Chailey Vacations from $746

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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
per person
Oct 1 - Oct 5
found 19 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9.4/10 Exceptional! (35 reviews)
Wish there are laundry facilities on site

Reviewed on Aug 1, 2025

Oldlands Farm

Oldlands Farm

3 out of 5
per person
Sep 15 - Sep 21
found 22 hours ago
Roundtrip flight included
New York (JFK) to London (LGW)
9/10 Wonderful! (175 reviews)
Great location for the airport

Reviewed on May 29, 2025

Hilton London Gatwick Airport

Hilton London Gatwick Airport

4 out of 5
per person
Oct 1 - Oct 5
found 19 hours ago
Roundtrip flight included
New York (NYC) to London (LGW)
9/10 Wonderful! (3,030 reviews)
Very nice hotel and proximity to South Terminal excellent - we had early flight (5:25) so had to be up and out for 3am - had a very very noisy family near so unfortunately had no sleep. The Japanese Steak restaurant on site was amazing - shame about the family who kept us up as this would have warranted 5 stars

Reviewed on Jul 31, 2025

Cave Hotel & Golf Resort

Cave Hotel & Golf Resort

4 out of 5
per person
Sep 4 - Sep 10
found 10 hours ago
Roundtrip non-stop flight included
New York (JFK) to London (LGW)
9/10 Wonderful! (457 reviews)
Overall good stay, restaurant staff and cleaners were very polite and friendly. Very peaceful settings, easy parking. Loved the golfing range and price. Room was nice overall, modernised with electrical options for do not disturb, curtains, LED mirror, mattress and pillows were divine. Cleanliness (attention to detail) lacked at times, found a popped balloon under the seat upon check in, the drawers leather was peeling away and creaked whenever you opened or closed it, no toilet scrub brush, found hair in various places. Also, internet stopped working for like an hour one evening so couldn’t watch apps on tv. Pool and steam room area were well taken care of by cleaners, sweeping the water away and replacing towels etc. but the area itself is small, limited space to sit, in the pool there is only stairs to sit on other than 4 beds, jacuzzi bubbles very powerful so couldn’t have them on for long, under the stairs was quite rusty. Gym was small with limited facilities, but ok to go to in the morning when quiet. Forgot our sunglasses in the range area, they were not handed in to reception or the range staff unfortunately, so assumed to have been taken.

Reviewed on Jul 19, 2025

Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
per person
Sep 7 - Sep 12
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LGW)
8/10 Very Good! (1,003 reviews)
Friendly and professional staff Nice spa and pool

Reviewed on Jul 24, 2025

Don't see what you're looking for?
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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 top-notch restaurants 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

SEA LIFE Brighton

SEA LIFE Brighton

$26
per adult
SEA LIFE Brighton
From Brighton: Cambridge and Greenwich Day Trip

From Brighton: Cambridge and Greenwich Day Trip

$93
per adult
From Brighton: Cambridge and Greenwich Day Trip
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
$125 nightly
The price is $150 total per night from Aug 18 to Aug 19
$150 total
Aug 18 - Aug 19
Total includes taxes and fees
8.8/10 Excellent! (3,174 reviews)
"This is always a great stay for onward travel."

Reviewed on Jul 30, 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
$126 nightly
The price is $151 total per night from Aug 24 to Aug 25
$151 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (4,340 reviews)
Perfect for getting some shut-eye.
"The pitch black room was very welcoming after a long flight. It's small and there a bit of distance from reception but all was good."

Reviewed on Jul 30, 2025

Bloc Hotel London Gatwick Airport
Sofitel London Gatwick

Sofitel London Gatwick

4 out of 5
North Terminal, London Gatwick Airport, Gatwick, England
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $191 total per night from Aug 4 to Aug 5
$191 total
Aug 4 - Aug 5
Total includes taxes and fees
8.8/10 Excellent! (1,872 reviews)
"We always stay here when we are flying from Gatwick. The service is good and the rooms are comfortable and clean."

Reviewed on Aug 1, 2025

Sofitel London Gatwick
See all 3,370 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.

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Frequently asked questions

How much does a Chailey vacation package cost?
You'll find cheap prices from $746 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.