Chester Hotels from S$108

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28 Nov - 29 Nov
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28 Nov - 30 Nov
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Top 10 trending Chester hotels

Garden
Fullerton Inn

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very good, (402)
"Lovely stay"
United States
Christine
The price is S$182
includes taxes & fees
8 Dec - 9 Dec
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is S$263
includes taxes & fees
15 Dec - 16 Dec
Stone Hearth Inn and Eatery
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (552)
"Highly recommend stay here"
United States
Margie
The price is S$526
includes taxes & fees
30 Nov - 1 Dec
Woodstock Inn & Resort
Meeting facility
Aspen At Manchester

Aspen At Manchester

2.5 star property
Manchester Center
8.8 out of 10, Excellent, (604)
"Great place to stay"
United States
Brian
The price is S$172
includes taxes & fees
30 Nov - 1 Dec
Aspen At Manchester
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (886)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The Shire Woodstock
Individually decorated, desk, blackout curtains, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (544)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is S$167
includes taxes & fees
30 Nov - 1 Dec
Sleep Woodstock Motel
Front of property – evening/night
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1004)
"The hotel was clean, the staff was friendly, and was a great location. The new Brewery on the property was great as well!"
United States
Jake
The price is S$181
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn and Suites Manchester
Exterior
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, (856)
"Room was fantastic, had a lovely stay."
United States
Cody
The price is S$154
includes taxes & fees
9 Dec - 10 Dec
The Palmer House Resort, an Ascend Collection Hotel
Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (935)
"Great place for the price "
United States
Karen
The price is S$250
includes taxes & fees
7 Dec - 8 Dec
The Black Bear Lodge at Stratton Mountain Resort
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (571)
"Nice old Inn!"
United States
Daniel
The price is S$263
includes taxes & fees
7 Dec - 8 Dec
The Equinox Golf Resort & Spa
Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (918)
"Clean room, great staff, wonderful suggestions for area restaurants and attractions."
United States
Margie
The price is S$202
includes taxes & fees
30 Nov - 1 Dec
Pointe at Castle Hill Resort
Exterior
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4.0 star property
Manchester
9.4 out of 10, Exceptional, (814)
"Very nice, beautiful inn"
United States
Susan
The price is S$277
includes taxes & fees
1 Dec - 2 Dec
Kimpton Taconic Hotel by IHG
Property grounds
The Manchester View

The Manchester View

2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (772)
"Beautiful setting outside town, clean room, friendly staff, continental breakfast."
United States
Sylvia
The Manchester View
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

2.5 star property
Brattleboro
7.6 out of 10, Good, (1006)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is S$108
includes taxes & fees
1 Dec - 2 Dec
The Covered Bridge Inn
Outdoor dining
Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort

3.0 star property
Stratton
8.4 out of 10, Very good, (70)
"Amazing stay - The condo was cozy and perfect for our family! "
United States
Kate
The price is S$452
includes taxes & fees
30 Nov - 1 Dec
Vantage Point Villas at Stratton Mountain Resort
Free daily on-the-go breakfast
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1002)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is S$181
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Exterior
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (776)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
The price is S$149
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1008)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is S$385
includes taxes & fees
6 Dec - 7 Dec
On The River Inn
Front of property
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3.0 star property
West Dover
8.8 out of 10, Excellent, (242)
"Great place to stay!"
United States
Sonia
The price is S$178
includes taxes & fees
2 Dec - 3 Dec
Mount Snow Grand Summit Resort
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1006)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is S$196
includes taxes & fees
30 Nov - 1 Dec
Best Western Plus Keene 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.
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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

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.
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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.
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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.

See all hotels in Chester
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Great location Everything updated Pleasant greeting in lobby"
Amanda 1-night trip
Posted 3 days ago
Aspen At Manchester

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is S$129 per night from 28 Dec to 29 Dec
S$129
28 Dec - 29 Dec
includes taxes & fees
7/10 Good! (1,002 reviews)

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?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Kimpton Taconic Hotel by IHG 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. A top sight in the area is Stratton 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. Additionally, you'll find Stratton 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.

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