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Sep 8 - Sep 9
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Sep 9 - Sep 10
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Sep 11 - Sep 13
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Sep 18 - Sep 20

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Our top choices for Chester hotels

Garden
Lobby sitting area
Dining
Front of property - evening/night

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
￥22,968
￥25,035 total
includes taxes & fees
Sep 10 - Sep 11
Fullerton Inn
Front of property
Luxury Room, Mountain View
Interior
Breakfast area

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
Kathleen
￥30,911
￥33,693 total
includes taxes & fees
Sep 16 - Sep 17
Stone Hearth Inn and Eatery
Exterior
Indoor pool
Breakfast area
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed)

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
￥24,835
￥27,318 total
includes taxes & fees
Sep 15 - Sep 16
Best Western Springfield Hotel
Spa
Suite, 1 King Bed, Sofa Bed & Full Kitchen | Private kitchen
Pool
Lobby lounge

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
David
￥19,304
￥22,006 total
includes taxes & fees
Sep 10 - Sep 11
Pointe at Castle Hill Resort
Lobby sitting area
Interior
Exterior
Restaurant

5. The Hartness House

The Hartness House
Springfield
United States
Dan
￥27,318
￥30,050 total
includes taxes & fees
Sep 10 - Sep 11
The Hartness House
Porch
Breakfast area
Exterior
River View

6. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
Michael
￥25,044
￥27,298 total
includes taxes & fees
Sep 11 - Sep 12
Harvest Barn Inn
Restaurant
Exclusive Suite, 3 Bedrooms, Kitchenette, Mountain View - Pet Friendly
Interior
Romantic Room, 1 Bedroom, Jetted Tub - Non-Pet Friendly

7. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
￥13,691
￥15,677 total
includes taxes & fees
Sep 9 - Sep 10
The Upper Pass Lodge at Magic Mountain
Exterior
Exterior
Property grounds
Standard Room, 2 Queen Beds, Refrigerator & Microwave

8. The Putney Inn

The Putney Inn
Putney
United States
JANE
￥16,787
￥18,466 total
includes taxes & fees
Sep 21 - Sep 22
The Putney Inn
Front of property
Castle Queen Room
Lobby lounge
Condo Hotel Room

9. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
￥30,324
￥33,053 total
includes taxes & fees
Sep 16 - Sep 17
Castle Hill Resort And Spa
Interior entrance
Meeting facility
Terrace/patio
Room

10. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Victoria
￥21,365
￥23,181 total
includes taxes & fees
Sep 13 - Sep 14
The Common Man Inn & Restaurant
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave
Exterior
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave
Lobby

11. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
EDWARD S
￥18,128
￥19,669 total
includes taxes & fees
Sep 9 - Sep 10
Claremont Motor Lodge
Front of property
Reception
Exterior
Living area

12. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
￥27,470
￥29,943 total
includes taxes & fees
Sep 13 - Sep 14
COHO Inn & Motor Lodge
Standard Room, 2 Double Beds
Room
Standard Room, 1 Queen Bed
Bathroom

13. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
￥17,342
￥18,816 total
includes taxes & fees
Sep 9 - Sep 10
Royal Inn Claremont
Lobby
Pool
Lobby
Suite, 1 King Bed with Sofa bed, Non Smoking

14. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Amber
￥18,462
￥20,309 total
includes taxes & fees
Sep 20 - Sep 21
Comfort Inn & Suites Brattleboro I-91
Interior
King Room with Spa Bath
Terrace/patio
King Room with Garden View

15. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
￥26,224
￥34,256 total
includes taxes & fees
Sep 10 - Sep 11
The Inn at Weathersfield
Restaurant
Property amenity
Property amenity
Lobby

16. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Julia
￥22,968
￥24,921 total
includes taxes & fees
Sep 15 - Sep 16
Best Western Plus Keene Hotel
Terrace Studio Two Queen Beds
The Corner Residence
One-Bedroom Suite King Bed
Point of interest

17. The Manchester View

The Manchester View
Manchester Center
United States
Jason
￥12,973
￥14,269 total
includes taxes & fees
Sep 9 - Sep 10
The Manchester View
Kayaking
Spa
Property grounds
Outdoor pool

18. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
￥23,283
￥25,611 total
includes taxes & fees
Sep 10 - Sep 11
Blue Gentian Lodge at Magic Mountain
Pool
Private kitchen
Restaurant
Lobby

19. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Timothy
￥19,092
￥21,002 total
includes taxes & fees
Sep 20 - Sep 21
Hampton Inn Brattleboro
Front of property - evening/night
Snack bar
Lobby
Exterior

20. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Tatiana
￥24,217
￥26,640 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Inn and Suites Manchester
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Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.
A forest with autumn foliage in various colors.

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

Bonnie's Bundles Dolls

7.6/10 (4 reviews)
This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.
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DaVallia Art & Accents

10.0/10 (2 reviews)
This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
See properties

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
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"Breathtaking views, beautiful property. Very relaxing and had everything needed in the room. Would certainly stay here again. Loved whet everything about this inn."
Kimberly 2-night trip
Posted 5 hours ago
The Manchester View
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Na"
Kevin M 1-night trip
Posted 11 hours ago
Hampton Inn and Suites Manchester
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Beautiful property, really special! Easy walk to shops."
crystal 1-night trip
Posted 13 hours ago
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Bel endroit pour passer du temps avec la famille."
Mariline 2-night trip
Posted 15 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Lovely room for a quick stay! Staff was so kind and accommodating! 10/10 Highly recommend!"
Genevieve 1-night trip
Posted 15 hours ago
The Shire Woodstock
The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 1 day ago
The Jackson
Latchis Hotel

Latchis Hotel

10/10 Excellent
"Considering the age of the property, this is a great stay! The staff was super helpful upon arrival, helping with check-in, parking and directions. The proximity to shops and restaurants is amazing. The room was clean and comfortable. I love that there were extra fans in the room to account for the lack of AC. Definitely still stay again!"
Caitlin 2-night trip
Posted 2 days ago
Latchis Hotel
On The River Inn

On The River Inn

10/10 Excellent
"Very nice. Breakfast is just an ordinary meal buffet."
Orrin 1-night trip
Posted 2 days ago
On The River Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"I found this interesting "resort" by accident when I needed to spend time with my mom who was about 40 minutes away in the Lebanon/Hancock, NH area. Wished I'd had more time to spend at there! I would have brought a bathing suit, tried the hot tub, booked a massage at the Spa, and had another delicious meal at the restaurant in the historic building. The non-historic lodging part of the property seems more like a place families and couples might stay when they ski: very comfortable and casual, older (but not historic), not too fancy, allows dogs!! Staff was lovely! Nice, friendly, available for questions, and willing to make more coffee when I slept in and everyone else beat to me to it."
Melissa 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort

More cheap stays in Chester

The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
￥12,973
￥14,269 total
Sep 9 - Sep 10
includes taxes & fees
9.4/10 Exceptional! (883 reviews)
The Manchester View
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
￥15,759
￥17,336 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (976 reviews)
Latchis Hotel
Claremont Motor Lodge

Claremont Motor Lodge

16 Beauregard St Claremont NH
￥18,128
￥19,669 total
Sep 9 - Sep 10
includes taxes & fees
Claremont Motor Lodge
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
￥19,092
￥21,002 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Hampton Inn Brattleboro
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
￥24,217
￥26,640 total
Sep 21 - Sep 22
includes taxes & fees
9.6/10 Exceptional! (1,003 reviews)
Hampton Inn and Suites Manchester
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
Get ratesKeene Elm City Hotel, an Ascend Collection Hotel

Frequently asked questions

Where is the best place to stay in Chester?
Located 25.2 mi (40.5 km) from the heart of Chester, Woodstock Inn & Resort is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Latchis Hotel and Grand Summit Resort, A Vail Resorts Property. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental that Chester has to offer?
5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow: Visitors like this Chester vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. 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?
Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top pet-friendly option for your stay. Motel in the Meadow is another good choice for you and 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. On The River Inn and Keene Elm City Hotel, an Ascend Collection Hotel 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 63 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 Vermont Country Store and Lowell Lake State Park 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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