Chester Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Chester

Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3 out of 5
698 VT-11, Chester, VT
Fully refundableReserve now, pay when you stay
The price is S$263 per night from 27 Nov to 28 Nov
S$263
includes taxes & fees
27 Nov - 28 Nov
9/10 Wonderful! (73 reviews)
"If you’re looking for an authentic experience in a 200 year old home - with tons of wonderful history and true early American character - you’ll love this stay! This is NOT a shiny new hotel, with all the conveniences. You can forget your free “make-your-own hot breakfast” deal. This chef-curated ..."

Reviewed on 12 Oct,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 S$502 per night from 16 Dec to 17 Dec
S$502
includes taxes & fees
16 Dec - 17 Dec
9.2/10 Wonderful! (483 reviews)
"The overall experience was great."

Reviewed on 20 Nov,2024

Woodstock Inn & Resort
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is S$205 per night from 8 Dec to 9 Dec
S$205
includes taxes & fees
8 Dec - 9 Dec
9.6/10 Exceptional! (1,001 reviews)
"Convenient, very clean, friendly staff and great breakfast!"

Reviewed on 21 Nov,2024

Hampton Inn and Suites Manchester
See all 2,871 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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.