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

Our top choices for Bennington bed & breakfast

Library

1. South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (128 reviews)
"Staff was great."
United States
Jan
The price is ฿7,009
฿8,004 total
includes taxes & fees
15 Aug - 16 Aug
South Shire
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, iron/ironing board, free WiFi, 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 ฿8,545
฿9,314 total
includes taxes & fees
5 Aug - 6 Aug
The Four Chimneys Inn
Lounge

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (455 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 ฿2,557
฿2,812 total
includes taxes & fees
10 Aug - 11 Aug
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, (359 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is ฿5,567
฿7,043 total
includes taxes & fees
25 Aug - 26 Aug
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 ฿6,306
฿6,937 total
includes taxes & fees
17 Aug - 18 Aug
North Shire Lodge
Front of property – evening/night

6. 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 ฿8,994
฿9,894 total
includes taxes & fees
18 Aug - 19 Aug
The Inn at Ormsby Hill
Outdoor pool, pool loungers

7. 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 ฿5,565
฿13,589 total
includes taxes & fees
17 Aug - 18 Aug
Hill Farm Inn
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 ฿5,266
฿5,793 total
includes taxes & fees
9 Aug - 10 Aug
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
"Very nice rooms , so clean & comfortable, beds & linens excellent"
Judith 1-night trip
Posted 4 hours ago
The Manchester View

Find out more about Bennington

Bennington B&B information

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 B&B
Lowest Price
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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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