Bennington B&B: Find a Bed and Breakfast 2026

Q: What are the top B&Bs in Bennington?

Here are some B&Bs to look at in Bennington: South Shire : 9 rooms. Enjoy the massage services and bar/lounge. The Four Chimneys Inn : 11 rooms. Enjoy the free full breakfast and unique decor.

A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

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Our top choices for Bennington bed & breakfast

A room with wooden paneling, a piano, a chair, and a door leading to another room.

1. South Shire

Bennington

Jorge

includes taxes & fees

26 Oct - 27 Oct

A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

2. North Shire Lodge

Manchester Center

Jesse

includes taxes & fees

28 Sept - 29 Sept

A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

3. The Inn at Manchester

Manchester Village Historic District

Reagan

includes taxes & fees

25 Oct - 26 Oct

A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

4. The Inn at Ormsby Hill

Manchester Center

Victoria

includes taxes & fees

27 Sept - 28 Sept

A swimming pool with a view of a barn and mountains in the background.

5. Hill Farm Inn

Arlington

Jennifer

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, dresser, TV, and a chair.

6. Doveberry Inn

West Dover

Veronica

includes taxes & fees

27 Oct - 28 Oct

A large white building with a stone wall and a lawn covered in fallen leaves.

7. Colonel Williams Inn

Brattleboro

Robert

includes taxes & fees

30 Sept - 1 Oct

A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

8. Deerfield Valley Inn

West Dover

Patrick

includes taxes & fees

30 Sept - 1 Oct

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Top Bennington Hotel Reviews

Bromley View Inn

10/10 Excellent

"Very pet friendly with very friendly staff that even gave our dogs free toys"

The Manchester View

10/10 Excellent

"Property has been renovated-it is very clean and modern. Nice simple breakfast served. Housekeeping didn’t show the 2nd day of our stay. ( we hunted them down for towels before getting ready for a wedding. They offered to come then- but it was too late in the day) Great views and quite location."

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"I travel for work and had the opportunity to stay at this property for 2 months. This is a great lodge in a lovely part of the country. The friendly staff will go out of their way to accomodate guests if at all possible. This is a modernized lodge type property in a picturesque setting. There are room options that include a sauna in the room. There is also a flash heater type of water heater that provides almost instant and endless hot water on demand. The breakfast offerings include the personal waffle iron kit and all you can eat of it. I never had even the slightest issue with cleanliness and the staff strives to make your stay enjoyable. I don’t know how this property rates with others, but I give it a solid 5 out of 5 stars."

Find out more about Bennington

Bennington B&B information

Number of reviews	1,585
Accommodation	8 B&B
Lowest Price	S$155
Highest Price	S$704

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?

Here are some B&Bs to look at in Bennington: South Shire: 9 rooms. Enjoy the massage services and bar/lounge. The Four Chimneys Inn: 11 rooms. Enjoy the free full breakfast and unique decor.

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 Bennington Museum and Bennington Center for the Arts 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.

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