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

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

kris

฿5,009

฿5,460 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

2. Stone Hearth Inn and Eatery

Chester

John

฿9,481

฿10,334 total

includes taxes & fees

8 Oct - 9 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 sitting area, a bathroom with a bathtub, and a large mirror.

A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.

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

3. Best Western Springfield Hotel

Springfield

Gerry

฿5,113

฿5,625 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 kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

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

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

4. Pointe at Castle Hill Resort

Cavendish

Cristian

฿4,963

฿5,657 total

includes taxes & fees

21 Oct - 22 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

Rula

฿7,621

฿9,544 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 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 living room with a fireplace, two armchairs, a TV mounted above the fireplace, and a desk with a mirror and lamp.

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

6. The Hartness House

Springfield

Elizabeth

฿6,697

฿7,367 total

includes taxes & fees

1 Nov - 2 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 swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.

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

7. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

฿4,944

฿5,438 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.

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

8. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Jessica

฿6,057

฿7,359 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 room with a wooden table, two chairs, a vase with flowers, a hanging plant, a framed picture on the wall, and a patterned rug.

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

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.

9. Harvest Barn Inn

Bellows Falls

gail

฿5,115

฿5,575 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Paul

฿5,110

฿5,621 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 living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

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.

11. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

฿3,530

฿4,042 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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.

12. The Common Man Inn & Restaurant

Claremont

Bruce

฿4,357

฿4,727 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 lobby with a reception desk, seating area, and a wall with framed pictures.

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.

13. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

฿3,805

฿4,185 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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 chair.

14. The Manchester View

Manchester Center

Isaac

฿2,842

฿3,126 total

includes taxes & fees

3 Nov - 4 Nov

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

A lobby with wooden paneling, a fireplace, and two green armchairs.

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.

15. Hampton Inn Brattleboro

Brattleboro

Francesca

฿3,943

฿4,338 total

includes taxes & fees

1 Nov - 2 Nov

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

A bar area with a fireplace, seating, and a TV.

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

16. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

฿5,829

฿6,325 total

includes taxes & fees

25 Oct - 26 Oct

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

A bar area with a hexagonal tiled wall, a wooden planter with greenery, a metal tray with cookies, and a menu board on the wall.

A bar area with a long counter, green upholstered bar stools, and a variety of bottles and glasses on shelves.

17. Main and Mountain Bar & Motel

Ludlow

Patricia

฿6,789

฿7,468 total

includes taxes & fees

13 Oct - 14 Oct

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

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

18. Castle Hill Resort And Spa

Cavendish

Brandon

฿9,046

฿9,861 total

includes taxes & fees

19 Oct - 20 Oct

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

A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

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

฿4,715

฿5,116 total

includes taxes & fees

1 Nov - 2 Nov

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 hot tub on a covered porch with a view of autumn foliage.

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

20. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

฿5,009

฿5,510 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

Hideaway Inn Mt. Snow

8/10 Good

"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"Allen in the restaurant is great."

Jackson Gore Village, A Vail Resorts Property

8/10 Good

"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"

On The River Inn

10/10 Excellent

"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."

The Jackson

10/10 Excellent

"Evelyn & Oakes was top notch."

Woodstock Inn & Resort

10/10 Excellent

"Clean rooms, very friendly staff, noise AC"

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good

"Older property that needs updating. Beds were very comfortable."

Aspen At Manchester

10/10 Excellent

"Great place, but a bit over priced for what it is"

Fullerton Inn

10/10 Excellent

"Great place. Made our anniversary amazing. Thank you"

More cheap stays in Chester

The Putney Inn

57 Putney Landing Rd Putney VT

฿2,829

฿3,112 total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

The Manchester View

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

฿2,842

฿3,126 total

3 Nov - 4 Nov

includes taxes & fees

Aspen At Manchester

5669 Main Street Manchester Center VT

฿3,472

฿4,189 total

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (699 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

฿4,000

฿4,340 total

2 Nov - 3 Nov

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

฿4,765

฿5,242 total

1 Nov - 2 Nov

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

฿4,944

฿5,438 total

1 Nov - 2 Nov

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 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 ฿2,330

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. Holiday Inn Express Hotel & Suites Brattleboro by IHG

11. The Upper Pass Lodge at Magic Mountain

12. The Common Man Inn & Restaurant

13. Comfort Inn & Suites Brattleboro I-91

14. The Manchester View

15. Hampton Inn Brattleboro

16. Fairfield Inn & Suites by Marriott Keene Downtown

17. Main and Mountain Bar & Motel

18. Castle Hill Resort And Spa

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

Hideaway Inn Mt. Snow

Grand Summit Resort, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

On The River Inn

The Jackson

Woodstock Inn & Resort

The Palmer House Resort, an Ascend Collection Hotel

Aspen At Manchester

Fullerton Inn

More cheap stays in Chester

The Putney Inn

The Manchester View

Aspen At Manchester

Keene Elm City Hotel, an Ascend Collection Hotel

Latchis Hotel

Hampton Inn and Suites Manchester

Frequently asked questions

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