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Our top choices for Chester bed & breakfast

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 AU$428
includes taxes & fees
13 Jan - 14 Jan
Stone Hearth Inn and Eatery

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (411 reviews)
"Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!"
United States
Nichole
Bromley View Inn

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

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

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 AU$205
includes taxes & fees
13 Jan - 14 Jan
The Carriage Barn Inn

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 AU$249
includes taxes & fees
13 Jan - 14 Jan
Colonel Williams Inn

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 AU$222
includes taxes & fees
15 Jan - 16 Jan
The One Cat B&B

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (284 reviews)
"Charming bed and breakfast found on a whim. Captures New England charm and the owners are so nice and hospitable. Really liked the bar as well to mingle with locals. Will definitely be returning again!"
United States
Amy
The price is AU$271
includes taxes & fees
13 Jan - 14 Jan
The Inn at Manchester

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

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 AU$274
includes taxes & fees
13 Jan - 14 Jan
Blue Gentian Lodge at Magic Mountain

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 AU$386
includes taxes & fees
13 Jan - 14 Jan
Inn on Putney Road

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 AU$360
includes taxes & fees
13 Jan - 14 Jan
The Inn at Ormsby Hill

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 AU$410
includes taxes & fees
13 Jan - 14 Jan
Stay At Jimmy's

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 AU$265
includes taxes & fees
13 Jan - 14 Jan
The Vesper

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

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 AU$302
includes taxes & fees
13 Jan - 14 Jan
Windham Hill Inn

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 AU$293
includes taxes & fees
13 Jan - 14 Jan
Big Bears Lodge

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1 review)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
The price is AU$199
includes taxes & fees
14 Jan - 15 Jan
Room 7 - family room sleeps 4

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 AU$499
includes taxes & fees
18 Jan - 19 Jan
Chesterfield Inn

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is AU$449
includes taxes & fees
13 Jan - 14 Jan
Deer Brook Inn
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

Find out more about Chester

Chester B&B information

Number of reviews
2,643
Accommodation
62 B&B
Lowest Price
AU$199
Highest Price
AU$499

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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