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
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

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

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (131 reviews)
"Super charming Victorian home. Perfect spot to disconnect and enjoy a restful stay"
United States
Maria Belinda
The price is P12,818
P14,646 total
includes taxes & fees
Aug 31 - Sep 1
South Shire
A cozy room with a fireplace, green sofas, a pool table, and a lamp.

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (471 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is P4,729
P5,202 total
includes taxes & fees
Aug 30 - Aug 31
Bromley View Inn
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

3. 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 P17,570
P19,151 total
includes taxes & fees
Aug 31 - Sep 1
The Four Chimneys Inn
A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

4. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (373 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is P8,629
P10,916 total
includes taxes & fees
Sep 9 - Sep 10
The Inn at Manchester
A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

5. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (164 reviews)
"Wonderful find in Vermont. The staff provides what you need while maintaining a room for your privacy. Everything is in the vincinity with each access."
United States
Libin K
The price is P11,737
P12,911 total
includes taxes & fees
Aug 30 - Aug 31
North Shire Lodge
A swimming pool with a view of a barn and mountains in the background.

6. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (179 reviews)
"Our favorite place to stay!!"
United States
Jennifer
The price is P18,494
P34,077 total
includes taxes & fees
Aug 30 - Aug 31
Hill Farm Inn
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

7. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (172 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is P26,535
P29,189 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Ormsby Hill

8. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
The price is P9,352
P10,288 total
includes taxes & fees
Aug 30 - Aug 31
Doveberry Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

9. 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 P9,806
P10,787 total
includes taxes & fees
Aug 31 - Sep 1
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 Manchester View

The Manchester View

10/10 Excellent
"Beautiful property, and recently received a significant makeover. Great place to stay."
Jason 1-night trip
Posted 14 hours ago
The Manchester View

Find out more about Bennington

Bennington B&B information

Number of reviews
1,765
Accommodation
8 B&B
Lowest Price
P5,202
Highest Price
P34,077

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 Prospect Mountain Nordic Ski Center and Prospect Mountain Cross-Country 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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