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B&B in Chester

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Room was super quiet and clean. "
United States
Ernest
The price is AED 683
AED 744 total
includes taxes & fees
16 Dec - 17 Dec
Stone Hearth Inn and Eatery

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
The price is AED 312
AED 555 total
includes taxes & fees
16 Nov - 17 Nov
Room in Historic Inn! 20 Minutes to Okemo!

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

Chester Depot
9.0 out of 10, Wonderful, (2)
"Yes, wonderful location and stay"
United States
Sharon
The price is AED 327
AED 592 total
includes taxes & fees
25 Nov - 26 Nov
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
The price is AED 511
AED 835 total
includes taxes & fees
25 Nov - 26 Nov
King & Queen Suite in Historic Inn Circa 1780

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
The price is AED 400
AED 654 total
includes taxes & fees
16 Nov - 17 Nov
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (401)
"Overall a decent stay."
United States
Libin
Bromley View Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (10)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
The price is AED 479
AED 522 total
includes taxes & fees
15 Dec - 16 Dec
Four Columns Inn

Harvest Barn Inn

3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (243)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (164)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
The price is AED 604
AED 655 total
includes taxes & fees
1 Dec - 2 Dec
The Carriage Barn Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
The price is AED 578
AED 636 total
includes taxes & fees
20 Nov - 21 Nov
Colonel Williams Inn

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (247)
"The room, the staff, the amenities were what we were hoping for. The Jackson is a great place to stay! "
United States
Frederick
The Jackson

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (84)
"We had a lovely time staying here. "
United States
Jeff
The price is AED 238
AED 362 total
includes taxes & fees
25 Nov - 26 Nov
Deerfield Valley Inn

The Inn at Ormsby Hill

3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (148)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 687
AED 756 total
includes taxes & fees
16 Dec - 17 Dec
The Inn at Ormsby Hill

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
United States
Brandon
The price is AED 659
AED 719 total
includes taxes & fees
26 Nov - 27 Nov
Windham Hill Inn

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (277)
"The staff was so friendly and helpful. Would definitely recommend. "
United States
Christine
The price is AED 606
AED 667 total
includes taxes & fees
16 Nov - 17 Nov
The Inn at Manchester

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
The price is AED 731
AED 804 total
includes taxes & fees
16 Nov - 17 Nov
Stay At Jimmy's

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"We loved our stay! Very welcoming and cozy. The breakfast was delicious. Will definitely come back to stay here again!"
United States
Wiley
The price is AED 909
AED 1,000 total
includes taxes & fees
25 Nov - 26 Nov
The One Cat B&B

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (44)
"The Vesper was a great find in Woodstock VT. Close to downtown to walk to everything. Rooms are spotless and charming. We would definitely stay at the Vesper BnB again."
United States
Kevin
The price is AED 565
AED 621 total
includes taxes & fees
17 Nov - 18 Nov
The Vesper

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is AED 980
AED 1,078 total
includes taxes & fees
16 Nov - 17 Nov
Inn on Putney Road

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The property is conveniently located in close proximity to Mt Snow and local restaurants. The staff is friendly. There's a big screen tv room with fireplace and a small sitting room to read or just converse. Rooms are a little dated but clean. Would stay again."
United States
Jonathan
The price is AED 612
AED 674 total
includes taxes & fees
16 Dec - 17 Dec
Big Bears Lodge
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Top Chester Hotel Reviews

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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 is a B&B that guests like in the surrounding area: 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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.