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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Browse Select Bennington B&B

Lounge
Bromley View Inn
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (391)
"Great place and close to everything "
Bromley View Inn
Property grounds
The Inn at Manchester
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (268)
"Friendly staff and very nice breakfast. "
The price is ฿4,829
฿5,312 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Manchester
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"
The price is ฿5,821
฿6,403 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Ormsby Hill
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)
"Nice and cozy"
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, (154)
"Loved our stay at North Shire Lodge.."
The price is ฿5,759
฿6,335 total
includes taxes & fees
20 Oct - 21 Oct
North Shire Lodge
Exterior
The Ira Allen House
The Ira Allen House
3.5 star property
10.0 out of 10, Exceptional, (204)
"Great two-night stay. "
The price is ฿7,805
฿8,507 total
includes taxes & fees
20 Oct - 21 Oct
The Ira Allen House
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."
The price is ฿7,580
฿15,580 total
includes taxes & fees
26 Oct - 27 Oct
Hill Farm Inn
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (332)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
The price is ฿5,122
฿5,634 total
includes taxes & fees
22 Oct - 23 Oct
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!"
Four Columns Inn
TV
The Nutmeg
The Nutmeg
3.5 star property
9.4 out of 10, Exceptional, (408)
"Room was clean bathroom was modern large clean staff friendly breakfast was awesome gave you 4 choices cofee and tea all day heated pool in season several rooms to just sit and relax in."
The price is ฿5,528
฿6,081 total
includes taxes & fees
28 Oct - 29 Oct
The Nutmeg
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. "
The price is ฿5,821
฿6,403 total
includes taxes & fees
19 Oct - 20 Oct
Blue Gentian Lodge at Magic Mountain
Exterior
Green River Bridge Inn
Green River Bridge Inn
3.0 star property
8.8 out of 10, Excellent, (10)
"Beautiful Inn and property"
The price is ฿7,171
฿7,816 total
includes taxes & fees
2 Nov - 3 Nov
Green River Bridge Inn
Front of property
UU Rowe Camp and Conference Center
UU Rowe Camp and Conference Center
2.0 star property
The price is ฿4,845
฿5,122 total
includes taxes & fees
1 Nov - 2 Nov
UU Rowe Camp and Conference Center
Exterior
Deerfield Valley Inn
Deerfield Valley Inn
3.0 star property
9.6 out of 10, Exceptional, (72)
"We had a lovely time staying here. "
Deerfield Valley Inn
Garden
Big Bears Lodge
Big Bears Lodge
3.0 star property
9.0 out of 10, Wonderful, (182)
"So close to Mount snow it’s a great place to stay "
The price is ฿5,423
฿5,965 total
includes taxes & fees
27 Oct - 28 Oct
Big Bears Lodge
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, (137)
"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. "
The price is ฿5,650
฿6,311 total
includes taxes & fees
22 Oct - 23 Oct
The Trail in Adams - Berkshires’ Art Hotel
Porch
The Wilmington Inn
The Wilmington Inn
3.5 star property
10.0 out of 10, Exceptional, (187)
"Breakfast great, staff accommodating, Charlie and crew, made you feel like going to grandmas!"
The price is ฿7,447
฿8,438 total
includes taxes & fees
10 Nov - 11 Nov
The Wilmington Inn
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!! "
The price is ฿8,530
฿9,016 total
includes taxes & fees
20 Oct - 21 Oct
Harbour House Inn
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (101)
"Good breakfast and dinner options. Great location for hiking."
The price is ฿9,171
฿9,997 total
includes taxes & fees
20 Oct - 21 Oct
Stone Hearth Inn and Eatery
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. "
The price is ฿6,146
฿6,699 total
includes taxes & fees
21 Oct - 22 Oct
Windham Hill 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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Top Bennington Hotel Reviews

South Shire

South Shire

10/10 Excellent
"Quiet, peaceful stay!"
Julie 1-night trip
Posted 3 days ago
South Shire

Find out more about Bennington

Bennington B&B information

Number of reviews
3,050
Accommodation
8 B&B
Lowest Price
฿5,122
Highest Price
฿15,580

Frequently asked questions

Searching for B&Bs in Bennington?
If you're hoping for something a little different than your standard 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 interested in an apartment for your stay?
B&Bs all have a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook, the small details are what make bed and breakfasts a home away from home.
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 decor. Big Bears Lodge: 24 rooms. 17.5 mi (28.2 km) from the city centre. 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.
What's the best time of year 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Bennington are January, March, February and December, with each month seeing an average of 21 cm of snowfall.
What is there to do in Bennington?
If you're looking for some things to do on you trip, travellers 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 should 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?
Planning your excursions in and around Bennington is easier with these transportation options. Fly into Albany, NY (ALB-Albany Intl.), which is located 31.7 mi (51 km) away. Otherwise, look 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.