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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Bennington bed & breakfast

A bookshelf with books and decorative items against a floral wallpaper background.

1. South Shire

South Shire
4.0 star property
Bennington
9.0 out of 10, Wonderful, (141 reviews)
"Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants."
United States
Jeffrey
The price is 4.096.881 ₫
4.746.003 ₫ total
includes taxes & fees
21 Nov - 22 Nov
South Shire
A large, two-story house with a covered porch and multiple chimneys.

2. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.6 out of 10, Exceptional, (291 reviews)
"We enjoyed our stay."
United States
Robert
The price is 5.755.113 ₫
6.273.073 ₫ total
includes taxes & fees
23 Nov - 24 Nov
The Four Chimneys Inn
A cozy room with a fireplace, green sofas, a pool table, and a lamp.

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (503 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
The price is 2.127.414 ₫
2.340.309 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Bromley View Inn
A large, snow-covered house with multiple windows and a well-lit porch.

4. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (401 reviews)
"Great place. Great host!"
United States
Zhihao
The price is 3.582.500 ₫
4.532.183 ₫ total
includes taxes & fees
15 Nov - 16 Nov
The Inn at Manchester
A swimming pool with a view of a barn and mountains in the background.

5. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.8 out of 10, Exceptional, (182 reviews)
"Our favorite place to stay!!"
United States
Jennifer
The price is 6.651.379 ₫
13.028.485 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hill Farm Inn
A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

6. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (165 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is 5.315.967 ₫
5.847.564 ₫ total
includes taxes & fees
7 Nov - 8 Nov
North Shire Lodge
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

7. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (172 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is 5.880.949 ₫
6.469.044 ₫ total
includes taxes & fees
3 Dec - 4 Dec
The Inn at Ormsby Hill
A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

8. Doveberry Inn

Doveberry Inn
3.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
The price is 3.466.935 ₫
3.813.629 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Doveberry Inn
A hotel room with a bed, a desk with a computer, a chair, a lamp, and a window with curtains.

9. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (140 reviews)
"A very quaint, cozy inn set in West Dover, Vermont. We had a small room but it was clean and comfortable. We didn't choose to order breakfast while we were there but it smelled wonderful! Oz, the host, was professional, pleasant, and helpful."
United States
Ted
The price is 1.183.557 ₫
2.009.349 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Deerfield Valley 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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Bennington and related destinations

Stroll through the charming city centre, where the Bennington Museum showcases local art and the famous 'Bennington Flag.' Hike up to the Bennington Battle Monument for panoramic views, then explore the covered bridges and Robert Frost's grave in nearby North Bennington.

See all hotels in Bennington
A mountainous landscape with autumn foliage, a prominent church spire, and a winding road.

Top reviews in Bennington

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
Four Columns Inn

Four Columns Inn

Four Columns Inn
Newfane

8/10 Good

We only had an opportunity to stay one night stay but overall had a very pleasant experience. The room was really nice apart from the wierd location of the television . The bar was "like a real bar " and the lady serving was great ( as was the live entertainment ). Our dining experience has room for improvement although the staff were really nice . Breakfast was "OK" . Good coffee . The owner was extremely friendly and the location and grounds are beautiful . Check in was a little fluffy - I...
United Kingdom
Philip
Reviewed August 3, 2026
Four Columns Inn

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'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 Prospect Mountain Nordic Ski Center and Prospect Mountain Cross-Country Ski Center. You should put Woodford State Park and Green Mountain National Forest 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.