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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 Aug

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, (120 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is AED 707
AED 771 total
includes taxes & fees
30 Jun - 1 Jul
Stone Hearth Inn and Eatery
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (42 reviews)
"The hot tub was so amazing"
United States
Mark
The price is AED 419
AED 457 total
includes taxes & fees
24 Jun - 25 Jun
Four Columns Inn
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (449 reviews)
"The staff was very friendly and helpful."
Canada
Dumitru Florin
The price is AED 343
AED 378 total
includes taxes & fees
25 Jun - 26 Jun
Bromley View Inn
Kayaking

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (119 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is AED 461
AED 507 total
includes taxes & fees
25 Jun - 26 Jun
Blue Gentian Lodge at Magic Mountain
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is AED 562
AED 610 total
includes taxes & fees
24 Jun - 25 Jun
The Carriage Barn Inn
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (122 reviews)
"We had a wonderful stay! Great location and very friendly inn keeper. Would definitely stay again."
United States
Andrea
The price is AED 282
AED 411 total
includes taxes & fees
24 Jun - 25 Jun
Deerfield Valley Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (266 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
The price is AED 589
AED 641 total
includes taxes & fees
24 Jun - 25 Jun
Harvest Barn Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is AED 528
AED 580 total
includes taxes & fees
30 Jun - 1 Jul
Colonel Williams Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (64 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
The price is AED 643
AED 707 total
includes taxes & fees
28 Jun - 29 Jun
The Vesper
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (288 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is AED 694
AED 764 total
includes taxes & fees
30 Jun - 1 Jul
The Jackson
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (80 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is AED 833
AED 916 total
includes taxes & fees
1 Jul - 2 Jul
The One Cat B&B
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (332 reviews)
"Great cooked to order breakfast, beautiful grounds and perfect central location in town."
United States
Richard
The price is AED 579
AED 636 total
includes taxes & fees
12 Jul - 13 Jul
The Inn at Manchester
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is AED 740
AED 807 total
includes taxes & fees
24 Jun - 25 Jun
Echo Lake Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (2 reviews)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is AED 804
AED 884 total
includes taxes & fees
24 Jun - 25 Jun
Deer Brook Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is AED 915
AED 1,006 total
includes taxes & fees
24 Jun - 25 Jun
Stay At Jimmy's
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is AED 683
AED 744 total
includes taxes & fees
8 Jul - 9 Jul
Windham Hill Inn
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 289
AED 543 total
includes taxes & fees
15 Jul - 16 Jul
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (1 review)
"The room was spotless. The communal guest kitchen is an awesome feature. "
United States
Jacob
The price is AED 324
AED 581 total
includes taxes & fees
20 Jul - 21 Jul
Room 1, peaceful retreat in Manchester - King bed
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (214 reviews)
"Place is great and location as well, 5 minutes from Mount Snow."
United States
Matheus
The price is AED 634
AED 697 total
includes taxes & fees
24 Jun - 25 Jun
Big Bears Lodge
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, (165 reviews)
"This Inn is lovely and our favorite place to stay when we travel to Vermont. The breakfast is amazing!"
United States
Donna
The price is AED 988
AED 1,087 total
includes taxes & fees
24 Jun - 25 Jun
The Inn at Ormsby Hill
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 Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good
"Would have liked to use the hot tub but it was inconvenient to our room"
Wendy 1-night trip
Posted 4 hours ago
The Palmer House Resort, an Ascend Collection Hotel

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?
Here are some well-liked B&Bs in the 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 décor. Bromley View Inn: 16 rooms. Located 17.8 mi (28.6 km) from the core of Chester. 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 My Minds Design or Vermont Country Store 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.

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