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

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Check prices for these dates

Next weekend
Jul 17 - Jul 19
In two weeks
Jul 24 - Jul 26
In one month
Aug 7 - Aug 9
In two months
Sep 4 - Sep 6

Our top choices for Bennington bed & breakfast

Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (450 reviews)
"staff actually treated you like family and not another customer & Clean room & relaxing backyard to watch the sunset & great breakfast"
United States
Josh
The price is P5,228
P5,751 total
includes taxes & fees
Jul 15 - Jul 16
Bromley View Inn
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (346 reviews)
"Great cooked to order breakfast, beautiful grounds and perfect central location in town."
United States
Richard
The price is P9,691
P12,261 total
includes taxes & fees
Jul 15 - Jul 16
The Inn at Manchester
Front of property - evening/night

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (165 reviews)
"This Inn is lovely and our favorite place to stay when we travel to Vermont. The breakfast is amazing!"
United States
Donna
The price is P16,552
P18,208 total
includes taxes & fees
Jul 14 - Jul 15
The Inn at Ormsby Hill
Library

South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (127 reviews)
"Staff was great."
United States
Jan
The price is P12,830
P14,655 total
includes taxes & fees
Jul 19 - Jul 20
South Shire
Exterior

North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (161 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is P11,605
P12,766 total
includes taxes & fees
Jul 14 - Jul 15
North Shire Lodge
Premium bedding, individually decorated, individually furnished

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (289 reviews)
"Peaceful and whimsical stay in a historic inn. The breakfast was delicious (served with the best local maple syrup) and location was a 5 minute drive to the downtown area."
United States
Jeane
The price is P15,725
P17,140 total
includes taxes & fees
Jul 26 - Jul 27
The Four Chimneys Inn
Outdoor pool, sun loungers

Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (176 reviews)
"This is our fourth time staying. We love the inn. Very cozy vibes, restaurant on site is delicious. Very close to Manchester, which has great shops and restaurants."
United States
Jennifer
The price is P16,559
P31,894 total
includes taxes & fees
Jul 12 - Jul 13
Hill Farm Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (356 reviews)
"Great breakfast!"
United States
Billie
The price is P9,691
P10,661 total
includes taxes & fees
Jul 15 - Jul 16
Colonel Williams 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

The Four Chimneys Inn

The Four Chimneys Inn

10/10 Excellent
"We enjoyed our stay."
Robert 1-night trip
Posted less than an hour ago
The Four Chimneys Inn

Find out more about Bennington

Bennington B&B information

Number of reviews
2,070
Accommodation
8 B&B
Lowest Price
P5,751
Highest Price
P31,894

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?
Here are some B&Bs to check out 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 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 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?
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.

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