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
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Bennington bed & breakfast

Library

1. South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (129 reviews)
"Staff was great."
United States
Jan
The price is ₩291,756
₩333,360 total
includes taxes & fees
Aug 11 - Aug 12
South Shire
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, iron/ironing board, WiFi (free), individually decorated

2. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (290 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 ₩363,584
₩396,306 total
includes taxes & fees
Aug 18 - Aug 19
The Four Chimneys Inn
Lounge

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (456 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 ₩108,783
₩119,653 total
includes taxes & fees
Aug 10 - Aug 11
Bromley View Inn
Property grounds

4. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (364 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is ₩196,396
₩248,459 total
includes taxes & fees
Sep 7 - Sep 8
The Inn at Manchester
Exterior

5. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (162 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is ₩267,141
₩293,862 total
includes taxes & fees
Aug 9 - Aug 10
North Shire Lodge
Outdoor pool, sun loungers

6. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (177 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 ₩236,787
₩578,231 total
includes taxes & fees
Aug 10 - Aug 11
Hill Farm Inn
Front of property - evening/night

7. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (169 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is ₩378,714
₩416,585 total
includes taxes & fees
Aug 19 - Aug 20
The Inn at Ormsby Hill
Front of property

8. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is ₩221,738
₩243,911 total
includes taxes & fees
Aug 9 - Aug 10
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Clean, comfortable, great location, friendly staff"
william 1-night trip
Posted 2 hours ago
Hampton Inn and Suites Manchester

Find out more about Bennington

Bennington B&B information

Number of reviews
1,976
Accommodation
8 B&B
Lowest Price
₩119,653
Highest Price
₩578,231

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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