Silk Road covered bridge with trees showing fall colors near Paper Mill Village, Vermont.

Search B&B 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
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

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, (448 reviews)
"The staff was very friendly and helpful."
Canada
Dumitru Florin
The price is AED 312
AED 343 total
includes taxes & fees
23 Jun - 24 Jun
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, (332 reviews)
"Great cooked to order breakfast, beautiful grounds and perfect central location in town."
United States
Richard
The price is AED 579
AED 636 total
includes taxes & fees
15 Jul - 16 Jul
The Inn at Manchester
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 AED 729
AED 834 total
includes taxes & fees
22 Jun - 23 Jun
South Shire
Exterior

North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (159 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is AED 693
AED 762 total
includes taxes & fees
29 Jun - 30 Jun
North Shire Lodge
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 AED 988
AED 1,087 total
includes taxes & fees
22 Jun - 23 Jun
The Inn at Ormsby Hill
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | 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, (284 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 AED 861
AED 938 total
includes taxes & fees
7 Jul - 8 Jul
The Four Chimneys Inn
Exterior

Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (1 review)
"The room was spotless. The communal guest kitchen is an awesome feature. "
United States
Jacob
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
Room 1, peaceful retreat in Manchester - King bed
Exterior

Victorian mansions Coach Room with Breakfast

Victorian mansions Coach Room with Breakfast
Bennington
The price is AED 744
AED 961 total
includes taxes & fees
22 Jun - 23 Jun
Victorian mansions Coach Room with Breakfast
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 AED 988
AED 1,904 total
includes taxes & fees
25 Jun - 26 Jun
Hill Farm Inn
Property grounds

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1 review)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
The price is AED 297
AED 551 total
includes taxes & fees
14 Jul - 15 Jul
Room 7 - family room sleeps 4
Dining

Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Manchester
6.8 out of 10, (3 reviews)
"We had a wonderful stay! The room was very clean and spacious, which made it extremely comfortable and relaxing. Everything was well maintained and exactly as described. The space felt fresh, organized, and welcoming from the moment we arrived.Overall, a great experience, and we would definitely stay here again. Highly recommend!"
United States
Shuo P.
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
Alpine 5, cozy Vermont retreat
Property grounds

Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"Very nice and relaxing location"
United States
Jennifer C.
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
Zen 10, relax and retreat in the heart of Vermont
1 bedroom, desk, iron/ironing board, travel crib

Oceans 8 minutes to Manchester Vermont

Oceans 8 minutes to Manchester Vermont
Manchester
8.0 out of 10, Very Good, (1 review)
The price is AED 289
AED 543 total
includes taxes & fees
25 Jun - 26 Jun
Oceans 8 minutes to Manchester Vermont
1 bedroom, desk, iron/ironing board, travel crib

3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
23 Jun - 24 Jun
3, cozy pet friendly Vermont retreat - two doubles
Exterior

Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
Room 2, double room - sleeps 4
1 bedroom, desk, iron/ironing board, travel crib

11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
11, Peaceful retreat in Vermont
Exterior

6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
6 Bam Boo Cozy escape in the heart of Vermont
Property grounds

Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
22 Jun - 23 Jun
Room 4 - Prickly Pear double room
1 bedroom, desk, iron/ironing board, travel crib

Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
24 Jun - 25 Jun
Cloud 9 family double sleeps 4
Exterior

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast
2.0 star property
Poultney
The price is AED 492
AED 536 total
includes taxes & fees
22 Jun - 23 Jun
Bentley House Bed and Breakfast
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

South Shire

South Shire

10/10 Excellent
"South Shire is a quaint Victorian Inn on Elm Street within walking distance to the center of Bennington, VT. The Inn has a family feel and elegance. We traveled as a couple. It was easy to get to sites and enjoy fine restaurants. The Inn is in keeping with the feel of strength of the Bennington community, as a place for artists, musicians, and people's expression generally to thrive. We enjoyed our stay and would recommend South Shire."
Peter 2-night trip
Posted 3 days ago
South Shire

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 onsite dining. 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.