Find hotels in Chester, VT from AED 388

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1 Nov - 2 Nov
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14 Nov - 16 Nov

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Compare 2,997 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Garden
Fullerton Inn
Fullerton Inn
2.5 star property
8.2 out of 10, Very Good, (399)
"What an absolutely charming Inn. The room was very clean and comfortable, the food in the restaurant was outstanding, and the staff was wonderful. Overall, it was a great experience and I will definitely be back!"
United States
AJ
The price is AED 474
AED 516 total
includes taxes & fees
10 Nov - 11 Nov
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (105)
"Room was super quiet and clean. "
United States
Ernest
The price is AED 767
AED 836 total
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery
Lobby
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (545)
"This was our ideal hotel! Charmingly decorated, functional, and a walking distance to the town. We appreciated the complimentary champagne on our arrival, it was a wonderful place to spend our honeymoon."
United States
Evan and Nicole
The price is AED 1,172
AED 1,450 total
includes taxes & fees
30 Nov - 1 Dec
Woodstock Inn & Resort
Property grounds
The Shire Woodstock
The Shire Woodstock
3.0 star property
8.8 out of 10, Excellent, (870)
"Easy check-in / check-out. Very clean property and rooms. Easily walkable location to every major point of interest in Woodstock. Highly recommend the property. "
United States
Brendan
The Shire Woodstock
Meeting facility
Aspen At Manchester
Aspen At Manchester
2.5 star property
8.8 out of 10, Excellent, (598)
"Very nice hotel. Clean and looked recently remodeled. It was very quiet, allowing me to relax. Will stay here again when in the area."
United States
Grant
The price is AED 362
AED 438 total
includes taxes & fees
3 Nov - 4 Nov
Aspen At Manchester
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (539)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is AED 380
AED 580 total
includes taxes & fees
3 Nov - 4 Nov
Sleep Woodstock Motel
Exterior
The Palmer House Resort, an Ascend Collection Hotel
The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
8.4 out of 10, Very Good, (852)
"The area around the Palmer House is so beautiful. Mountains everywhere!! "
United States
Mark
The price is AED 372
AED 469 total
includes taxes & fees
4 Nov - 5 Nov
The Palmer House Resort, an Ascend Collection Hotel
Exterior detail
The Covered Bridge Inn
The Covered Bridge Inn
2.5 star property
7.6 out of 10, Good, (1003)
"Good value for a two night stay for work "
United States
jim
The price is AED 353
AED 388 total
includes taxes & fees
15 Nov - 16 Nov
The Covered Bridge Inn
Indoor spa tub
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.6 out of 10, Good, (930)
"Great place for the price "
United States
Karen
The price is AED 487
AED 589 total
includes taxes & fees
9 Nov - 10 Nov
The Black Bear Lodge at Stratton Mountain Resort
Front of property - evening/night
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1003)
"Very dog friendly."
United States
Gene
The price is AED 479
AED 527 total
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn and Suites Manchester
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
8.4 out of 10, Very Good, (1004)
"Hotel was great."
United States
Heidi
The price is AED 547
AED 594 total
includes taxes & fees
3 Nov - 4 Nov
Best Western Plus Keene Hotel
In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2.0 star property
7.0 out of 10, Good, (1003)
"Great stay"
United States
Michael
The price is AED 372
AED 403 total
includes taxes & fees
4 Nov - 5 Nov
Days Inn by Wyndham Keene NH
Indoor pool
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
8.8 out of 10, Excellent, (910)
"It was a beautiful place "
United States
Tony
The price is AED 473
AED 539 total
includes taxes & fees
3 Nov - 4 Nov
Pointe at Castle Hill Resort
Exterior
Kimpton Taconic Hotel by IHG
Kimpton Taconic Hotel by IHG
4.0 star property
9.4 out of 10, Exceptional, (811)
"Very nice, beautiful inn"
United States
Susan
The price is AED 555
AED 751 total
includes taxes & fees
4 Nov - 5 Nov
Kimpton Taconic Hotel by IHG
Exterior
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (562)
"Beautiful hotel! "
United States
sarah
The price is AED 404
AED 640 total
includes taxes & fees
12 Nov - 13 Nov
The Equinox Golf Resort & Spa
Sundeck
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (621)
"Loved my stay"
United States
Christine
The price is AED 559
AED 606 total
includes taxes & fees
4 Nov - 5 Nov
Riverside Hotel, an Ascend Collection Hotel
Property entrance
Jackson Gore Village
Jackson Gore Village
3.0 star property
8.6 out of 10, Excellent, (825)
"The hotel was peaceful and clean, perfect for the weekend getaway."
United States
Terrence
The price is AED 683
AED 830 total
includes taxes & fees
3 Nov - 4 Nov
Jackson Gore Village
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
8.8 out of 10, Excellent, (1006)
"The nicest Holiday Inn Express I have ever stayed at. Lovely place and super clean."
United States
WOODROW
The price is AED 522
AED 574 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Property grounds
The Manchester View
The Manchester View
2.5 star property
9.4 out of 10, Exceptional, (771)
"The setting is quiet peaceful and the accommodation is like home "
United States
diane
The price is AED 491
AED 540 total
includes taxes & fees
3 Nov - 4 Nov
The Manchester View
Outdoor dining
Vantage Point Villas at Stratton Mountain Resort
Vantage Point Villas at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (70)
"Great place to stay! We went on a last minute Father’s Day weekend trip and had the best time! Great location close to the shops and restaurants. "
United States
Roberta
The price is AED 841
AED 1,046 total
includes taxes & fees
6 Nov - 7 Nov
Vantage Point Villas at Stratton Mountain Resort
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, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Stay near popular Chester attractions

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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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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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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Great staff. Wonderful property, close to the village. "
Bruce 2-night trip
Posted 3 days ago
Woodstock Inn & Resort

More cheap stays in Chester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is AED 353 per night from Nov 15 to Nov 16
AED 353
AED 388 total
15 Nov - 16 Nov
includes taxes & fees
7.6/10 Good! (1,001 reviews)

Hotels in Chester with star-rating

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.
What's the top vacation rental that Chester has to offer?
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: Visitors like this Chester vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all 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.
Where can I learn more about changing or cancelling my trip to Chester?
For additional details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What's the best hotel for a family vacation to Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are also fun for kids of all ages. Find more child-friendly accommodations in Chester.
What's the best accommodation for a romantic vacation in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden. See all romantic hotels in Chester.
What's the best pet-friendly accommodation in Chester?
Motel in the Meadow is a top pet-friendly option for your stay. Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub is another good option for a stay with your pet. 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. Pointe at Castle Hill Resort and The Equinox Golf Resort & Spa are two additional hotels with an onsite pool. View all hotels with pools in Chester.
What's the best accommodation near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
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. In Chester, there are 67 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. You'll also find Grafton Historical Society and Vermont Country Store 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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