Chester Hotels from S$99

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester hotels

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (112 reviews)
"So great all around!"
United States
Janet
The price is S$264
includes taxes & fees
17 Mar - 18 Mar
Stone Hearth Inn and Eatery

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (418 reviews)
"Great staff and service. "
United States
Chris
The price is S$178
includes taxes & fees
17 Mar - 18 Mar
Fullerton Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (56 reviews)
"Clean cozy rooms, overall good stay"
United States
Wade
The price is S$188
includes taxes & fees
11 Mar - 12 Mar
Hideaway Inn Mt. Snow

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (830 reviews)
"Very friendly staff. The room and all surroundings were clean and fresh smelling."
United States
Alison
The price is S$188
includes taxes & fees
1 Mar - 2 Mar
Best Western Springfield Hotel

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (74 reviews)
"Everything was really lovely, clean and nice. Loved the downstairs lounge and bar areas, so warm and relaxing. The host was extremely gracious. Looking forward to going back soon! "
United States
James
The Inn at Weathersfield

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (336 reviews)
"nice folks, practical place to stay. "
United States
Mark
The price is S$202
includes taxes & fees
1 Mar - 2 Mar
The Hartness House

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"An absolutely stunning property! The cabin was clean, well stocked and perfectly located to see the gorgeous sunrise. So very grateful for our quick trip at Fat Sheep Farm. Looking forward to returning! "
United States
Jasmine
Fat Sheep Farm & Cabins

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (578 reviews)
"Fantastic stay! Friendly staff, very cozy. "
United States
Nader
The price is S$257
includes taxes & fees
2 Mar - 3 Mar
The Olympia Lodge

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (534 reviews)
"Place and owners are awful"
United States
brian
The price is S$151
includes taxes & fees
24 Feb - 25 Feb
Four Winds Country Motel

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (331 reviews)
"Check-in was easy and the property is cute and very clean. "
United States
Karin
The price is S$147
includes taxes & fees
23 Feb - 24 Feb
Brittany Motel

Inn At Mount Snow

Inn At Mount Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (61 reviews)
"Place is spotless and.staff is amazing, will definitely be returning "
United States
hector
The price is S$198
includes taxes & fees
17 Mar - 18 Mar
Inn At Mount Snow

Toll Road Inn

Toll Road Inn
2.0 star property
Manchester Center
9.0 out of 10, Wonderful, (502 reviews)
"Location was great, clean, spacious room."
United States
Sheron
The price is S$199
includes taxes & fees
2 Mar - 3 Mar
Toll Road Inn

Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (748 reviews)
"Everything was great and we will stay there again 😁"
United States
Pasquale
The price is S$149
includes taxes & fees
24 Feb - 25 Feb
Weathervane Motel

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (60 reviews)
"Good place to stay. "
United States
steven
COHO Inn & Motor Lodge

Brook Bound Inn

Brook Bound Inn
2.0 star property
Wilmington
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful lodge very clean and comfortable "
United States
Virginia
Brook Bound Inn

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (71 reviews)
"Perfect for a quick overnight to go skiing at Stratton."
United States
Benjamin
The price is S$184
includes taxes & fees
2 Mar - 3 Mar
Stanford House

Farm Road Estate

Farm Road Estate
3.0 star property
West Dover
10.0 out of 10, Exceptional, (81 reviews)
"Amazing stay Beautiful room Great fireplace Close to mount snow Great service "
United States
Alessandra Mac Carthy
Farm Road Estate

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1,002 reviews)
"Very clean hotel! "
United States
Robert
The price is S$181
includes taxes & fees
15 Mar - 16 Mar
Hampton Inn and Suites Manchester

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
Manchester Center
8.4 out of 10, Very good, (899 reviews)
"Rooms were spotless and staff was great!"
United States
Helen
The price is S$132
includes taxes & fees
25 Feb - 26 Feb
The Palmer House Resort, an Ascend Collection Hotel
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.

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Chester

Find the best Chester areas for the activities you enjoy most.

Chester Depot

If you're spending some time in Chester Depot, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.

Stay near popular Chester attractions

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

More cheap stays in Chester

Frequently asked questions

Where is the best place to stay in Chester?
Stone Hearth Inn and Eatery is ranked highly by Expedia customers. This B&B offers free breakfast and free parking. Another top choice for your trip based on reviews is Fullerton Inn. See all available top hotels, or vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What's the best dog-friendly accommodation option in Chester?
Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.
What are some accommodation options with pools in Chester?
Pointe at Castle Hill Resort: Features a full-service spa, an indoor pool and free self parking. Woodstock Inn & Resort and The Equinox Golf Resort & Spa are two additional hotels that feature an on-site pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. Top sights around the area include Stratton Mountain Resort and Okemo Mountain Resort. In Chester, there are 68 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
A couple of favourite places to visit are Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort and Okemo Mountain Resort in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

Explore a world of travel with Expedia