Chailey Vacations from $670

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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.
Hilton Woking

Hilton Woking

4 out of 5
Price was $750, price is now $670 per person
$670
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
9.4/10 Exceptional! (84 reviews)
Very enjoyable stay for a Christmas event. The food, waiter service and music/DJ were all excellent and the photography was an unexpected highlight for the evening. My only comment is the room could have been better decorated with Christmas decorations as the outer edges of the room were quite bland.

Reviewed on Dec 15, 2025

The New England

The New England

4 out of 5
Price was $1,019, price is now $873 per person
$873
per person
Mar 2 - Mar 7
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to London (LGW)
9.8/10 Exceptional! (106 reviews)
Very friendly staff. Bedroom and bathroom clean and comfortable. Breakfast choice very good and well cooked. Walking distance from town, pier and promenade.

Reviewed on Oct 14, 2025

Bloc Hotel London Gatwick Airport

Bloc Hotel London Gatwick Airport

3 out of 5
Price was $811, price is now $760 per person
$760
per person
Feb 13 - Feb 17
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LGW)
8.8/10 Excellent! (4,449 reviews)
The only thing I did not like was when having a shower, floor ended up soaking wet and it could cause an accident.

Reviewed on Dec 24, 2025

Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Price was $845, price is now $739 per person
$739
per person
Mar 15 - Mar 21
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,020, price is now $905 per person
$905
per person
Mar 15 - Mar 21
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to London (LGW)
9/10 Wonderful! (812 reviews)
Everything was clean and tidy, staff helpful and courteous, food pretty good (decent breakfast buffet and dinner menu). A little chilly in the room even with the temp set to 26 but otherwise extremely comfortable room.

Reviewed on Dec 16, 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 Glynde. Check out the shops and charming cafes in this walkable area.

Glyndebourne Opera House

Charleston Farmhouse

Find out about the history of Firle 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

SEA LIFE Brighton

SEA LIFE Brighton

$21
per adult
SEA LIFE Brighton
Brighton: Escape the Vault and Rob a Bank Escape Room

Brighton: Escape the Vault and Rob a Bank Escape Room

$32
per adult
100% of travellers recommend
Brighton: Escape the Vault and Rob a Bank Escape Room
Another view of The Seven Sisters, with our guide, Lawrence.

Seven Sisters & South Downs Tour with Train Tickets Included

$131
per adult
100% of travellers recommend
Seven Sisters & South Downs Tour with Train Tickets Included
See all activities in Chailey

Chailey Hotel Deals

Bloc Hotel London Gatwick Airport

Bloc Hotel London Gatwick Airport

3 out of 5
South Terminal, Gatwick Airport Gatwick England
$109 nightly
The price is $130 total per night from Jan 18 to Jan 19
$130 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
8.8/10 Excellent! (4,581 reviews)
All international airports should have a hotel like this situated inside near the terminals. It is very convenient.

Reviewed on Dec 22, 2025

Bloc Hotel London Gatwick Airport
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
$112 nightly
The price is $134 total per night from Jan 4 to Jan 5
$134 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (3,863 reviews)
Is not my first time I stayed in this hotel and as I expected the experience was amazing room clean and comfortable ideal if you have an early flight especially with kids I will use this hotel again

Reviewed on Dec 22, 2025

Hilton 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
$65 nightly
The price is $78 total per night from Jan 1 to Jan 2
$78 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.6/10 Excellent! (1,440 reviews)
Was clean but a little wear and tear. Comfortable and good value for money though.

Reviewed on Dec 17, 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 $670 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.