Bed and Breakfast in Chester

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Check prices for these dates

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

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 NZ$346
includes taxes & fees
1 Apr - 2 Apr
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

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 NZ$269
includes taxes & fees
26 Mar - 27 Mar
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 NZ$268
includes taxes & fees
25 Mar - 26 Mar
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 NZ$225
includes taxes & fees
2 Apr - 3 Apr
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)
"Beautiful location and nice staff."
United States
Cynthia
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 NZ$455
includes taxes & fees
26 Mar - 27 Mar
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 NZ$243
includes taxes & fees
2 Apr - 3 Apr
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 NZ$310
includes taxes & fees
25 Mar - 26 Mar
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 NZ$427
includes taxes & fees
1 Apr - 2 Apr
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 NZ$485
includes taxes & fees
15 Apr - 16 Apr
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 NZ$440
includes taxes & fees
25 Mar - 26 Mar
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 NZ$467
includes taxes & fees
25 Mar - 26 Mar
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 NZ$330
includes taxes & fees
26 Mar - 27 Mar
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 NZ$324
includes taxes & fees
26 Mar - 27 Mar
Big Bears Lodge
Dining

Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Manchester
9.0 out of 10, Wonderful, (2 reviews)
"For an overnight stay, this met our needs. The room was clean and had essential items. The little touches of a table and chairs, bench seat, and desk were useful! The 24 hour snack suite was cute and had the perfect amount of snacks and drinks before heading out to ski. There are plenty of restaurants 5 minutes away downtown. Two things to note: the bathroom is not big (sink & toilet are very low), if you are a tall person it might be a challenge. Also, the walls are very thin! We could hear the...
United States
Sandra A.
The price is NZ$223
includes taxes & fees
25 Mar - 26 Mar
Alpine 5, cozy Vermont retreat
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 NZ$386
includes taxes & fees
7 Apr - 8 Apr
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 NZ$442
includes taxes & fees
19 Apr - 20 Apr
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

8/10 Good
"Room was fine. Only stayed one night for a quick trip. Didn't realize that the restaurant was closed on Sundays. Was looking for a meal after a long drive, but there were plenty of places to eat in the area. "
Paul 1-night trip
Posted 7 hours ago
Best Western Plus Keene Hotel

Find out more about Chester

Chester B&B information

Number of reviews
1,914
Accommodation
62 B&B
Lowest Price
NZ$223
Highest Price
NZ$485

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, DaVallia Art & Accents and Bonnie's Bundles Dolls 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 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. 17.8 mi (28.6 km) from the city centre. 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. 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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