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Our top choices for Chester bed & breakfast

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

1. Stone Hearth Inn and Eatery

Chester

John

P19,229 total

includes taxes & fees

Oct 5 - Oct 6

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

2. Harvest Barn Inn

Bellows Falls

Mary

P10,373 total

includes taxes & fees

Nov 2 - Nov 3

A cozy room with a fireplace, green sofas, a pool table, and a lamp.

3. Bromley View Inn

Bondville

William

P5,627 total

includes taxes & fees

Nov 1 - Nov 2

A calm lake reflecting a forest with autumn foliage.

4. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

P10,252 total

includes taxes & fees

Nov 1 - Nov 2

A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

5. Windham Hill Inn

West Townshend

Nadine

P12,672 total

includes taxes & fees

Oct 20 - Oct 21

A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

6. Echo Lake Inn

Plymouth

Amanda

P22,367 total

includes taxes & fees

Oct 13 - Oct 14

A bedroom with a bed, dresser, TV, and a chair.

7. Doveberry Inn

West Dover

Veronica

P8,360 total

includes taxes & fees

Oct 25 - Oct 26

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

8. The Jackson

West Woodstock

Laura

P9,688 total

includes taxes & fees

Nov 3 - Nov 4

A living room with a grey sectional sofa, a potted plant, and a radiator.

9. The Vesper

Woodstock

Keith

P11,353 total

includes taxes & fees

Oct 25 - Oct 26

A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

10. The Inn at Manchester

Manchester Village Historic District

Reagan

P11,039 total

includes taxes & fees

Nov 1 - Nov 2

A large white building with a stone wall and a lawn covered in fallen leaves.

11. Colonel Williams Inn

Brattleboro

Amy

P10,837 total

includes taxes & fees

Oct 6 - Oct 7

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

12. Four Columns Inn

Newfane

Raymond

P7,290 total

includes taxes & fees

Nov 2 - Nov 3

A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

13. Deerfield Valley Inn

West Dover

Patrick

P7,219 total

includes taxes & fees

Nov 1 - Nov 2

A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

14. Big Bears Lodge

West Dover

Alfred

P11,870 total

includes taxes & fees

Oct 4 - Oct 5

A wooden table set with plates, cutlery, and a folded napkin.

15. The Carriage Barn Inn

Keene

Jonathan

P11,455 total

includes taxes & fees

Oct 4 - Oct 5

A modern fitness center with exercise equipment, mirrors, and a reception area.

16. Stay At Jimmy's

Woodstock

Jeanne

A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

17. Deer Brook Inn

Woodstock

Laurence

P16,008 total

includes taxes & fees

Nov 2 - Nov 3

A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

18. The One Cat B&B

Brattleboro

marjie

P20,642 total

includes taxes & fees

Oct 7 - Oct 8

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Top Chester Hotel Reviews

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

The Jackson

10/10 Excellent

"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

Find out more about Chester

Chester B&B information

Number of reviews	3,058
Accommodation	35 B&B
Lowest Price	P5,627
Highest Price	P22,367

Frequently asked questions

Searching for B&Bs in Chester?

If you're looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop.

Are you thinking about B&Bs over traditional hotel rooms?

With attentive service, opportunities to mingle with other guests, and hearty breakfasts, B&Bs provide a unique setting.

What are the top B&Bs in Chester?

Here are some B&Bs in the area: Stone Hearth Inn and Eatery: 8 rooms. 1.5 mi (2.3 km) from the heart of Chester. Enjoy the free buffet breakfast and unique décor. Bromley View Inn: 16 rooms. Situated 17.8 mi (28.6 km) from the heart of Chester. Enjoy the unique décor and fireplace in the lobby.

How many Bed & Breakfasts should I expect to find in Chester?

Expedia has 5 B&Bs for your stay in Chester.

What's the best time of year to stay at a B&B in Chester?

When you're dreaming of a escape to Chester, be sure to take into account the year-round temperatures. 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.

What is there to do in Chester?

If you like to experience a new place through your taste buds, you'll be sure to enjoy Chester for its coffeehouses and restaurants. If you're looking to find something to do during your travels, you might consider checking out DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites like Vermont Country Store or Lowell Lake State Park if you have time to see more of the area.

How can I get to and around Chester?

You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city center. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester bed & breakfast

1. Stone Hearth Inn and Eatery

2. Harvest Barn Inn

3. Bromley View Inn

4. Blue Gentian Lodge at Magic Mountain

5. Windham Hill Inn

6. Echo Lake Inn

7. Doveberry Inn

8. The Jackson

9. The Vesper

10. The Inn at Manchester

11. Colonel Williams Inn

12. Four Columns Inn

13. Deerfield Valley Inn

14. Big Bears Lodge

15. The Carriage Barn Inn

16. Stay At Jimmy's

17. Deer Brook Inn

18. The One Cat B&B

Top Chester Hotel Reviews

The Shire Woodstock

Pointe at Castle Hill Resort

Jackson Gore Village, A Vail Resorts Property

The Jackson

Colonial Motel

The Palmer House Resort, an Ascend Collection Hotel

On The River Inn

Aspen At Manchester

The Equinox Golf Resort And Spa

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Search B&B in Chester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester bed & breakfast

1. Stone Hearth Inn and Eatery

2. Harvest Barn Inn

3. Bromley View Inn

4. Blue Gentian Lodge at Magic Mountain

5. Windham Hill Inn

6. Echo Lake Inn

7. Doveberry Inn

8. The Jackson

9. The Vesper

10. The Inn at Manchester

11. Colonel Williams Inn

12. Four Columns Inn

13. Deerfield Valley Inn

14. Big Bears Lodge

15. The Carriage Barn Inn

16. Stay At Jimmy's

17. Deer Brook Inn

18. The One Cat B&B

Top Chester Hotel Reviews

The Shire Woodstock

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia