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

Premium bedding, iron/ironing board, free WiFi, individually decorated

1. The Four Chimneys Inn

Bennington

Jeane

includes taxes & fees

18 Aug - 19 Aug

2. South Shire

Bennington

Jan

includes taxes & fees

18 Aug - 19 Aug

3. Bromley View Inn

Bondville

Josh

includes taxes & fees

16 Aug - 17 Aug

4. The Inn at Manchester

Manchester Village Historic District

Lori

includes taxes & fees

7 Sept - 8 Sept

5. North Shire Lodge

Manchester Center

Jesse

includes taxes & fees

16 Aug - 17 Aug

6. The Inn at Ormsby Hill

Manchester Center

Victoria

includes taxes & fees

18 Aug - 19 Aug

7. Hill Farm Inn

Arlington

Jennifer

includes taxes & fees

25 Aug - 26 Aug

8. Colonel Williams Inn

Brattleboro

Robert

includes taxes & fees

13 Aug - 14 Aug

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Top Bennington Hotel Reviews

Bennington Motor Inn

8/10 Good

"It was handy to everywhere in Bennington (which, admittedly is a small town)and was a fine place to stay. Parking was a bit dicey, being on a steep side hill, and the main walkway out front ( a first floor balcony) was tilted a bit away from the building- a drink and I might have been over into the driveway. I would stay there again."

Knotty Pine

8/10 Good

"Staff was very nice and helpful. Rooms were nice but dated. Really not a bad place to stay. The only complaints were that the washing machines were broken so we couldn't do laundry (we're hiking the AT/Long Trail and very dirty clothes) and the breakfast was disappointing (looking forward to a hot breakfast but they only offer a granola bar, fruit cup and juice in a brown bag) but it was ok for us. Another plus is a Wal-mart, Price Chopper, Starbucks, and restaurants very close for resupply and chow time."

Find out more about Bennington

Bennington B&B information

Number of reviews	3,064
Accommodation	8 B&B
Lowest Price	S$108
Highest Price	S$520

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 Harmon Hill and Prospect Mountain Nordic Ski Center. You should put Bennington Museum and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display 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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