Top 10 Hotels in Chester, VT from ￥13,267 - Competitive Prices

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Pool

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Hot tub

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Our top choices for Chester hotels

Breakfast included

Hotel

Bed & breakfast

Reserve now, pay later

Pet friendly

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

1. Fullerton Inn

Chester Depot

Kirsty

￥21,929

￥23,903 total

includes taxes & fees

Aug 31 - Sep 1

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

2. Stone Hearth Inn and Eatery

Chester

Kathleen

￥32,954

￥35,920 total

includes taxes & fees

Aug 12 - Aug 13

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)

3. Best Western Springfield Hotel

Springfield

Gerry

￥28,256

￥31,082 total

includes taxes & fees

Aug 17 - Aug 18

4. The Hartness House

Springfield

Dan

￥30,465

￥33,512 total

includes taxes & fees

Aug 20 - Aug 21

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

5. Claremont Motor Lodge

Claremont

Shane

￥16,313

￥17,700 total

includes taxes & fees

Aug 10 - Aug 11

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

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

6. Pointe at Castle Hill Resort

Cavendish

Stephen

￥21,321

￥24,306 total

includes taxes & fees

Aug 10 - Aug 11

7. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

￥22,566

￥24,823 total

includes taxes & fees

Aug 10 - Aug 11

King Room with Spa Bath | Egyptian cotton sheets, premium bedding, memory foam beds, WiFi (free)

8. The Inn at Weathersfield

Perkinsville

LUDJANE

￥29,518

￥37,979 total

includes taxes & fees

Aug 10 - Aug 11

9. Harvest Barn Inn

Bellows Falls

Natalie

￥25,785

￥28,105 total

includes taxes & fees

Aug 19 - Aug 20

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

10. The Putney Inn

Putney

Robert

￥19,523

￥21,475 total

includes taxes & fees

Aug 10 - Aug 11

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

11. Bromley View Inn

Bondville

Josh

￥12,062

￥13,267 total

includes taxes & fees

Aug 10 - Aug 11

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

12. The Upper Pass Lodge at Magic Mountain

Londonderry

Bradley

￥13,722

￥15,231 total

includes taxes & fees

Sep 1 - Sep 2

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

13. The Common Man Inn & Restaurant

Claremont

Denis

￥21,156

￥22,954 total

includes taxes & fees

Sep 7 - Sep 8

Condo Hotel Room | Premium bedding, blackout drapes, iron/ironing board, WiFi (free)

Castle Queen Room | Premium bedding, blackout drapes, iron/ironing board, WiFi (free)

14. Castle Hill Resort And Spa

Cavendish

Nicholas

￥36,934

￥40,258 total

includes taxes & fees

Aug 11 - Aug 12

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

15. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Ramica

￥17,275

￥18,742 total

includes taxes & fees

Sep 2 - Sep 3

Coffee/tea maker, mini-fridge, microwave

16. Hampton Inn Brattleboro

Brattleboro

Kyle

￥19,275

￥21,203 total

includes taxes & fees

Aug 16 - Aug 17

Standard Room, 1 King Bed | View from room

17. Four Winds Country Motel

Manchester Center

CHARLES

￥24,528

￥26,980 total

includes taxes & fees

Sep 1 - Sep 2

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

Standard Room, 1 Queen Bed | Desk, blackout drapes, iron/ironing board, WiFi (free)

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

18. Royal Inn Claremont

Claremont

Eva

￥16,328

￥17,716 total

includes taxes & fees

Aug 12 - Aug 13

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)

19. Colonial Motel

Brattleboro

James

￥11,784

￥12,963 total

includes taxes & fees

Aug 10 - Aug 11

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

20. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

￥11,247

￥12,372 total

includes taxes & fees

Aug 11 - Aug 12

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Where to stay in Chester

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

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

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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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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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

Hampton Inn Brattleboro

10/10 Excellent

"Staff is very helpful"

Latchis Hotel

8/10 Good

"This was a nice stay. We had a very basic room. It was slightly outdated but that's not a bad thing. There's no outlet near the bed for your phone or anything. The bed was super comfortable. Our record player didn't work but it was a fun novelty. Sages, the bar attached to the hotel was really cool. Decorated awesome, great playlist, super comfy to have a drink in with very friendly staff. We didn't get to see a movie but we loved how the hotel lobby always smelled like popcorn and it was really beautifully decorated. We were concerned about parking but there was plenty of parking in the hotel's complimentary lot. The price was incredibly affordable and right in the middle of all the great shops and restaurants. Nothing was more than a 7 minute walk. Highly recommend!"

Hampton Inn and Suites Manchester

10/10 Excellent

"Celine was peasant and cheerful every time we arrived back at the hotel!"

Sleep Woodstock Motel

10/10 Excellent

"The property looks newly refurbished. Everything was in excellent shape, and the grounds were quite nice. And very clean. Also pet friendly. Would definitely recommend!"

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"As always, this place never disappoints. From the friendly staff that greets you at check-in, to the breakfast buffet that gives you a good variety to start your day… this will always be my go-to when visiting Keene."

Colonial Motel

8/10 Good

"Kind personnel, large green area. Breakfast is too basic though."

Claremont Motor Lodge

10/10 Excellent

"Nice small motel. Very clean and nicely maintained. Would recommend."

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Perfect"

Woodstock Inn & Resort

10/10 Excellent

"Amazing! Will visit again."

More cheap stays in Chester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

￥13,676

￥14,838 total

Sep 1 - Sep 2

includes taxes & fees

7/10 Good! (1,004 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

￥17,275

￥18,742 total

Sep 2 - Sep 3

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

￥17,788

￥19,567 total

Aug 10 - Aug 11

includes taxes & fees

8.6/10 Excellent! (948 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

￥19,275

￥21,203 total

Aug 16 - Aug 17

includes taxes & fees

8.2/10 Very Good! (1,005 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

￥20,564

￥22,620 total

Aug 31 - Sep 1

includes taxes & fees

8.6/10 Excellent! (845 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

￥23,825

￥26,208 total

Aug 30 - Aug 31

includes taxes & fees

9.6/10 Exceptional! (1,013 reviews)

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. Other good choices for your trip to the area are Woodstock Inn & Resort and Keene Elm City Hotel, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Chester.

What's the top vacation rental that Chester has to offer?

Okemo Mountain Lodging by Vail Resorts: You might want to consider this vacation home rental near Chester, which is in the mountains and offers cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. 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: Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants. Keene Elm City Hotel, an Ascend Collection Hotel and Kimpton Taconic Hotel by IHG 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.

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Book Hotels in Chester on Expedia.com

Find hotels in Chester, VT from ￥13,267

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Chester hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

4. The Hartness House

5. Claremont Motor Lodge

6. Pointe at Castle Hill Resort

7. Blue Gentian Lodge at Magic Mountain

8. The Inn at Weathersfield

9. Harvest Barn Inn

10. The Putney Inn

11. Bromley View Inn

12. The Upper Pass Lodge at Magic Mountain

13. The Common Man Inn & Restaurant

14. Castle Hill Resort And Spa

15. Keene Elm City Hotel, an Ascend Collection Hotel

16. Hampton Inn Brattleboro

17. Four Winds Country Motel

18. Royal Inn Claremont

19. Colonial Motel

20. The Covered Bridge Inn

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

DaVallia Art & Accents

Bonnie's Bundles Dolls

Learn more about Chester

Top Chester Hotel Reviews

Hampton Inn Brattleboro

Latchis Hotel

Hampton Inn and Suites Manchester

Sleep Woodstock Motel

Keene Elm City Hotel, an Ascend Collection Hotel

Colonial Motel

Claremont Motor Lodge

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Woodstock Inn & Resort

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Keene Elm City Hotel, an Ascend Collection Hotel

Latchis Hotel

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Hampton Inn and Suites Manchester

Frequently asked questions

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