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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

B&B in Chester

The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (216)
"What a lovely place to stay. The couple that manage The Jackson are absolutely wonderful and made our stay fabulous. I would highly recommend staying here with gorgeous surroundings, charming rooms and lovely hospitality."
The Jackson
The Inn at Ormsby Hill
Front of property

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (123)
"Thank you for a wonderful stay!"
The price is AED 694
AED 763 total
includes taxes & fees
17 Jun - 18 Jun
The Inn at Ormsby Hill
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (217)
"Very accommodating and wonderful people! Hoping to return!"
Harvest Barn Inn
Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (349)
"It was nice that they had a pool table in the common area."
Bromley View Inn
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (240)
"Todd gave us the warmest welcome. Breakfast was delicious. Comfortable, cozy, lovely country inn! Staff is terrific!"
The price is AED 643
AED 707 total
includes taxes & fees
17 Jun - 18 Jun
The Inn at Manchester
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (304)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is AED 532
AED 580 total
includes taxes & fees
19 Jun - 20 Jun
Colonel Williams Inn
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (20)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is AED 643
AED 707 total
includes taxes & fees
18 Jun - 19 Jun
The Vesper
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (148)
"The carriage inn has a lot of character. It was very comfortable and easy "
The price is AED 557
AED 604 total
includes taxes & fees
22 Jun - 23 Jun
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 AED 612
AED 674 total
includes taxes & fees
17 Jun - 18 Jun
Big Bears Lodge
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (31)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is AED 731
AED 804 total
includes taxes & fees
17 Jun - 18 Jun
Stay At Jimmy's
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (46)
"The breakfast was excellent and Paul did whatever he could to enhance our stay "
The price is AED 974
AED 1,072 total
includes taxes & fees
17 Jun - 18 Jun
Inn on Putney Road
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (50)
"Overall great spot!"
Deerfield Valley Inn
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Such nice innkeepers! And a bespoke breakfast to boot. I hope I'm back in Brattleboro soon so I can spend another night at the One Cat B&B. Next time I hope to meet the cat."
The price is AED 810
AED 891 total
includes taxes & fees
22 Jun - 23 Jun
The One Cat B&B
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (102)
"Great stay"
The price is AED 1,106
AED 1,200 total
includes taxes & fees
26 Jun - 27 Jun
Chesterfield Inn
Windham Hill Inn
Mountain view

Windham Hill Inn

4.0 star property
8.4 out of 10, Very Good, (34)
"Amazing trip. Beautiful property. Hope to return someday. "
The price is AED 694
AED 757 total
includes taxes & fees
17 Jun - 18 Jun
Windham Hill Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (90)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is AED 682
AED 744 total
includes taxes & fees
15 Jul - 16 Jul
Stone Hearth Inn and Eatery
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is AED 437
AED 736 total
includes taxes & fees
17 Jun - 18 Jun
King & Queen Suite in Historic Inn Circa 1780
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (98)
"A great room close to the slopes; warm and comfortable; breakfast that was included was simple but home cooked and amazing."
The price is AED 474
AED 521 total
includes taxes & fees
17 Jun - 18 Jun
Blue Gentian Lodge at Magic Mountain
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Interior

Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature

10.0 out of 10, Exceptional, (1)
"A warm and inviting host and a cute cozy space to spend a few days. Nice big bedrooms with a fireplace our host supplied wood and we were able to enjoy that. Great location for visiting our son at Dartmouth really close to Woodstock and Quechee!Great stay!"
The price is AED 728
AED 1,141 total
includes taxes & fees
18 Jun - 19 Jun
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Golden Stage Inn B&B
Seasonal outdoor pool

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Very beautiful place and excellent service "
Golden Stage Inn B&B
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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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?
This is a B&B that Expedia travelers like in Chester: Stone Hearth Inn and Eatery: 8 rooms. Enjoy the free buffet breakfast and unique décor.
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 Lowell Lake State Park 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.