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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured B&B in Chester and around

Our top choices for Chester bed & breakfast

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (373)
"After working an entire weekend with festivities in the area checking into here for some much needed rest was the best decision we made very comfortable very nice and very clean "
Bromley View Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (226)
"Great stay! "
The Jackson
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (251)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
The price is €140
includes taxes & fees
1 Sept - 2 Sept
The Inn at Manchester
The Inn at Ormsby Hill
Front of property

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (133)
"Lovely place to stay Jack and Maryann excellent hosts"
The price is €188
includes taxes & fees
24 Aug - 25 Aug
The Inn at Ormsby Hill
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (58)
"I liked that it was right on the scenic route"
Deerfield Valley Inn
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (105)
"Lisa was amazing, super kind and helpful. The rooms were clean and given attention each day. We really enjoyed our stay and will be back next time we are in Vermont. "
Blue Gentian Lodge at Magic Mountain
The Vesper
Economy Room

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (28)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is €159
includes taxes & fees
24 Aug - 25 Aug
The Vesper
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (315)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
The price is €149
includes taxes & fees
31 Aug - 1 Sept
Colonel Williams Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (92)
"Sweet place to stay"
The price is €188
includes taxes & fees
25 Aug - 26 Aug
Stone Hearth Inn and Eatery
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Owners are warm and welcoming. Home is charming and well decorated, breakfast excellent. "
The Buckmaster Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (39)
"Superb stay in all ways!"
The price is €188
includes taxes & fees
28 Aug - 29 Aug
Stay At Jimmy's
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (50)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is €278
includes taxes & fees
26 Aug - 27 Aug
Inn on Putney Road
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
Harvest Barn Inn
Woodbridge Inn
Front of property – evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
The price is €416
includes taxes & fees
21 Sept - 22 Sept
Woodbridge Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is €194
includes taxes & fees
28 Aug - 29 Aug
Deerhill Inn
Windham Hill Inn
Mountain view

Windham Hill Inn

4.0 star property
8.4 out of 10, Very good, (36)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
The price is €177
includes taxes & fees
26 Aug - 27 Aug
Windham Hill Inn
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is €191
includes taxes & fees
27 Aug - 28 Aug
The One Cat B&B
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is €165
includes taxes & fees
21 Sept - 22 Sept
The Carriage Barn Inn
Big Bears Lodge
Garden

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"So close to Mount snow it’s a great place to stay "
The price is €157
includes taxes & fees
27 Aug - 28 Aug
Big Bears Lodge
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is €280
includes taxes & fees
27 Aug - 28 Aug
Chesterfield 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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"."
Murray 1-night trip
Posted 2 days ago
The Shire Woodstock

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?
Take a look at this B&B in the surrounding area: 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 Plummer's Sugar House 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.