Top 10 Hotels in Chester, VT from ₩141,146 - Competitive Prices

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Pet friendly

Pool

Apartment

Spa

Hot tub

Condo

Cottage

Family friendly

Waterpark

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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

₩227,533

₩248,011 total

includes taxes & fees

Sep 17 - Sep 18

2. Stone Hearth Inn and Eatery

Chester

John

₩281,227

₩306,538 total

includes taxes & fees

Sep 17 - Sep 18

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

3. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Amber

₩174,043

₩191,447 total

includes taxes & fees

Sep 20 - Sep 21

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

Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed) | Laptop workspace, iron/ironing board, rollaway beds (surcharge)

4. Best Western Springfield Hotel

Springfield

Gerry

₩240,997

₩265,095 total

includes taxes & fees

Sep 17 - Sep 18

Sauna, aromatherapy, hot stone massages, deep-tissue massages

Suite, 1 King Bed, Sofa Bed & Full Kitchen | Private kitchen | Coffee/tea maker

5. Pointe at Castle Hill Resort

Cavendish

David

₩216,291

₩246,573 total

includes taxes & fees

Sep 17 - Sep 18

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

6. The Common Man Inn & Restaurant

Claremont

Victoria

₩201,188

₩218,294 total

includes taxes & fees

Sep 17 - Sep 18

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

7. Harvest Barn Inn

Bellows Falls

Michael

₩249,431

₩271,880 total

includes taxes & fees

Sep 23 - Sep 24

Mansion Suite (Room 2) | Living area | 32-inch flat-screen TV with digital channels, TV, streaming services

8. The Hartness House

Springfield

Dan

₩240,243

₩264,267 total

includes taxes & fees

Sep 20 - Sep 21

9. Hampton Inn and Suites Manchester

Manchester Center

Tatiana

₩208,738

₩229,612 total

includes taxes & fees

Sep 22 - Sep 23

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Daniel

₩216,762

₩238,438 total

includes taxes & fees

Sep 20 - Sep 21

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

11. The Putney Inn

Putney

JANE

₩146,617

₩161,278 total

includes taxes & fees

Sep 20 - Sep 21

Premium bedding, desk, laptop workspace, blackout drapes

12. Best Western Plus Keene Hotel

Keene

Julia

₩200,606

₩217,664 total

includes taxes & fees

Sep 17 - Sep 18

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

13. Claremont Motor Lodge

Claremont

EDWARD S

₩175,026

₩189,903 total

includes taxes & fees

Sep 17 - Sep 18

Coffee/tea maker, mini-fridge, microwave

14. Hampton Inn Brattleboro

Brattleboro

Francesca

₩182,228

₩200,450 total

includes taxes & fees

Sep 28 - Sep 29

15. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

zhuang

₩213,895

₩255,363 total

includes taxes & fees

Sep 24 - Sep 25

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)

16. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

₩123,272

₩141,146 total

includes taxes & fees

Sep 17 - Sep 18

17. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

₩162,854

₩179,139 total

includes taxes & fees

Sep 17 - Sep 18

Room, 1 King Bed, Non Smoking | Blackout drapes, WiFi (free), bed sheets

18. Black Mountain Inn

Brattleboro

"Absolutely spotless room, the bedding was amazing, the beds were super comfortable. The people were the nicest people ever and we enjoyed them very much. We had a wonderful stay in Vermont. They advised us on where to dine, at the Marina and it was spot on amazing. We had breakfast at The Porch in the morning and the lovely girl even called to make sure they were open before we drove there. We had amazing food there as well."

Denise

₩172,570

₩189,827 total

includes taxes & fees

Sep 22 - Sep 23

Terrace Studio Two Queen Beds | Premium bedding, pillowtop beds, desk, iron/ironing board

One-Bedroom Suite King Bed | Premium bedding, pillowtop beds, desk, iron/ironing board

19. The Manchester View

Manchester Center

Jason

₩145,406

₩159,947 total

includes taxes & fees

Sep 21 - Sep 22

Deluxe House, 5 Bedrooms, Mountain View | Premium bedding, memory foam beds, desk, laptop workspace

Luxury Room, 2 Double Beds (Room 11) | Premium bedding, memory foam beds, desk, laptop workspace

20. Otherland Hotel

Newfane

Omar

₩114,265

₩167,107 total

includes taxes & fees

Sep 17 - Sep 18

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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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 Manchester View

10/10 Excellent

"Great place. Exceeded our expectations. The view, and surroundings are spectacular. And the "continental" breakfast was beyond continental. And it's dog friendly!!!"

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"Very clean. Staff were super helpful. Beautiful even though it was “off-season”."

The Shire Woodstock

10/10 Excellent

"Na"

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"Fun trip spa"

Hampton Inn and Suites Manchester

10/10 Excellent

"very clean inviting and pleasant staff"

Aspen At Manchester

10/10 Excellent

"Absolutely loved this property! Amazing location, super clean and spacious rooms! We loved being in close proximity to the town, which was soooooo amazingly pet friendly! We will definitely be back"

Colonial Motel

8/10 Good

"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."

The Equinox Golf Resort And Spa

10/10 Excellent

"Great property but a needs a little more tender care."

Stone Hearth Inn and Eatery

8/10 Good

"Wonderful staff and restaurant"

More cheap stays in Chester

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT

₩145,406

₩159,947 total

Sep 21 - Sep 22

includes taxes & fees

9.4/10 Exceptional! (896 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

₩147,224

₩161,946 total

Sep 21 - Sep 22

includes taxes & fees

Claremont Motor Lodge

16 Beauregard St Claremont NH

₩175,026

₩189,903 total

Sep 17 - Sep 18

includes taxes & fees

8.8/10 Excellent! (581 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

₩182,228

₩200,450 total

Sep 28 - Sep 29

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

₩208,738

₩229,612 total

Sep 22 - Sep 23

includes taxes & fees

9.6/10 Exceptional! (1,000 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

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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.

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. 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 64 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.

Explore a world of travel with Expedia

Book Hotels in Chester on Expedia.com

Find hotels in Chester, VT from ₩141,146

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. Comfort Inn & Suites Brattleboro I-91

4. Best Western Springfield Hotel

5. Pointe at Castle Hill Resort

6. The Common Man Inn & Restaurant

7. Harvest Barn Inn

8. The Hartness House

9. Hampton Inn and Suites Manchester

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

11. The Putney Inn

12. Best Western Plus Keene Hotel

13. Claremont Motor Lodge

14. Hampton Inn Brattleboro

15. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

16. The Upper Pass Lodge at Magic Mountain

17. The Covered Bridge Inn

18. Black Mountain Inn

19. The Manchester View

20. Otherland Hotel

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 Manchester View

Grand Summit Resort, A Vail Resorts Property

The Shire Woodstock

Jackson Gore Village, A Vail Resorts Property

Hampton Inn and Suites Manchester

Aspen At Manchester

Colonial Motel

The Equinox Golf Resort And Spa

Stone Hearth Inn and Eatery

More cheap stays in Chester

The Manchester View

Latchis Hotel

Claremont Motor Lodge

Hampton Inn Brattleboro

Hampton Inn and Suites Manchester

Keene Elm City Hotel, an Ascend Collection Hotel

Frequently asked questions

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