  4. Work out your trip length: Consider how long you'd like to spend exploring Chailey. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Chailey vacation package.
  6. Book any excursions or activities: Here's the fun part — organizing everything you want to do and see. Explore some of the exciting things to do in Chailey and book your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Chailey vacation packages?
Your Chailey getaway is meant to be an escape from your daily routine, not a source of money-related stress. So to allow 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 split up the cost over 3, 6 or 12 months. Plus, there are no 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.