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Check prices for these dates

Next weekend
Sep 12 - Sep 14
In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2

B&B in Chester

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (378)
"Small rustic motel with lounge near Bromley winhall etc best prices around and clean overall. Nice staff decent breakfast "
Bromley View Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (228)
"Great stay! "
The Jackson
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (252)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
The price is ￥21,985
￥24,185 total
includes taxes & fees
Sep 9 - Sep 10
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, (136)
"Lovely place to stay Jack and Maryann excellent hosts"
The price is ￥25,261
￥27,787 total
includes taxes & fees
Sep 8 - Sep 9
The Inn at Ormsby Hill
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"We had a lovely time staying here. "
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, (106)
"Quaintly decorated. Lisa and Ken were very good hosts. Not a modern high tech property, but very homey and welcoming. "
The price is ￥28,284
￥31,112 total
includes taxes & fees
Sep 29 - Sep 30
Blue Gentian Lodge at Magic Mountain
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (30)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is ￥24,496
￥26,946 total
includes taxes & fees
Sep 7 - Sep 8
The Vesper
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (318)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
The price is ￥21,919
￥24,111 total
includes taxes & fees
Sep 9 - Sep 10
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, (95)
"Sweet place to stay"
The price is ￥32,259
￥35,163 total
includes taxes & fees
Sep 18 - Sep 19
Stone Hearth Inn and Eatery
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (62)
"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, (42)
"Superb stay in all ways!"
The price is ￥36,864
￥40,550 total
includes taxes & fees
Sep 8 - Sep 9
Stay At Jimmy's
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (53)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
The price is ￥43,636
￥48,001 total
includes taxes & fees
Sep 8 - Sep 9
Inn on Putney Road
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (225)
"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 ￥65,299
￥71,829 total
includes taxes & fees
Sep 16 - Sep 17
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 ￥28,000
￥30,800 total
includes taxes & fees
Sep 14 - Sep 15
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 ￥26,938
￥29,363 total
includes taxes & fees
Sep 8 - Sep 9
Windham Hill Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
The price is ￥26,225
￥28,454 total
includes taxes & fees
Sep 9 - Sep 10
The Carriage Barn 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 ￥42,312
￥46,543 total
includes taxes & fees
Sep 14 - Sep 15
The One Cat B&B
Big Bears Lodge
Garden

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (180)
"So close to Mount snow it’s a great place to stay "
The price is ￥24,687
￥27,156 total
includes taxes & fees
Sep 30 - Oct 1
Big Bears Lodge
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is ￥44,707
￥48,508 total
includes taxes & fees
Sep 7 - Sep 8
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 Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"Historical Landmark. The building is full of history. The service and amenities are wonderful especially considering the history of the building. Beautiful place to stay, relax, and unwind. Mountain views are spectacular. Restaurants are wonderful. Everything is convenient. Staff are friendly and welcoming. I am very happy and would recommend this place to anyone. "
Janine Louise 4-night trip
Posted 7 days ago
The Equinox Golf Resort & Spa

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
Accommodation
52 B&B
Lowest Price
￥21,919
Highest Price
￥65,299

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Searching for B&Bs in Chester?
If you're looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to mingle with other guests, and hearty breakfasts, B&Bs provide a unique setting.
What are the top B&Bs in Chester?
Check out this B&B in the surrounding area: Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the downtown core. Enjoy the unique décor and fireplace in the lobby.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 5 B&Bs for your stay in Chester.
What's the best time of year to stay at a B&B in Chester?
When you're dreaming of a escape to Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you'll be sure to enjoy Chester for its coffeehouses and restaurants. If you're looking to find something to do during your travels, you might consider checking out DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites like 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 center. Otherwise, look 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, you may want to rent a car for your trip.