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Check prices for these dates

Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12
In one month
Apr 24 - Apr 26
In two months
May 22 - May 24

Our top choices for Chester bed & breakfast

Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (115 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is NT$6,667
NT$7,267 total
includes taxes & fees
Mar 24 - Mar 25
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (434 reviews)
"Great place to stay. I really loved the place."
United States
Simon
Bromley View Inn
Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is NT$5,027
NT$5,530 total
includes taxes & fees
Mar 26 - Mar 27
Colonel Williams Inn
Property grounds

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (117 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is NT$4,756
NT$5,232 total
includes taxes & fees
Mar 24 - Mar 25
Blue Gentian Lodge at Magic Mountain
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NT$4,434
NT$4,811 total
includes taxes & fees
Mar 31 - Apr 1
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (25 reviews)
"Clean, spacious and well decorated. A pleasure to spend time in."
United States
Elizabeth
Four Columns Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (255 reviews)
"Harvest Barn Inn was the perfect place to stay warm on a freezing Vermont winter weekend. We absolutely loved the cozy atmosphere - homemade cookies, endless tea, plenty of books, and beautiful views. The three-course weekend breakfast was the highlight of our stay. Blessing and Kaelan were very communicative and friendly hosts. "
United States
Hannah
Harvest Barn Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is NT$7,980
NT$8,778 total
includes taxes & fees
Mar 26 - Mar 27
The One Cat B&B
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
The price is NT$5,386
NT$5,925 total
includes taxes & fees
Mar 30 - Mar 31
The Vesper
Exterior

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (301 reviews)
"Staff was exceptionally friendly…lovely Inn! Beautiful views "
United States
Michael
The price is NT$5,267
NT$5,793 total
includes taxes & fees
Mar 24 - Mar 25
The Inn at Manchester
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is NT$7,426
NT$8,169 total
includes taxes & fees
Apr 1 - Apr 2
Deer Brook Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (275 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is NT$8,245
NT$9,069 total
includes taxes & fees
Apr 15 - Apr 16
The Jackson
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (115 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
Deerfield Valley Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is NT$7,488
NT$8,237 total
includes taxes & fees
Mar 24 - Mar 25
Inn on Putney Road
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is NT$7,948
NT$8,743 total
includes taxes & fees
Mar 24 - Mar 25
Stay At Jimmy's
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (40 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is NT$6,033
NT$6,576 total
includes taxes & fees
Mar 24 - Mar 25
Windham Hill Inn
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (208 reviews)
"Very friendly and close to the mountain "
United States
Richard
The price is NT$5,506
NT$6,057 total
includes taxes & fees
Mar 25 - Mar 26
Big Bears Lodge
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is NT$7,357
NT$8,019 total
includes taxes & fees
Apr 6 - Apr 7
Echo Lake Inn
Front of property - evening/night

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (158 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is NT$8,267
NT$9,094 total
includes taxes & fees
Mar 24 - Mar 25
The Inn at Ormsby Hill
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

6/10 Okay
"All staff we encountered were friendly & accommodating. The room itself was pleasant and clean but the bathroom was in bad need of an update and it appeared unclean due to rust and missing bolt covers on the toilet."
Kathy 1-night trip
Posted 3 hours ago
Best Western Plus Keene Hotel

Find out more about Chester

Chester B&B information

Number of reviews
1,912
Accommodation
34 B&B
Lowest Price
NT$4,811
Highest Price
NT$9,094

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 well-liked 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. 17.8 mi (28.6 km) from the heart of downtown. 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.

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