Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to £335 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Your Chester Holiday

Excellent adventures await when you reserve a Chester holiday package. Whether you're a history buff, art enthusiast or just a traveller who loves to experience new places, there's something for everyone in this lively city. Need some ideas on what to see or do first during your trip to Chester? Don't miss leading attractions like DaVallia Art & Accents. Your ultimate Chester holiday is just clicks away. Search flights, accommodation and more on Expedia for a trip that's tailored to suit your travel style.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
3,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Okemo Mountain Resort, Weston Playhouse and Weston Priory

Our pick of the best Chester Hotel Deals

Fullerton Inn
Fullerton Inn
2.5 out of 5
40 The Common, Chester, VT
Stay at this inn in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
8/10 Very Good! (355 reviews)
"We enjoyed our stay at this lovely Inn, it was quiet and the owner was welcoming and knowledgeable about the area. Our youngest especially enjoyed the checkerboard in the lounge"

Reviewed on 9 Jun 2025

Fullerton Inn
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (519 reviews)
Stunning
"Always a stunning stay in Woodstock!"

Reviewed on 2 Jun 2025

Woodstock Inn & Resort
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool and a full-service spa. Our guests praise the property condition in their ...
7.2/10 Good! (482 reviews)
"The facility is lovely. As much as the coffee set up near the lobby was good it is still better to have one in the room when you first wake up. The TV reception could be improved if possible. Watching Ladies golf tournament and when the 18th hole deciding game it lost connection, other than that ..."

Reviewed on 5 Jun 2025

The Equinox Golf Resort & Spa
See all 2,976 properties in Chester
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
Tailor make your Chester travel package from as little as . Choose from any combination of hotels, flights and rental cars to put together the getaway you’ve been dreaming about for ages. Don’t forget to add on one or two experiences!
If I'm not able to travel, can I cancel my Chester travel package?
We get it — life doesn’t always go according to plan. If you’ve locked in a Chester travel package and need to change or cancel it, we can help. We recommend taking a look at our Customer Service Portal first for information. But in general, if you’ve booked your package within 24 hours, you may be able to cancel or change your itinerary for free. If it’s more than 24 hours, your airline, hotel or car rental company may impose a fee.
How do I get a cheap travel package to Chester?
Just imagine all the fun things you could do in Chester with a wad of extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and other bookings into a Chester travel package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 properties around the globe. Whether you’re enjoying a break with the whole family or adventuring alone, organising a trip to Chester is better with a package.
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn’t stop you from escaping on holiday, so Expedia has come up with a solution to help. Now that we’ve partnered with online lender Klarna, it’s easier than ever to book a dream getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budget sizes, so you can escape on that well-earned holiday now.
  • Pay in instalments holidays: If you’d like to pay off your escape across multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you come across an unbeatable deal but your budget doesn’t quite cover it yet, Klarna’s low deposit holiday plan will help you lock in your getaway.

Where should I stay in Chester?
If you plan to visit DaVallia Art & Accents, skip commuting and lock in a hotel close by. It’s one of the best attractions in Chester.
What are the top hotels in Chester?
Fullerton Inn in the Chester Depot neighbourhood is a wonderful choice for a Chester getaway. Check in here and you’ll be well-positioned to get out and discover all that this colourful city has to offer.
How far in advance should I book my Chester holiday?
Browse Expedia to compare international flights as soon as you’ve got your travel dates. You can usually purchase a seat up to 12 months before departure. If you can’t see your preferred carrier, or you’ve left things to the last minute, fear not. Cheap fares to Chester occasionally appear within weeks of departure.
What does an Expedia Chester travel package include?
That depends on what type of trip you’re thinking about. Chester holiday deals can include flights, car rentals and hotels. You can mix and match to find the package that works for you! You can also add on experiences and activities after you’ve booked to get even bigger discounts.
What should I know before booking a Chester travel package?
We already have low prices. However, you’ll enjoy even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with a Chester Expedia travel package?
Yes — that’s one of the best things about an Expedia package. You’re in control. We have access to more than 550 airline partners around the world, so you have lots of choice when organising your Chester escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.