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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

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, (206)
"Great staff and services. Rooms and toilets are a bit small. "
The price is SAR 744
SAR 819 total
includes taxes & fees
20 Mar - 21 Mar
The Jackson
Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (338)
"This was our 2nd stay at the Bromley View Inn and we can't wait to come back again. The rooms are comfortable and clean but the best part is the common area. We have met lots of other people (mostly skiers) and the environment is great. "
The price is SAR 376
SAR 414 total
includes taxes & fees
30 Mar - 31 Mar
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 625
SAR 688 total
includes taxes & fees
25 Mar - 26 Mar
Big Bears Lodge
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 SAR 591
SAR 644 total
includes taxes & fees
27 Mar - 28 Mar
Colonel Williams Inn
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is SAR 486
SAR 535 total
includes taxes & fees
7 Apr - 8 Apr
The Vesper
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (229)
"Cozy, comfortable. Loved the Inn"
The price is SAR 544
SAR 598 total
includes taxes & fees
30 Mar - 31 Mar
The Inn at Manchester
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (216)
"Never disappoints!"
The price is SAR 769
SAR 846 total
includes taxes & fees
20 Mar - 21 Mar
Deerhill 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 SAR 690
SAR 862 total
includes taxes & fees
20 Mar - 21 Mar
Deerfield Valley Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (28)
"We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was...
The price is SAR 746
SAR 821 total
includes taxes & fees
27 Mar - 28 Mar
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 SAR 679
SAR 740 total
includes taxes & fees
1 Apr - 2 Apr
Windham Hill Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (208)
"Nice and comfortable great breakfast"
The price is SAR 591
SAR 644 total
includes taxes & fees
25 Mar - 26 Mar
Harvest Barn Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (144)
"I was in town for the Harris Hill Ski Jump Challenge in Brattleboro, VT and decided to stay in Keene, NH a town I always wanted to visit. I couldn't have picked a better location. What a lovely place and a brisk 5-minute walk got me into town with a great bakery, running store and restaurants. I'll be back, so much more to do and see. Even got an afternoon of skiing in at Granite Gorge."
The price is SAR 579
SAR 628 total
includes taxes & fees
3 Apr - 4 Apr
The Carriage Barn Inn
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 651
SAR 716 total
includes taxes & fees
26 Mar - 27 Mar
Blue Gentian Lodge at Magic Mountain
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (87)
"The Inn was lovely. My grandchildren were welcomed with open arms ages 8 and 10. They loved our stay and asked for us to take them back. Breakfast specials were delicious and the attached restaurant was as well. We’ll be back!!"
The price is SAR 1,244
SAR 1,355 total
includes taxes & fees
7 Apr - 8 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."
The price is SAR 984
SAR 1,072 total
includes taxes & fees
7 Apr - 8 Apr
Echo Lake Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (44)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is SAR 880
SAR 968 total
includes taxes & fees
20 Mar - 21 Mar
Inn on Putney Road
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (117)
"Great inn. Very warm and friendly. Perfect for a getaway. Close proximity to town and restaurants. "
The price is SAR 532
SAR 585 total
includes taxes & fees
1 Apr - 2 Apr
The Inn at Ormsby Hill
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Interior

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very Good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is SAR 319
SAR 588 total
includes taxes & fees
30 Mar - 31 Mar
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Miscellaneous

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is SAR 1,294
SAR 1,608 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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 Stratton Mountain Resort 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.