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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Bennington

Lounge
Bromley View Inn
Bromley View Inn
3.5 star property
9.0 out of 10, Wonderful, (395)
"Great place and close to everything "
United States
Debra
Bromley View Inn
Front of property
The Inn at Ormsby Hill
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, (143)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 657
AED 723 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Ormsby Hill
Property grounds
The Inn at Manchester
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (273)
"Beautiful area, great staff"
United States
Matthew
The price is AED 545
AED 600 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Manchester
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn
The Four Chimneys Inn
4.0 star property
9.4 out of 10, Exceptional, (280)
"Great stay!"
United States
Alan
The Four Chimneys Inn
Standard Room, 1 King Bed, Mountain View | Mountain view
North Shire Lodge
North Shire Lodge
3.0 star property
9.4 out of 10, Exceptional, (155)
"Loved our stay at North Shire Lodge.."
United States
Mary
The price is AED 650
AED 716 total
includes taxes & fees
26 Oct - 27 Oct
North Shire Lodge
Front of property
Hill Farm Inn
Hill Farm Inn
4.0 star property
9.6 out of 10, Exceptional, (170)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
The price is AED 856
AED 1,760 total
includes taxes & fees
26 Oct - 27 Oct
Hill Farm Inn
TV
The Nutmeg
The Nutmeg
3.5 star property
9.4 out of 10, Exceptional, (410)
"This was a beautiful quaint property with delightful and attentive staff. The French toast breakfast was amazing! "
United States
John
The price is AED 612
AED 673 total
includes taxes & fees
28 Oct - 29 Oct
The Nutmeg
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (336)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 579
AED 636 total
includes taxes & fees
3 Nov - 4 Nov
Colonel Williams Inn
Dining
Four Columns Inn
Four Columns Inn
3.0 star property
9.6 out of 10, Exceptional, (8)
"Lovely staff, amazing ambiance!"
United States
Julie
Four Columns Inn
Kayaking
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
2.5 star property
9.2 out of 10, Wonderful, (110)
"Lovely pleasant stay. "
United States
Heather
The price is AED 644
AED 709 total
includes taxes & fees
25 Oct - 26 Oct
Blue Gentian Lodge at Magic Mountain
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (102)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 737
AED 803 total
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery
Porch
The Wilmington Inn
The Wilmington Inn
3.5 star property
10.0 out of 10, Exceptional, (191)
"Breakfast great, staff accommodating, Charlie and crew, made you feel like going to grandmas!"
United States
Robert
The price is AED 816
AED 924 total
includes taxes & fees
10 Nov - 11 Nov
The Wilmington Inn
Garden
Big Bears Lodge
Big Bears Lodge
3.0 star property
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is AED 612
AED 674 total
includes taxes & fees
27 Oct - 28 Oct
Big Bears Lodge
Front of property
UU Rowe Camp and Conference Center
UU Rowe Camp and Conference Center
2.0 star property
The price is AED 547
AED 578 total
includes taxes & fees
1 Nov - 2 Nov
UU Rowe Camp and Conference Center
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (138)
"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "
United States
Jonathan
The price is AED 638
AED 713 total
includes taxes & fees
27 Oct - 28 Oct
The Trail in Adams - Berkshires’ Art Hotel
Exterior
Harbour House Inn
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AED 963
AED 1,018 total
includes taxes & fees
29 Oct - 30 Oct
Harbour House Inn
Exterior
Deerfield Valley Inn
Deerfield Valley Inn
3.0 star property
9.6 out of 10, Exceptional, (76)
"Very private, very quiet, pet friendly, great staff"
United States
Blendell
Deerfield Valley Inn
Mountain view
Windham Hill Inn
Windham Hill Inn
4.0 star property
8.4 out of 10, Very Good, (36)
"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 666
AED 726 total
includes taxes & fees
28 Oct - 29 Oct
Windham Hill Inn
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!
Room in Historic Inn! 20 Minutes to Okemo!
9.2 out of 10, Wonderful, (17)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is AED 364
AED 613 total
includes taxes & fees
2 Nov - 3 Nov
Room in Historic Inn! 20 Minutes to Okemo!
Exterior
The Engel House
The Engel House
3.0 star property
9.2 out of 10, Wonderful, (15)
"The perfect Vermont Bed and Breakfast. "
United States
Lee
The Engel House
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 Bennington Hotel Reviews

Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

6/10 Okay
"Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 PM the next day"
Michael 5-night trip
Posted 3 days ago
Bennington Gem w/ Smart TV Near Historic District!

Frequently asked questions

Searching for B&Bs in Bennington?
If you're looking for something a little different than the traditional hotel experience, a bed and breakfast could be a great option for your getaway. If you want to lose yourself exploring fascinating exhibits, you might consider stopping by Bennington Museum and Robert Frost Stone House Museum while you're in town.
Are you thinking about B&Bs over traditional hotel rooms?
B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook, the small details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Bennington?
Below are some well-liked B&Bs in the area: The Four Chimneys Inn: 11 rooms. 0.2 mi (0.3 km) from the heart of Bennington. Enjoy the free full breakfast and unique décor. Big Bears Lodge: 24 rooms. 17.5 mi (28.2 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. The Nutmeg: 14 rooms. Located 16.7 mi (26.9 km) from the core of Bennington. Enjoy the free cooked breakfast and outdoor pool.
When is the best time to book my B&B in Bennington?
When you're planning your escape to Bennington, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.
What is there to do in Bennington?
If you're looking for some things to do on your trip, travelers enjoy Bennington for its skiing and hiking. If you're looking for some activities to entertain you on your trip, consider visiting Harmon Hill and Prospect Mountain Nordic Ski Center. You might put Old First Congregational Church and Bennington Museum on your list if you want to see more of the area.
How can I get to and around Bennington?
Mapping out your trip in and around Bennington is easy with these transportation options. Fly into Albany Intl. Airport (ALB), which is located 31.7 mi (51 km) away from the city center. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.