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Check prices for these dates

Next weekend
13 Feb - 15 Feb
In two weeks
20 Feb - 22 Feb
In one month
6 Mar - 8 Mar
In two months
3 Apr - 5 Apr

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, (111 reviews)
"So great all around!"
United States
Janet
The price is RM1,108
RM1,208 total
includes taxes & fees
5 Feb - 6 Feb
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (420 reviews)
"Clean room/ great breakfast"
United States
Ryan
Bromley View Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (19 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (247 reviews)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (344 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is RM619
RM681 total
includes taxes & fees
17 Feb - 18 Feb
Colonel Williams Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is RM546
RM592 total
includes taxes & fees
5 Feb - 6 Feb
The Carriage Barn Inn
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (287 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is RM649
RM713 total
includes taxes & fees
10 Feb - 11 Feb
The Inn at Manchester
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (264 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Kayaking

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113 reviews)
"Lovely pleasant stay. "
United States
Heather
The price is RM704
RM774 total
includes taxes & fees
5 Feb - 6 Feb
Blue Gentian Lodge at Magic Mountain
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is RM590
RM649 total
includes taxes & fees
11 Feb - 12 Feb
The One Cat B&B
Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very good, (38 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 RM743
RM810 total
includes taxes & fees
17 Feb - 18 Feb
Windham Hill Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is RM730
RM803 total
includes taxes & fees
8 Feb - 9 Feb
The Vesper
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is RM922
RM1,014 total
includes taxes & fees
8 Feb - 9 Feb
Inn on Putney Road
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is RM924
RM1,016 total
includes taxes & fees
3 Mar - 4 Mar
Deer Brook Inn
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (195 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is RM701
RM771 total
includes taxes & fees
5 Feb - 6 Feb
Big Bears Lodge
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, (154 reviews)
"Love this place! Have stayed here twice now and will again. Great location, beautiful rooms, delicious breakfast and very friendly owners. A+"
United States
cynthia
The price is RM900
RM990 total
includes taxes & fees
18 Feb - 19 Feb
The Inn at Ormsby Hill
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (102 reviews)
"Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel."
Canada
Shane
Deerfield Valley Inn
Front of property – evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is RM1,208
RM1,311 total
includes taxes & fees
5 Feb - 6 Feb
Chesterfield Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is RM1,175
RM1,293 total
includes taxes & fees
9 Feb - 10 Feb
Stay At Jimmy's
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

On The River Inn

On The River Inn

10/10 Excellent
"Everything was amazing from the room to the pool to the restaurant and staff. "
Ilana 2-night trip
Posted 3 days ago
On The River Inn

Find out more about Chester

Chester B&B information

Number of reviews
2,685
Accommodation
34 B&B
Lowest Price
RM592
Highest Price
RM1,311

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. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. You might also consider a trip to sites such as Okemo Mountain Resort or Stratton Mountain Resort 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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