Bennington B&B: Best 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

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10

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

8 Sept - 9 Sept

5. Victorian mansions Coach Room with Breakfast

Bennington

6. North Shire Lodge

Manchester Center

Jesse

includes taxes & fees

17 Aug - 18 Aug

7. The Inn at Ormsby Hill

Manchester Center

Victoria

includes taxes & fees

18 Aug - 19 Aug

8. Room 1, peaceful retreat in Manchester - King bed

Manchester

Ivy B.

includes taxes & fees

1 Sept - 2 Sept

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Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"The staff was great and welcoming. The room was comfortable and clean. The shower was strong and wonderful. The hotel was walking distance to pubs and restaurants. Overall a great night."

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."

Lake life at Woodford Cottage

10/10 Excellent

"We were 4 nurses from Maine in Bennington volunteering at the annual RAM clinic. We put in long hours and were so grateful to have a clean, comfortable, safe place to lay our heads down at night. A dip in the pond after clinic was a refreshing treat! House was clean, well supplied and well stocked. Hosts were responsive and welcoming. 10/10 would recommend!"

Mountain Sanctuary Dome Rustic Solitude 5BR

10/10 Excellent

"We entered the house in awe. It has inspiring architecture, thriving house plants, great set of games and a cute bathtub with a gorgeous view. Walls are paper thin, so we had to be careful with noise. It's located in the idyllic hill of a mountain. A beautiful swimming hole nearby, and scenic views all around."

Find out more about Bennington

Bennington B&B information

Number of reviews	1,995
Accommodation	26 B&B
Lowest Price	€73
Highest Price	€448

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 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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