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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (128 reviews)
"Wonderful staff and restaurant"
United States
John
The price is S$357
includes taxes & fees
30 Sept - 1 Oct
Stone Hearth Inn and Eatery
A calm lake reflecting a forest with autumn foliage.

2. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (125 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is S$237
includes taxes & fees
29 Sept - 30 Sept
Blue Gentian Lodge at Magic Mountain
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

3. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (46 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
The price is S$259
includes taxes & fees
20 Oct - 21 Oct
Windham Hill Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

4. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (57 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is S$201
includes taxes & fees
29 Sept - 30 Sept
Four Columns Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

5. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (104 reviews)
"Beautiful property! The charm and character of the place were amazing. Staff was friendly and very helpful. Rooms were quaint and well appointed, clean with comfy beds!"
United States
Amanda
The price is S$443
includes taxes & fees
13 Oct - 14 Oct
Echo Lake Inn
A bedroom with a bed, dresser, TV, and a chair.

6. Doveberry Inn

Doveberry Inn
3.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
The price is S$152
includes taxes & fees
27 Oct - 28 Oct
Doveberry Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

7. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (359 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is S$197
includes taxes & fees
30 Sept - 1 Oct
Colonel Williams Inn
A wooden table set with plates, cutlery, and a folded napkin.

8. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is S$194
includes taxes & fees
11 Oct - 12 Oct
The Carriage Barn Inn
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

9. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (133 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is S$174
includes taxes & fees
29 Sept - 30 Sept
Deerfield Valley Inn
A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

10. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (218 reviews)
"Welcoming host with great customer service"
United States
Alfred
The price is S$242
includes taxes & fees
29 Sept - 30 Sept
Big Bears Lodge
A house with a red roof, a porch with white railings, and a blue door.

11. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67 reviews)
"Great place to stay"
United States
eric
The price is S$695
includes taxes & fees
29 Sept - 30 Sept
Woodbridge Inn
A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

12. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (383 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
The price is S$371
includes taxes & fees
25 Oct - 26 Oct
The Inn at Manchester
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

13. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (323 reviews)
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
United States
Laura
The price is S$328
includes taxes & fees
26 Oct - 27 Oct
The Jackson
A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

14. The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is S$422
includes taxes & fees
1 Oct - 2 Oct
The One Cat B&B
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

15. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is S$587
includes taxes & fees
29 Sept - 30 Sept
Deer Brook Inn
A large, two-story house with a snow-covered driveway and surrounding trees.

16. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
The price is S$417
includes taxes & fees
18 Oct - 19 Oct
Chesterfield Inn
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

17. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (172 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is S$504
includes taxes & fees
29 Sept - 30 Sept
The Inn at Ormsby Hill
A living room with a grey sectional sofa, a potted plant, and a radiator.

18. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (79 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is S$290
includes taxes & fees
26 Oct - 27 Oct
The Vesper
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"We will be back. Wonderful staff and great location."
Melissa 1-night trip
Posted 12 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester B&B information

Number of reviews
2,037
Accommodation
36 B&B
Lowest Price
S$152
Highest Price
S$695

Frequently asked questions

Searching for B&Bs in Chester?
If you're hoping for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your trip. When you want to explore some attractions in town, Bonnie's Bundles Dolls and DaVallia Art & Accents are worth a stop.
Are you considering an apartment for your stay?
With attentive service, opportunities to meet guests from other places and delectable breakfasts, B&Bs all have a unique setting.
What are the top B&Bs in Chester?
Here are some B&Bs in the surrounding 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 decor. Bromley View Inn: 16 rooms. Situated 17.8 mi (28.6 km) from the heart of Chester. Enjoy the unique decor and fireplace in reception.
How many bed & breakfasts should I expect to find in Chester?
Expedia has 5 B&Bs for your getaway in Chester.
What's the best time of year to stay at a B&B in Chester?
When you're dreaming of a getaway to Chester, make sure that you take the year-round temperatures into account. 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.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you'll definitely enjoy Chester for its coffee shops and restaurants. If you're looking to find something to do during your travels, you might consider visiting Bonnie's Bundles Dolls and DaVallia Art & Accents. You might also consider a trip to sites such as 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 centre. You can also search 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, consider renting a car to explore more sights.

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