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

Bed and Breakfast 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
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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, (135 reviews)
"Probably the best and most romantic place in Bennington"
United States
Jorge
The price is NZ$431
includes taxes & fees
26 Oct - 27 Oct
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, (485 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is NZ$185
includes taxes & fees
1 Oct - 2 Oct
Bromley View Inn
A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

3. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (164 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is NZ$404
includes taxes & fees
1 Oct - 2 Oct
North Shire Lodge
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, (384 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
The price is NZ$434
includes taxes & fees
31 Oct - 1 Nov
The Inn at Manchester
A grassy area with trees, a building, and red chairs.

5. Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
10.0 out of 10, Exceptional, (1 review)
"Awesome place to stay - loved it!"
United States
Kristin J.
The price is NZ$272
includes taxes & fees
1 Oct - 2 Oct
Room 4 - Prickly Pear double room
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, (180 reviews)
"Our favorite place to stay!!"
United States
Jennifer
The price is NZ$978
includes taxes & fees
25 Oct - 26 Oct
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 NZ$697
includes taxes & fees
19 Oct - 20 Oct
The Inn at Ormsby Hill
A grassy area with a large tree, red chairs, and a building in the background.

8. Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont
Manchester
9.6 out of 10, Exceptional, (4 reviews)
"Very nice and relaxing location"
United States
Jennifer C.
The price is NZ$295
includes taxes & fees
20 Oct - 21 Oct
Zen 10, relax and retreat in the heart of Vermont
A cozy hotel room with a bed, a desk, a chair, a small table, and a window with curtains.

9. Oceans 8 minutes to Manchester Vermont

Oceans 8 minutes to Manchester Vermont
Manchester
8.0 out of 10, Very good, (2 reviews)
"Our dogs and I had a great stay"
United States
Bill W.
The price is NZ$297
includes taxes & fees
20 Oct - 21 Oct
Oceans 8 minutes to Manchester Vermont
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

10. Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Cute little motel. Place was clean and the host was very helpful with any questions I had. The fire area was nice to go relax at the end of the day. Highly recommended a visit if your in the at area."
United States
Ivy B.
The price is NZ$283
includes taxes & fees
19 Oct - 20 Oct
Room 1, peaceful retreat in Manchester - King bed
A grassy outdoor area with red Adirondack chairs and a fire pit.

11. 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 NZ$272
includes taxes & fees
1 Oct - 2 Oct
Room 7 - family room sleeps 4
A residential area with houses and a well-lit driveway at dusk.

12. 6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is NZ$322
includes taxes & fees
20 Oct - 21 Oct
6 Bam Boo Cozy escape in the heart of Vermont
A bedroom with a bed, a heart-shaped pillow, and a framed artwork of a cloud on the wall.

13. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is NZ$279
includes taxes & fees
1 Oct - 2 Oct
Cloud 9 family double sleeps 4
A small room with a table and two chairs, a window with curtains, and a lamp on the table.

14. 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 NZ$275
includes taxes & fees
20 Oct - 21 Oct
Alpine 5, cozy Vermont retreat
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

15. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is NZ$267
includes taxes & fees
20 Oct - 21 Oct
Room 2, double room - sleeps 4
A cozy room with a bed, a sofa, a wooden table, and a coffee machine.

16. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
8.0 out of 10, Very good, (1 review)
"The room was clean."
United States
George R.
The price is NZ$261
includes taxes & fees
20 Oct - 21 Oct
3, cozy pet friendly Vermont retreat - two doubles
A bedroom with a large painting of a cow, a tufted headboard, and a bed with patterned bedding and decorative pillows.

17. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is NZ$301
includes taxes & fees
1 Oct - 2 Oct
11, Peaceful retreat in Vermont
A bedroom with a bed, dresser, TV, and a chair.

18. Doveberry Inn

Doveberry Inn
3.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
The price is NZ$232
includes taxes & fees
27 Oct - 28 Oct
Doveberry Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

19. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (359 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 NZ$277
includes taxes & fees
6 Oct - 7 Oct
Colonel Williams Inn
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

20. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (133 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is NZ$289
includes taxes & fees
21 Oct - 22 Oct
Deerfield Valley 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

Knotty Pine

Knotty Pine

10/10 Excellent
"We had a nice stay at the Knotty Pine Motel. The room was clean, spacious, and comfortable, and check-in was quick and easy. Overall, everything was well kept and made for a pleasant stay. The only downside for me was that the bed was a bit harder than I prefer, but that’s a personal preference. Overall, a good place to stay, definitely would stay there again."
Scott 2-night trip
Posted 18 hours ago
Knotty Pine

Find out more about Bennington

Bennington B&B information

Number of reviews
1,360
Accommodation
26 B&B
Lowest Price
NZ$185
Highest Price
NZ$978

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 Prospect Mountain Nordic Ski Center and Prospect Mountain Cross-Country Ski Center. You should put Woodford State Park and Green Mountain National Forest 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