Top 10 Hotels in Chester, VT from ₩116,483 - Competitive Prices

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Cottage

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Our top choices for Chester hotels

Iron/ironing board (on request), WiFi (free), bed sheets

1. Fullerton Inn

Chester Depot

Kirsty

₩192,326

₩209,635 total

includes taxes & fees

Sep 2 - Sep 3

Luxury Room, Mountain View | Blackout drapes, WiFi (free), individually decorated

2. Stone Hearth Inn and Eatery

Chester

Olena

₩289,016

₩315,027 total

includes taxes & fees

Sep 9 - Sep 10

Standard Room, 1 King Bed, Non Smoking | In-room safe, desk, iron/ironing board, cribs (free)

3. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Ingrid

₩186,019

₩201,837 total

includes taxes & fees

Sep 10 - Sep 11

Suite, 1 King Bed with Sofa bed, Non Smoking | Desk, blackout drapes, iron/ironing board, WiFi (free)

4. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Morgan

₩163,477

₩179,825 total

includes taxes & fees

Sep 7 - Sep 8

Premium bedding, desk, blackout drapes, iron/ironing board

5. The Common Man Inn & Restaurant

Claremont

Denis

₩185,546

₩201,319 total

includes taxes & fees

Sep 7 - Sep 8

Suite, 1 King Bed, Non Smoking, Jetted Tub | Laptop workspace, iron/ironing board, rollaway beds (surcharge)

6. Best Western Springfield Hotel

Springfield

Gerry

₩222,918

₩245,210 total

includes taxes & fees

Sep 2 - Sep 3

River View | Iron/ironing board (on request), WiFi (free), bed sheets

7. Harvest Barn Inn

Bellows Falls

Michael

₩240,833

₩262,507 total

includes taxes & fees

Aug 31 - Sep 1

Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, iron/ironing board, WiFi (free)

8. Claremont Motor Lodge

Claremont

Sergio

₩152,200

₩165,137 total

includes taxes & fees

Aug 30 - Aug 31

Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed | Premium bedding, WiFi (free), individually decorated

9. Bromley View Inn

Bondville

William

₩105,901

₩116,483 total

includes taxes & fees

Sep 1 - Sep 2

Coffee/tea maker, mini-fridge, microwave

10. Hampton Inn Brattleboro

Brattleboro

Timothy

₩155,148

₩170,663 total

includes taxes & fees

Sep 8 - Sep 9

Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds (surcharge), WiFi (free)

11. The Putney Inn

Putney

JANE

₩150,832

₩165,915 total

includes taxes & fees

Sep 1 - Sep 2

12. Black Mountain Inn

Brattleboro

Robert

₩164,821

₩181,303 total

includes taxes & fees

Aug 31 - Sep 1

Standard Double Room, 2 Double Beds, Refrigerator & Microwave | Desk, blackout drapes, iron/ironing board, WiFi (free)

13. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

₩96,301

₩105,931 total

includes taxes & fees

Sep 7 - Sep 8

Premium bedding, desk, laptop workspace, blackout drapes

14. Best Western Plus Keene Hotel

Keene

Julia

₩206,162

₩223,693 total

includes taxes & fees

Sep 7 - Sep 8

In-room safe, desk, blackout drapes, iron/ironing board

15. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Marnie

₩234,073

₩257,480 total

includes taxes & fees

Sep 13 - Sep 14

Suite, 1 King Bed with Sofa bed | Desk, blackout drapes, iron/ironing board, WiFi (free)

Deluxe Single Room, 1 King Bed | Desk, blackout drapes, iron/ironing board, WiFi (free)

16. Colonial Motel

Brattleboro

James

₩113,693

₩125,061 total

includes taxes & fees

Aug 30 - Aug 31

17. Days Inn by Wyndham Keene NH

Keene

Michael

₩134,225

₩145,634 total

includes taxes & fees

Sep 9 - Sep 10

Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer

Desk, blackout drapes, iron/ironing board, WiFi (free)

18. Sleep Woodstock Motel

Woodstock

John

₩117,056

₩128,762 total

includes taxes & fees

Aug 31 - Sep 1

19. Latchis Hotel

Brattleboro

Stark

₩167,722

₩184,494 total

includes taxes & fees

Aug 30 - Aug 31

Romantic Room, 1 Bedroom, Jetted Tub - Non-Pet Friendly | 1 bedroom, desk, iron/ironing board (on request), WiFi (free)

Exclusive Suite, 3 Bedrooms, Kitchenette, Mountain View - Pet Friendly | 1 bedroom, desk, iron/ironing board (on request), WiFi (free)

20. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

₩126,686

₩140,621 total

includes taxes & fees

Sep 1 - Sep 2

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Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.Learn more about Chester

Chester Depot

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.

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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.

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

Top Chester Hotel Reviews

The Shire Woodstock

10/10 Excellent

"The Shire is a great little inn, well maintained and close to all the amenities and restaurants at Woodstock. Rooms are tastefully furnished with comfortable bedding and linens. The coffee and tea station near the reception lobby is brilliant. There's a store right across the street and awesome coffee shops within walking distance. The only downside is that the mobile coverage in this area is very weak across most providers. We had to walk to town to get 4g access. The guest wifi does work though. We happened to lock ourselves out of the room late at night and had to call the staff (who were not on premises) for help us get back in - they were super nice about it and really prompt too. Recommend this place to anyone looking for a quaint little inn to explore the area! Love to come back here again!"

Hampton Inn and Suites Manchester

10/10 Excellent

"Very good breakfast, clean and spacious room, friendly staff."

Kimpton Taconic Hotel by IHG

10/10 Excellent

"Rooms were clean and comfortable ,staff was pleasant. Love the Manchester such a beautiful town."

Hampton Inn Brattleboro

8/10 Good

"Very clean. Good full breakfast."

Best Western Plus Keene Hotel

8/10 Good

"Clean room breakfast was good"

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"It was good!"

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"👍"

Colonial Motel

8/10 Good

"X"

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good

"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."

More cheap stays in Chester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

₩134,225

₩145,634 total

Sep 9 - Sep 10

includes taxes & fees

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

₩155,148

₩170,663 total

Sep 8 - Sep 9

includes taxes & fees

8.2/10 Very Good! (1,001 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

₩163,477

₩179,825 total

Sep 7 - Sep 8

includes taxes & fees

8.6/10 Excellent! (849 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

₩167,722

₩184,494 total

Aug 30 - Aug 31

includes taxes & fees

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

₩186,019

₩201,837 total

Sep 10 - Sep 11

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

₩214,437

₩235,881 total

Sep 8 - Sep 9

includes taxes & fees

9.6/10 Exceptional! (1,005 reviews)

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 Kimpton Taconic Hotel by IHG and Holiday Inn Club Vacations Mount Ascutney Resort by IHG. 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.

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 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 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 62 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.

Explore a world of travel with Expedia

Book Hotels in Chester on Expedia.com

Find hotels in Chester, VT from ₩116,483

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Keene Elm City Hotel, an Ascend Collection Hotel

4. Comfort Inn & Suites Brattleboro I-91

5. The Common Man Inn & Restaurant

6. Best Western Springfield Hotel

7. Harvest Barn Inn

8. Claremont Motor Lodge

9. Bromley View Inn

10. Hampton Inn Brattleboro

11. The Putney Inn

12. Black Mountain Inn

13. The Covered Bridge Inn

14. Best Western Plus Keene Hotel

15. Holiday Inn Express Hotel & Suites Brattleboro by IHG

16. Colonial Motel

17. Days Inn by Wyndham Keene NH

18. Sleep Woodstock Motel

19. Latchis Hotel

20. The Upper Pass Lodge at Magic Mountain

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

Bonnie's Bundles Dolls

DaVallia Art & Accents

Learn more about Chester

Top Chester Hotel Reviews

The Shire Woodstock

Hampton Inn and Suites Manchester

Kimpton Taconic Hotel by IHG

Hampton Inn Brattleboro

Best Western Plus Keene Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

Colonial Motel

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Latchis Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn and Suites Manchester

Frequently asked questions

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