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

Search Bed and Breakfasts in Bennington

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sept - 13 Sept
In two months
9 Oct - 11 Oct

Our top choices for Bennington bed & breakfast

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, iron/ironing board, free WiFi, individually decorated

1. 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 ₹24,353
₹26,545 total
includes taxes & fees
18 Aug - 19 Aug
The Four Chimneys Inn
Library

2. 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 ₹19,749
₹22,565 total
includes taxes & fees
28 Aug - 29 Aug
South Shire
Lounge

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (458 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 ₹7,286
₹8,014 total
includes taxes & fees
16 Aug - 17 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, (365 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is ₹13,294
₹16,818 total
includes taxes & fees
7 Sept - 8 Sept
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 ₹18,082
₹19,891 total
includes taxes & fees
18 Aug - 19 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, (171 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is ₹25,635
₹28,198 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, (179 reviews)
"Our favorite place to stay!!"
United States
Jennifer
The price is ₹15,860
₹38,730 total
includes taxes & fees
18 Aug - 19 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 ₹15,009
₹16,511 total
includes taxes & fees
23 Aug - 24 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Bennington Motor Inn

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."
schuyler 1-night trip
Posted 12 hours ago
Bennington Motor Inn

Find out more about Bennington

Bennington B&B information

Number of reviews
3,063
Accommodation
8 B&B
Lowest Price
₹8,014
Highest Price
₹38,730

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.

Explore a world of travel with Expedia