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B&B in Bennington

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

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (280)
"Great establishment "
United States
Brenda
The price is AED 606
AED 667 total
includes taxes & fees
4 Jan - 5 January 2026
The Inn at Manchester

The Four Chimneys Inn

4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn

The Inn at Ormsby Hill

3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 731
AED 804 total
includes taxes & fees
10 Dec - 11 Dec
The Inn at Ormsby Hill

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (173)
"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 625
AED 1,507 total
includes taxes & fees
4 Jan - 5 January 2026
Hill Farm Inn

Alpine 5, cozy Vermont retreat

Manchester
The price is AED 251
AED 460 total
includes taxes & fees
9 Dec - 10 Dec
Alpine 5, cozy Vermont retreat

Room 7 - family room sleeps 4

Manchester
The price is AED 251
AED 460 total
includes taxes & fees
9 Dec - 10 Dec
Room 7 - family room sleeps 4

Zen 10, relax and retreat in the heart of Vermont

Manchester
10.0 out of 10, Exceptional, (1)
"Very nice and relaxing location"
United States
Jennifer C.
The price is AED 251
AED 460 total
includes taxes & fees
10 Dec - 11 Dec
Zen 10, relax and retreat in the heart of Vermont

Oceans 8 minutes to Manchester Vermont

Manchester
The price is AED 251
AED 460 total
includes taxes & fees
10 Dec - 11 Dec
Oceans 8 minutes to Manchester Vermont

Cloud 9 family double sleeps 4

Manchester
The price is AED 266
AED 477 total
includes taxes & fees
16 Dec - 17 Dec
Cloud 9 family double sleeps 4

Room 4 - Prickly Pear double room

Manchester
The price is AED 251
AED 460 total
includes taxes & fees
9 Dec - 10 Dec
Room 4 - Prickly Pear double room

6 Bam Boo Cozy escape in the heart of Vermont

Manchester
The price is AED 251
AED 460 total
includes taxes & fees
9 Dec - 10 Dec
6 Bam Boo Cozy escape in the heart of Vermont

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 532
AED 585 total
includes taxes & fees
9 Dec - 10 Dec
Colonel Williams Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"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 750
AED 793 total
includes taxes & fees
8 Jan - 9 January 2026
Harbour House Inn

The Wilmington Inn

3.5 star property
Wilmington
10.0 out of 10, Exceptional, (195)
"Relaxing stay with great hiking nearby"
United States
Charlotte
The price is AED 587
AED 665 total
includes taxes & fees
9 Dec - 10 Dec
The Wilmington Inn

The Nutmeg

3.5 star property
Wilmington
9.4 out of 10, Exceptional, (414)
"This was a beautiful quaint property with delightful and attentive staff. The French toast breakfast was amazing! "
United States
John
The price is AED 605
AED 665 total
includes taxes & fees
8 Jan - 9 January 2026
The Nutmeg

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 706
AED 769 total
includes taxes & fees
9 Dec - 10 Dec
Stone Hearth Inn and Eatery

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
9.0 out of 10, Wonderful, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is AED 638
AED 713 total
includes taxes & fees
9 Dec - 10 Dec
The Trail in Adams - Berkshires’ Art Hotel

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 694
AED 757 total
includes taxes & fees
9 Dec - 10 Dec
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

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 is a B&B that travelers enjoy in Bennington: The Four Chimneys Inn: 11 rooms. Enjoy the free full breakfast and unique décor.
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.