Chester Holidays

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Your Chester Holiday

When a city stay is calling your name, answer it with a holiday package to Chester. With all your travel plans in place before you leave, all you have to do here is concentrate on making unforgettable memories. A trip to Chester wouldn't be complete without exploring a few well-known attractions, like DaVallia Art & Accents. Stop dreaming and start travelling. Explore the broad range of options on Expedia today and finally put your Chester holiday plans into gear!

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

The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$157 per night from 19 May to 20 May
AU$157
per night
19 May - 20 May
8.2/10 Very Good! (1,002 reviews)
"Fantastic staff, for the price it's an excellent value. Grocery and common shopping close. Downtown Brattleboro 5 minutes away. Great food everywhere, Kipling Taverns top shelf dinner."

Reviewed on 9 May 2024

The Covered Bridge Inn
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
2 out of 5
698 VT-11, Chester, VT
Fully refundableReserve now, pay when you stay
The price is AU$384 per night from 12 May to 13 May
AU$384
per night
12 May - 13 May
9/10 Wonderful! (48 reviews)
After the eclipse
"Vicky and her family are wonderful hosts. We stayed on the last day of their season and received as welcoming a reception as you might expect at the height of the season. Stonehearth Inn is a labor of love and it shows."

Reviewed on 10 Apr. 2024

Stone Hearth Inn and Eatery
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$480 per night from 12 May to 13 May
AU$480
per night
12 May - 13 May
9.2/10 Wonderful! (441 reviews)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."

Reviewed on 3 May 2024

Woodstock Inn & Resort
See all 2,944 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

All Inclusive Holidays
beach holidays

Beach Holidays

Beach Holidays
family friendly holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chester holiday package cost?
Get ready to book, because a trip to Chester starts from an affordable . When you bundle your flights, hotels and more into a package, you’ll land the best deals.
How do I get a cheap travel package to Chester?
Bundling your hotel and flight with Expedia won’t just save you time — it’ll save you a pretty penny too. A Chester holiday package makes it easy to create your perfect trip. With more than 550 airlines all over the world to select from, finding flights that suit your busy schedule won’t be a hassle. Not only that, we have over 1 000 000 properties globally to take your pick of. Talk about choice! No matter who you are, Expedia will help show you the world.
Where should I stay in Chester?
If you’ll be checking out DaVallia Art & Accents, skip commuting and book a hotel room nearby. It’s one of the most popular attractions in the area.
What are the top hotels in Chester?
Many people opt to stay at Fullerton Inn in Chester Depot. If it’s your very first time in Chester, you’re guaranteed a warm welcome here.
How far in advance should I book my Chester holiday?
To land discount prices, book early. Air carriers generally advertise flight tickets, along with some of the lowest fares, around a year prior to departure. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway in Chester, there are always lots of great deals on Expedia. Check them out now!
What does an Expedia Chester travel package include?
Rental cars, hotels and flights — we’ve got them well covered. With Expedia, you can shape your Chester travel package just how you like it. All you have to do is determine just what you need. Once you’ve made your booking, you can add on fun things like activities and tours. The more you bundle, the greater your savings!
What should I know before booking a Chester travel package?
Whether it’s relaxation or adventure you’re craving, a Chester holiday package lets you organise your escape your way. Plus, you’ll score great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you’ll save!
Can I choose my airline with a Chester Expedia holiday package?
Expedia has access to more than 550 partner airlines globally, so you definitely can. Just pick the airline you want and craft your ideal Chester escape.
If I'm not able to travel, can I cancel my Chester holiday package?
Yes, it’s possible to cancel your Chester booking if your travel plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Chester

Image for Bonnie's Bundles Dolls

Bonnie's Bundles Dolls

Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views or seek out its ski slopes.

Bonnie's Bundles Dolls
Image for DaVallia Art & Accents

DaVallia Art & Accents

Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.

DaVallia Art & Accents
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.