Chester Holiday Rentals, Vermont: Private House Rentals

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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 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.

A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.

1. Fullerton Inn

Chester Depot

kris

฿4,340

฿4,730 total

includes taxes & fees

9 Nov - 10 Nov

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

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

A conference room with a long wooden table, multiple chairs, and a large window providing natural light.

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

2. Stone Hearth Inn and Eatery

Chester

John

฿9,487

฿10,341 total

includes taxes & fees

12 Oct - 13 Oct

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 sofa, a coffee table, a desk, and a TV.

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.

3. Best Western Springfield Hotel

Springfield

Gerry

฿5,117

฿5,629 total

includes taxes & fees

1 Nov - 2 Nov

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

A spacious lobby with a fireplace, leather seating, and a chandelier.

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

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

4. Pointe at Castle Hill Resort

Cavendish

Cristian

฿5,126

฿5,844 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

A living room with a sofa, ottoman, armchair, and a television on a stand.

5. The Inn at Weathersfield

Perkinsville

Dorrie

฿7,627

฿9,551 total

includes taxes & fees

4 Nov - 5 Nov

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

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.

A living room with a fireplace, two armchairs, a TV mounted above the fireplace, and a desk with a mirror and lamp.

6. The Hartness House

Springfield

Elizabeth

฿6,702

฿7,372 total

includes taxes & fees

8 Nov - 9 Nov

A two-story building with a patio area featuring outdoor seating and a stone fire pit.

A spacious living area with a fireplace, comfortable seating, and a stone accent wall.

A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

A swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.

7. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

฿5,118

฿5,630 total

includes taxes & fees

8 Nov - 9 Nov

A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

A golf course with rolling hills, trees, and a distant mountain range.

A hotel with a swimming pool area, including two hot tubs and lounge chairs.

A hot tub with a tiled interior and a window in the background.

8. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Jessica

฿6,061

฿7,364 total

includes taxes & fees

26 Oct - 27 Oct

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

A dining area with a table and chairs, a window with a view of trees, a potted plant, and a door with a view of a mountain.

A two-story white house with a porch, a front yard, and a mailbox.

A room with a wooden table, two chairs, a vase with flowers, a hanging plant, a framed picture on the wall, and a patterned rug.

9. Harvest Barn Inn

Bellows Falls

gail

฿5,118

฿5,579 total

includes taxes & fees

1 Nov - 2 Nov

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 hotel room with a large bathtub, a bed with a colorful quilt, two bedside lamps, and a framed picture on the wall.

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

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

10. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

฿3,165

฿3,624 total

includes taxes & fees

12 Oct - 13 Oct

A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

11. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

฿4,676

฿5,144 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A wooden interior with a pool, benches, and a clock.

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

12. The Common Man Inn & Restaurant

Claremont

Bruce

฿4,360

฿4,730 total

includes taxes & fees

1 Nov - 2 Nov

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 room with a sofa, a coffee table, a chair, a desk, and a lamp.

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

13. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

฿3,722

฿4,094 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

A bar area with a dark wooden bar, multiple bar stools, and a large screen displaying the hotel name.

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

14. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

฿5,833

฿6,329 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a fireplace, two beds, a chair, and a nightstand.

A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.

A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.

A living room with a fireplace, a sofa, a coffee table, a cabinet, and two chairs.

15. The Manchester View

Manchester Center

Jan

฿3,407

฿3,747 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

16. Castle Hill Resort And Spa

Cavendish

Brandon

฿9,053

฿9,867 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

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

17. Hampton Inn Brattleboro

Brattleboro

Francesca

฿3,860

฿4,246 total

includes taxes & fees

8 Nov - 9 Nov

A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.

A multi-story hotel with balconies, a ski slope in the background, and a clear blue sky.

A dining area with a wooden table and chairs, a window with a view, and a bookshelf with books and decorative items.

A bar area with wooden ceiling, shelves with bottles, and a bar counter.

18. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Glen

฿4,348

฿4,782 total

includes taxes & fees

5 Nov - 6 Nov

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.

A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

19. Hampton Inn & Suites Keene

Keene

Rebecca

฿5,204

฿5,646 total

includes taxes & fees

25 Oct - 26 Oct

A calm lake reflecting a forest with autumn foliage.

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

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

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

20. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

฿5,012

฿5,514 total

includes taxes & fees

3 Nov - 4 Nov

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Where to stay in Chester

Find the best Chester areas 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, 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.

See all hotels in Chester

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

Top Chester Hotel Reviews

Latchis Hotel

10/10 Excellent

"Very unique and quaint"

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good

"Raymond was great at check in"

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"We only stayed one night, we arrived at dark and left in the morning because we were just stopping on our way to Maine. When we walked outside the next morning and actually saw the property at daylight we were blown away at the beautiful views. The fall colors were breathtaking. The rooms were clean, the beds were comfortable. I would love to come back and stay a few days and just take everything in."

Hideaway Inn Mt. Snow

10/10 Excellent

"This place was great! Super cute and clean"

Fullerton Inn

10/10 Excellent

"Clean rooms"

Colonial Motel

8/10 Good

"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."

Stone Hearth Inn and Eatery

8/10 Good

"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps"

The Manchester View

8/10 Good

"The lodge was in a picturesque location with lots of amenities. The rooms were clean apart from bugs in the window seals and in the main community areas. Lots of spider webs in lamp shades and around window areas. Just seemed to be overlooked for a long time. Unfortunately, we did not have a window screen on our room window in order to cool the room off due to the AC unit not functioning properly. We did find a fan which helped some. The breakfast was delicious and it was overall a comfortable place to stay and relax. I would definitely return for the views and location. Hopefully with the new staff in place, the lodge will improve in other areas needing attention."

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"Allen in the restaurant is great."

More cheap stays in Chester

The Putney Inn

57 Putney Landing Rd Putney VT

฿2,831

฿3,114 total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (1,004 reviews)

The Manchester View

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

฿3,407

฿3,747 total

3 Nov - 4 Nov

includes taxes & fees

9.4/10 Exceptional! (923 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

฿4,003

฿4,343 total

2 Nov - 3 Nov

includes taxes & fees

Aspen At Manchester

5669 Main Street Manchester Center VT

฿4,161

฿4,947 total

9 Nov - 10 Nov

includes taxes & fees

8.8/10 Excellent! (699 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

฿4,768

฿5,245 total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,005 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

฿5,118

฿5,630 total

8 Nov - 9 Nov

includes taxes & fees

9.6/10 Exceptional! (1,004 reviews)

Frequently asked questions

Where is the best place to stay in Chester?

Based on our traveller 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 visit. 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 if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What's the best dog-friendly accommodation option in Chester?

Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.

What are some accommodation options with pools in Chester?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Aspen At Manchester and The Manchester View are two additional hotels that feature an on-site pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 67 hotels and other accommodation options to choose from. Find out more about Chester.

What should I do while I'm visiting Chester?

A couple of favourite 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. Take a look at what more there is 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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Book Hotels in Chester on Expedia.com

Find hotels in Chester, VT from ฿2,987

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. Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

5. The Inn at Weathersfield

6. The Hartness House

7. Hampton Inn and Suites Manchester

8. Jackson Gore Village, A Vail Resorts Property

9. Harvest Barn Inn

10. The Upper Pass Lodge at Magic Mountain

11. Holiday Inn Express Hotel & Suites Brattleboro by IHG

12. The Common Man Inn & Restaurant

13. Comfort Inn & Suites Brattleboro I-91

14. Fairfield Inn & Suites by Marriott Keene Downtown

15. The Manchester View

16. Castle Hill Resort And Spa

17. Hampton Inn Brattleboro

18. Sun Lodge near Manchester VT, Ascend Collection Hotel

19. Hampton Inn & Suites Keene

20. Blue Gentian 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

Latchis Hotel

The Palmer House Resort, an Ascend Collection Hotel

Jackson Gore Village, A Vail Resorts Property

Hideaway Inn Mt. Snow

Fullerton Inn

Colonial Motel

Stone Hearth Inn and Eatery

The Manchester View

Grand Summit Resort, A Vail Resorts Property

More cheap stays in Chester

The Putney Inn

The Manchester View

Keene Elm City Hotel, an Ascend Collection Hotel

Aspen At Manchester

Latchis Hotel

Hampton Inn and Suites Manchester

Frequently asked questions

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