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Sep 24 - Sep 25
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Sep 25 - Sep 26
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Sep 25 - Sep 27
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Oct 2 - Oct 4

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
¥25,035
¥27,288 total
includes taxes & fees
Oct 19 - Oct 20
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
¥34,574
¥37,685 total
includes taxes & fees
Sep 25 - Sep 26
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
¥28,201
¥31,021 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Springfield Hotel

4. The Hartness House

The Hartness House
Springfield
United States
Dan
¥32,521
¥35,774 total
includes taxes & fees
Sep 28 - Sep 29
The Hartness House

5. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
¥16,037
¥18,362 total
includes taxes & fees
Sep 28 - Sep 29
The Upper Pass Lodge at Magic Mountain

6. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
EDWARD S
¥18,422
¥19,988 total
includes taxes & fees
Oct 25 - Oct 26
Claremont Motor Lodge

7. The Putney Inn

The Putney Inn
Putney
United States
JANE
¥13,318
¥14,650 total
includes taxes & fees
Oct 25 - Oct 26
The Putney Inn

8. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
¥18,416
¥20,995 total
includes taxes & fees
Oct 25 - Oct 26
Pointe at Castle Hill Resort

9. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
¥34,935
¥38,079 total
includes taxes & fees
Oct 18 - Oct 19
Castle Hill Resort And Spa

10. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
¥32,309
¥35,217 total
includes taxes & fees
Sep 25 - Sep 26
COHO Inn & Motor Lodge

11. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
¥38,388
¥47,667 total
includes taxes & fees
Oct 25 - Oct 26
The Inn at Weathersfield

12. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
¥28,330
¥31,163 total
includes taxes & fees
Oct 25 - Oct 26
Blue Gentian Lodge at Magic Mountain

13. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
David
¥19,784
¥21,466 total
includes taxes & fees
Oct 25 - Oct 26
Keene Elm City Hotel, an Ascend Collection Hotel

14. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Victoria
¥29,058
¥31,529 total
includes taxes & fees
Oct 18 - Oct 19
The Common Man Inn & Restaurant

15. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
John
¥22,696
¥24,965 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Brattleboro I-91

16. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
¥18,894
¥20,500 total
includes taxes & fees
Sep 28 - Sep 29
Royal Inn Claremont

17. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Francesca
¥23,142
¥25,457 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn Brattleboro

18. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
¥14,395
¥15,618 total
includes taxes & fees
Oct 25 - Oct 26
Days Inn by Wyndham Keene NH

19. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
¥22,000
¥23,871 total
includes taxes & fees
Oct 25 - Oct 26
Best Western Plus Keene Hotel

20. Colonial Motel

Colonial Motel
Brattleboro
Canada
Alida
¥13,094
¥14,403 total
includes taxes & fees
Sep 27 - Sep 28
Colonial Motel
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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

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.
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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
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
"Very cool unique setting and property. The bed was like a cloud and very relaxing."
David B 1-night trip
Posted 12 hours ago
The Manchester View
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 20 hours ago
The Equinox Golf Resort And Spa
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 1 day ago
Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Wonderful relaxing stay!"
Rosemary 2-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

10/10 Excellent
"Our group of four ladies had an excellent time at the historic Stone Hearth Inn. We stayed in a lovely room with 4 single beds. They were very accommodating, including a late check-in and breakfast. Breakfast included homemade bread and other fresh food in a beautiful setting overlooking the lush backyard. It is a family run operation. We were checked in and served breakfast by Vicki, because her son Edward , daughter Georgia and son-in-law Conner were all working at the local Chester Festival. We really enjoyed meeting and getting to know Vicky. We did sample fresh made donuts and pretzels at the festival. They were amazing! The room was clean and comfortable. Unfortunately, we did not get to eat in the restaurant because it was closed during the festival. We are all certain that the food there would’ve been excellent as both Georgia and Connor are master chefs. All four of us ladies highly recommend this gem in beautiful Chester, Vermont. In any season, it’s a beautiful, relaxing place to stay while exploring the things available nearby, including historic, towns and buildings, covered bridges, hiking, skiing, and great food."
Alison 2-night trip
Posted 2 days ago
Stone Hearth Inn and Eatery
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Nice"
Thomas 3-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property
Latchis Hotel

Latchis Hotel

10/10 Excellent
"WE enjoyed the architecture of the whole complex - reception coffee lounge (Hot Drinks day and night as a compliment). Parking was right there. Center of town. The staff helped us when we needed to extend at the special rate. It attracts fun guests. It is a special place - not the run of the mill franchise. The linen is first class, nice thick towels. The room had a microwave and a refrig, plus the record player theme is another theme for folks who appreciate the vinyl era. Remember - Art Deco Era - not modern era."
Kris 6-night trip
Posted 3 days ago
Latchis Hotel
The Jackson

The Jackson

8/10 Good
"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."
Robin 1-night trip
Posted 3 days ago
The Jackson

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
¥13,318
¥14,650 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The Putney Inn
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
¥15,797
¥19,116 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (691 reviews)
Aspen At Manchester
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
¥19,022
¥20,924 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (989 reviews)
Latchis Hotel
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
¥19,023
¥20,925 total
Oct 22 - Oct 23
includes taxes & fees
9.4/10 Exceptional! (905 reviews)
The Manchester View
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
¥19,784
¥21,466 total
Oct 25 - Oct 26
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
¥28,724
¥31,596 total
Oct 22 - Oct 23
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Hampton Inn and Suites Manchester

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveler data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Stone Hearth Inn and Eatery is another good choice for your stay. 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?
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. The Manchester View and Pointe at Castle Hill Resort 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 66 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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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