Chester Hotels

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Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

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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 P7,591
P8,274 total
includes taxes & fees
Nov 24 - Nov 25
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 P12,291
P13,398 total
includes taxes & fees
Nov 24 - Nov 25
Stone Hearth Inn and Eatery
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (551)
"Highly recommend stay here"
United States
Margie
The price is P19,360
P23,885 total
includes taxes & fees
Nov 30 - Dec 1
Woodstock Inn & Resort
Meeting facility
Aspen At Manchester

Aspen At Manchester

2.5 star property
Manchester Center
8.8 out of 10, Excellent, (602)
"Great place to stay"
United States
Brian
The price is P6,501
P7,797 total
includes taxes & fees
Dec 9 - Dec 10
Aspen At Manchester
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (885)
"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 price is P6,282
P7,325 total
includes taxes & fees
Nov 30 - Dec 1
The Shire Woodstock
2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (542)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is P4,872
P7,949 total
includes taxes & fees
Nov 23 - Nov 24
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, (1001)
"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 P7,485
P8,233 total
includes taxes & fees
Nov 30 - Dec 1
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 P5,492
P7,012 total
includes taxes & fees
Dec 2 - Dec 3
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 P8,768
P10,609 total
includes taxes & fees
Nov 23 - Nov 24
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, (570)
"Nice old Inn!"
United States
Daniel
The price is P7,955
P11,949 total
includes taxes & fees
Dec 7 - Dec 8
The Equinox Golf Resort & Spa
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 P9,368
P12,570 total
includes taxes & fees
Dec 1 - Dec 2
Kimpton Taconic Hotel by IHG
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 P9,945
P11,337 total
includes taxes & fees
Nov 23 - Nov 24
Pointe at Castle Hill Resort
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, (1003)
"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 P4,449
P4,893 total
includes taxes & fees
Nov 23 - Nov 24
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 P14,652
P18,213 total
includes taxes & fees
Nov 23 - Nov 24
Vantage Point Villas at Stratton Mountain 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, (1003)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is P8,179
P8,875 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Plus Keene Hotel
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, (1000)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is P7,485
P8,233 total
includes taxes & fees
Nov 25 - Nov 26
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1006)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is P9,993
P13,150 total
includes taxes & fees
Nov 24 - Nov 25
On The River Inn
Sundeck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (626)
"Clean room, beautiful location"
United States
Marcie
The price is P8,953
P9,714 total
includes taxes & fees
Dec 21 - Dec 22
Riverside Hotel, an Ascend Collection Hotel
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, (775)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
The price is P5,472
P6,767 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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 and neighborhoods 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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Very welcoming, spacious, clean. Perfect for a family of 4. "
Kathleen 2-night trip
Posted 4 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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 P5,802 per night from Dec 4 to Dec 5
P5,802
P6,295 total
Dec 4 - Dec 5
includes taxes & fees
7/10 Good! (1,001 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 visit 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 provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What's the best pet-friendly accommodation in Chester?
Motel in the Meadow is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.
What are some accommodations 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 with an onsite pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors to Chester are sure to enjoy the ski areas, coffeehouses, 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 accommodations to choose from. Find out more about Chester.
What should I see while I'm in Chester?
A couple of favorite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. Additionally, you'll find Stratton Mountain Resort in the area. Check out what more 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 temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.

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