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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

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

The Jackson
Exterior

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (209)
"The beds are extremely comfortable. The availability of ice is a nice feature. The flavored coffee machine was a nice surprise. Great recommendations from David. We will be back"
The price is SAR 791
SAR 871 total
includes taxes & fees
15 Apr - 16 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 SAR 377
SAR 414 total
includes taxes & fees
15 Apr - 16 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 SAR 626
SAR 689 total
includes taxes & fees
15 Apr - 16 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 SAR 380
SAR 418 total
includes taxes & fees
15 Apr - 16 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 SAR 632
SAR 695 total
includes taxes & fees
15 Apr - 16 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 SAR 582
SAR 640 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, (303)
"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 SAR 503
SAR 548 total
includes taxes & fees
15 Apr - 16 Apr
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (49)
"Nice quiet bed and breakfast. Staff was great. Walking distance to three restaurants. "
The price is SAR 319
SAR 454 total
includes taxes & fees
15 Apr - 16 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 SAR 770
SAR 847 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 SAR 747
SAR 822 total
includes taxes & fees
15 Apr - 16 Apr
Stay At Jimmy's
Windham Hill Inn
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 SAR 680
SAR 741 total
includes taxes & fees
28 Apr - 29 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 SAR 638
SAR 693 total
includes taxes & fees
5 May - 6 May
The Carriage Barn Inn
Harvest Barn Inn
Exterior

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 SAR 591
SAR 645 total
includes taxes & fees
17 Apr - 18 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 SAR 1,245
SAR 1,357 total
includes taxes & fees
15 Apr - 16 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 SAR 937
SAR 1,031 total
includes taxes & fees
15 Apr - 16 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 SAR 634
SAR 698 total
includes taxes & fees
15 Apr - 16 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 SAR 372
SAR 626 total
includes taxes & fees
15 Apr - 16 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
Garden

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
Front of property

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
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 SAR 760
SAR 2,388 total
includes taxes & fees
15 Apr - 16 Apr
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
Cozy Hideaway near Ludlow/Okemo. 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. Honeymoon Suite with Jacuzzi Tub in Historic Inn: 0.3 mi (0.4 km) from the downtown core. Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!: 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.