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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 53 B&B in Chester with updated reviews, rates, and availability.

The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (208)
"Beautiful property with wonderful attention to detail and warm, friendly staff — really enjoyed our stay! Woodstock is a charming town and The Jackson staff offered great local recommendations in addition to providing comfortable lodging with thoughtful amenities, delicious breakfast and pretty views. Thank you to Dave and team — highly recommend!"
The price is AED 729
AED 802 total
includes taxes & fees
12 Apr - 13 Apr
The Jackson
Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (340)
"Cozy inn, kids liked playing pool in the common area. Nice gas fireplace and Tv. Great breakfast. Close to several ski areas. Free coffee all day!"
The price is AED 368
AED 405 total
includes taxes & fees
9 Apr - 10 Apr
Bromley View Inn
Big Bears Lodge
Outdoor spa tub

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"It was very close to the ski resort. "
The price is AED 612
AED 674 total
includes taxes & fees
11 Apr - 12 Apr
Big Bears Lodge
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.8 out of 10, Exceptional, (16)
"Lovely"
The price is AED 372
AED 409 total
includes taxes & fees
16 Apr - 17 Apr
The Vesper
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (118)
"Great inn. Very warm and friendly. Perfect for a getaway. Close proximity to town and restaurants. "
The price is AED 618
AED 680 total
includes taxes & fees
9 Apr - 10 Apr
The Inn at Ormsby Hill
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (236)
"Wonderful B & B in Manchester! The staff was so kind and accommodating, the room clean and well appointed and the entire property warm and inviting. Highly recommend. "
The price is AED 569
AED 626 total
includes taxes & fees
4 May - 5 May
The Inn at Manchester
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (302)
"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 550
AED 599 total
includes taxes & fees
9 Apr - 10 Apr
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (48)
"Accommodating staff. Nice old Inn convenient to Mt. Snow and restaurants. Had a great stay. Would stay here again."
The price is AED 312
AED 444 total
includes taxes & fees
9 Apr - 10 Apr
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Amazing property! Absolutely will return again"
The price is AED 753
AED 828 total
includes taxes & fees
17 Apr - 18 Apr
Deerhill Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (29)
"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
9 Apr - 10 Apr
Stay At Jimmy's
Windham Hill Inn
Romantic Room, 1 King Bed | Mountain view

Windham Hill Inn

3.0 star property
8.4 out of 10, Very Good, (33)
"The rustic charm of a beautifully renovated New England barn, with spacious rooms that provide quiet solitude and comfortable furnishings, wall to wall! The king size bed, the oversized bathroom with a giant jetted tub beneath a skylight…SO INCREDIBLY PEACEFUL!! And outdoors there are numerous trails and Adirondack chairs placed at scenic spots to take in the beauty of the land in front of you and to enjoy the star filled wide-open sky above at night, which we did and thoroughly enjoyed! We...
The price is AED 665
AED 725 total
includes taxes & fees
22 Apr - 23 Apr
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, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is AED 573
AED 621 total
includes taxes & fees
5 May - 6 May
The Carriage Barn Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (209)
"Great accomodations. Kaelan & Blessing were wonderful hosts and very accommodating to my requests. The breakfasts were excellent - well-balanced, nutritious, and filling. A quaint, inn in a quiet location with a nice view. A very nice weekend stay at a very reasonable price. Would highly recommend, and would certainly stay there again."
The price is AED 579
AED 631 total
includes taxes & fees
10 Apr - 11 Apr
Harvest Barn Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (89)
"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 1,218
AED 1,327 total
includes taxes & fees
9 Apr - 10 Apr
Stone Hearth Inn and Eatery
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
Echo Lake Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (45)
"Excellent"
The price is AED 862
AED 948 total
includes taxes & fees
9 Apr - 10 Apr
Inn on Putney Road
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (98)
"Amazing "
The price is AED 621
AED 683 total
includes taxes & fees
9 Apr - 10 Apr
Blue Gentian Lodge at Magic Mountain
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"I was enchanted to be staying in a beautiful antique decorated place. And the jacuzzi tub was large, comfortable, and easily accessed by a step."
The price is AED 364
AED 613 total
includes taxes & fees
9 Apr - 10 Apr
Honeymoon Suite with Jacuzzi Tub in Historic Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"I had a great stay at the Buckmaster Inn for ski weekend at Okemo. The house is beautiful with many classic colonial touches throughout. Best of all, Richard and Elizabeth are gracious hosts who go above and beyond to make their guests comfortable. It snowed the last night of my stay and Richard got up extra early to clear the driveway and my car! I will be back whenever I can visit. "
The Buckmaster Inn
Four Columns Inn
Deluxe Room | Living area | 20-inch TV with cable channels

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns 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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Other property types in Chester

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (16)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 744
AED 2,365 total
includes taxes & fees
15 Apr - 16 Apr
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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.

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. Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!: 0.3 mi (0.4 km) from the downtown core. King & Queen Suite in Historic Inn Circa 1780: Situated 0.3 mi (0.4 km) from the heart of Chester. 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 Vermont Country Store or Baltimore Covered Bridge 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.