Chester Holidays from £748

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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.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
per person
16 Oct - 19 Oct
found 20 hours ago
Return flight included
London (LON) to Springfield (VSF)
6.8/10 (1,001 reviews)
Always a pleasure to stay at the Colonial

Reviewed on 28 Jul 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
per person
16 Oct - 19 Oct
found 20 hours ago
Return flight included
London (LON) to Springfield (VSF)
9.4/10 Exceptional! (50 reviews)
everybody was so kind! we had a wonderful room for such a cheap price, I couldn't resist to choose this inn. The house keeper was so sweet and so was the owner! I will definitely be coming back :)

Reviewed on 29 Jul 2025

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 out of 5
per person
16 Oct - 19 Oct
found 20 hours ago
Return flight included
London (LON) to Springfield (VSF)
6/10 (682 reviews)
the room was not clean. there was never anyone around at the front desk. there was construction under way upstairs. the towels were old and small. not enough pillows.

Reviewed on 9 Jul 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
16 Oct - 19 Oct
found 20 hours ago
Return flight included
London (LON) to Springfield (VSF)
8.6/10 Excellent! (202 reviews)
I stayed in July when it was 95° and super humid so I appreciated the extra cold air conditioning! I don’t know why they put us in a room so so so far away from the main entrance but other than that long walk, everything was fine that’s super fabulous or anything just fine. The front desk didn’t really know much but we were only there for a night so we figured things out on our own. Definitely go to Trail 87 to eat when you visit here. It’s fantastic!

Reviewed on 15 Jul 2025

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
per person
16 Oct - 19 Oct
found 20 hours ago
Return flight included
London (LON) to Springfield (VSF)
8/10 Very Good! (1,002 reviews)
This hotel was fine for a night's stay, but we didn't enjoy the damp smell of our room, and it's showing the wear of years.

Reviewed on 27 Jul 2025

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

Top hotels in Chester

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
The price is £115 per night from 1 Sept to 2 Sept
£115
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (369 reviews)
"It’s not like anyplace I have stayed before. It’s so homey and very comfortable. The staff is very friendly and it’s clean as a whistle."

Reviewed on 25 Jul 2025

Fullerton Inn
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester, VT
9.8/10 Exceptional! (23 reviews)
Hidden gem!
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"

Reviewed on 24 Feb 2025

Get rates
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is £374 per night from 1 Sept to 2 Sept
£374
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (528 reviews)
"Really enjoyed our stay."

Reviewed on 18 Jul 2025

Woodstock Inn & Resort
See all 2,966 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
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Frequently asked questions

How much does a Chester travel package cost?
Tailor make your Chester travel package from as little as £748. 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.