Top 10 Hotels in Chester, VT from ￥14,650 - Competitive Prices

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Our top choices for Chester hotels

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

A bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.

A variety of dishes including a steak, muffins, and a dessert with fruit.

A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.

1. Fullerton Inn

Chester Depot

Kirsty

￥25,035

￥27,288 total

includes taxes & fees

Oct 19 - Oct 20

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

A bedroom with a bed, a fireplace, a window, a dresser, and a clock on the wall.

A living room with two sofas, a fireplace, and a wooden floor.

A white house with a porch, wooden chairs, and an American flag.

2. Stone Hearth Inn and Eatery

Chester

John

￥34,574

￥37,685 total

includes taxes & fees

Sep 25 - Sep 26

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.

An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.

A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

3. Best Western Springfield Hotel

Springfield

Gerry

￥28,201

￥31,021 total

includes taxes & fees

Oct 18 - Oct 19

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

A room with a red sofa, armchairs, a coffee table, and a fireplace. There is a window with a view of trees and a chandelier.

A stone facade with a wooden door, steps leading up to a porch, and a small white chair outside.

A restaurant with a stone wall bar area, wooden tables, and chairs.

4. The Hartness House

Springfield

Dan

￥32,521

￥35,774 total

includes taxes & fees

Sep 28 - Sep 29

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

A Christmas tree decorated with lights, ornaments, and a bow.

A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

A bar area with a sign reading "MAGIC" and "featured Vermont beers".

5. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

￥16,037

￥18,362 total

includes taxes & fees

Sep 28 - Sep 29

A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

A picnic table with benches in a grassy area in front of a motel with multiple cars parked in the driveway.

A building with a 'Public Welcome' sign, a vending machine, and a hanging flower basket.

A reception desk with a check-in counter, a framed picture above it, and a potted plant to the right.

6. Claremont Motor Lodge

Claremont

EDWARD S

￥18,422

￥19,988 total

includes taxes & fees

Oct 25 - Oct 26

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A two-story white house with a front porch and a garage, surrounded by lush greenery.

A grassy field with a playground and trees in the background.

A hotel room with two beds, a desk, and a TV.

7. The Putney Inn

Putney

JANE

￥13,318

￥14,650 total

includes taxes & fees

Oct 25 - Oct 26

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

An indoor swimming pool with four chairs and a hot tub.

A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.

8. Pointe at Castle Hill Resort

Cavendish

Cristian

￥18,416

￥20,995 total

includes taxes & fees

Oct 25 - Oct 26

A large stone building with a steep roof, surrounded by dense forest and hills.

A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.

A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

9. Castle Hill Resort And Spa

Cavendish

Brandon

￥34,935

￥38,079 total

includes taxes & fees

Oct 18 - Oct 19

A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.

A cozy living room with a fireplace, wooden furniture, and large windows.

A house with a red exterior, large windows, and a well-maintained garden with various plants and flowers.

A spacious living room with wooden beams, a patterned sofa, a yellow armchair, and a red door.

10. COHO Inn & Motor Lodge

Weston

Raedene

￥32,309

￥35,217 total

includes taxes & fees

Sep 25 - Sep 26

A rustic dining area with wooden beams, tables, chairs, and a fireplace.

An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.

A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.

11. The Inn at Weathersfield

Perkinsville

Rula

￥38,388

￥47,667 total

includes taxes & fees

Oct 25 - Oct 26

A calm lake reflecting a forest with autumn foliage.

A modern house with a pool, surrounded by lush greenery and mountains in the background.

A house with a balcony and a garden with red flowers.

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

12. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

￥28,330

￥31,163 total

includes taxes & fees

Oct 25 - Oct 26

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

A hotel room with a bed, a desk, a chair, a wooden door, and a window.

A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

13. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

David

￥19,784

￥21,466 total

includes taxes & fees

Oct 25 - Oct 26

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

A metal bucket with a spoon, two wine glasses, and a checkered cloth on a brick ledge by a pool.

A banquet hall with multiple round tables set for dining, featuring chandeliers and brick walls.

A cozy room with a large bed, a fireplace, and a brick wall.

14. The Common Man Inn & Restaurant

Claremont

Victoria

￥29,058

￥31,529 total

includes taxes & fees

Oct 18 - Oct 19

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

An indoor swimming pool with a tiled deck, safety signs, and a few chairs.

15. Comfort Inn & Suites Brattleboro I-91

Brattleboro

John

￥22,696

￥24,965 total

includes taxes & fees

Sep 28 - Sep 29

A hotel room with two beds, a desk, a chair, a mirror, a TV, and a window with curtains.

A hotel room with a bed, a desk, a chair, a dresser, a mirror, a television, and a window with curtains.

An air conditioner with a control panel displaying temperature settings.

A coffee maker, a phone, and a coffee bag on a desk.

16. Royal Inn Claremont

Claremont

Eva

￥18,894

￥20,500 total

includes taxes & fees

Sep 28 - Sep 29

A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

A spacious lobby with a stone wall, a reception desk, and a large window.

A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

17. Hampton Inn Brattleboro

Brattleboro

Francesca

￥23,142

￥25,457 total

includes taxes & fees

Sep 30 - Oct 1

A hotel room with two beds, a TV, a desk, and a window with curtains.

A Days Inn with a brick facade, a central entrance, and a parking lot.

A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.

A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

18. Days Inn by Wyndham Keene NH

Keene

CHERYL

￥14,395

￥15,618 total

includes taxes & fees

Oct 25 - Oct 26

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

19. Best Western Plus Keene Hotel

Keene

Ruddy

￥22,000

￥23,871 total

includes taxes & fees

Oct 25 - Oct 26

A cozy living room with a fireplace, a coffee station, and a view of the outside.

A hotel room with two beds, a desk, a chair, a television, a dresser, and a door leading to a bathroom.

A motel with multiple floors, each with balconies and windows.

A hotel room with a sofa, a coffee table, a desk with a telephone, a mirror, and a television.

20. Colonial Motel

Brattleboro

Alida

￥13,094

￥14,403 total

includes taxes & fees

Sep 27 - Sep 28

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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

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

10/10 Excellent

"Very cool unique setting and property. The bed was like a cloud and very relaxing."

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."

Woodstock Inn & Resort

10/10 Excellent

"Wonderful inn! Everything was wonderful: rooms, food, etc!!"

Pointe at Castle Hill Resort

10/10 Excellent

"Very nice stay and nice rooms."

Hampton Inn and Suites Manchester

10/10 Excellent

"Wonderful relaxing stay!"

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."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"Nice"

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."

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."

More cheap stays in Chester

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)

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)

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)

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)

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

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)

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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Book Hotels in Chester on Expedia.com

Find hotels in Chester, VT from ￥14,650

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. The Upper Pass Lodge at Magic Mountain

6. Claremont Motor Lodge

7. The Putney Inn

8. Pointe at Castle Hill Resort

9. Castle Hill Resort And Spa

10. COHO Inn & Motor Lodge

11. The Inn at Weathersfield

12. Blue Gentian Lodge at Magic Mountain

13. Keene Elm City Hotel, an Ascend Collection Hotel

14. The Common Man Inn & Restaurant

15. Comfort Inn & Suites Brattleboro I-91

16. Royal Inn Claremont

17. Hampton Inn Brattleboro

18. Days Inn by Wyndham Keene NH

19. Best Western Plus Keene Hotel

20. Colonial Motel

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

The Equinox Golf Resort And Spa

Woodstock Inn & Resort

Pointe at Castle Hill Resort

Hampton Inn and Suites Manchester

Stone Hearth Inn and Eatery

Jackson Gore Village, A Vail Resorts Property

Latchis Hotel

The Jackson

More cheap stays in Chester

The Putney Inn

Aspen At Manchester

Latchis Hotel

The Manchester View

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn and Suites Manchester

Frequently asked questions

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