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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

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, (109 reviews)
"So great all around!"
United States
Janet
The price is RM1,142
RM1,245 total
includes taxes & fees
19 Jan - 20 Jan
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (412 reviews)
"Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!"
United States
Nichole
Bromley View Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (342 reviews)
"Absolutely stunning bed and breakfast! The room and facilities were clean and welcoming. We really enjoyed the decorations and details of the house. The breakfast was delicious! Will definitely be coming back next time we are in town for ski! Highly recommended staying at Colonel Williams! "
United States
Ekaterina
The price is RM638
RM702 total
includes taxes & fees
18 Jan - 19 Jan
Colonel Williams 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, (245 reviews)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn 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 RM516
RM560 total
includes taxes & fees
20 Jan - 21 Jan
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, (284 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is RM668
RM735 total
includes taxes & fees
19 Jan - 20 Jan
The Inn at Manchester
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261 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
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 RM1,245
RM1,351 total
includes taxes & fees
18 Jan - 19 Jan
Chesterfield Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56 reviews)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is RM950
RM1,045 total
includes taxes & fees
19 Jan - 20 Jan
Inn on Putney Road
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, (151 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is RM887
RM976 total
includes taxes & fees
19 Jan - 20 Jan
The Inn at Ormsby Hill
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (186 reviews)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is RM722
RM794 total
includes taxes & fees
19 Jan - 20 Jan
Big Bears Lodge
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 RM547
RM601 total
includes taxes & fees
20 Jan - 21 Jan
The One Cat B&B
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 RM725
RM797 total
includes taxes & fees
21 Jan - 22 Jan
Blue Gentian Lodge at Magic Mountain
Exterior

Deerhill Inn

Deerhill Inn
3.5 star property
West Dover
9.6 out of 10, Exceptional, (226 reviews)
"Super clean and well appointed room. Lovely greeting "
United States
Kathleen
The price is RM830
RM913 total
includes taxes & fees
19 Jan - 20 Jan
Deerhill Inn
Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very good, (38 reviews)
"Did not use"
United States
Douglas
The price is RM765
RM834 total
includes taxes & fees
19 Jan - 20 Jan
Windham Hill Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46 reviews)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is RM1,008
RM1,109 total
includes taxes & fees
20 Jan - 21 Jan
Stay At Jimmy's
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (95 reviews)
"Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel."
Canada
Shane
Deerfield Valley Inn
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98 reviews)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
The price is RM1,180
RM1,287 total
includes taxes & fees
20 Jan - 21 Jan
Echo Lake Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is RM752
RM827 total
includes taxes & fees
20 Jan - 21 Jan
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

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

10/10 Excellent
"Ski on skis off fantastic. Ski valet right on it "
John 3-night trip
Posted 4 days ago
Mount Snow Grand Summit Resort

Find out more about Chester

Chester B&B information

Number of reviews
2,874
Accommodation
34 B&B
Lowest Price
RM560
Highest Price
RM1,351

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 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. 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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