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
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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
9.0 out of 10, Wonderful, (141 reviews)
"Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants."
United States
Jeffrey
The price is €158
includes taxes & fees
15 Nov - 16 Nov
South Shire
A large, two-story house with a covered porch and multiple chimneys.

2. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.6 out of 10, Exceptional, (291 reviews)
"We enjoyed our stay."
United States
Robert
The price is €221
includes taxes & fees
23 Nov - 24 Nov
The Four Chimneys Inn
A deck with white railings overlooking a forested area and a mountain in the distance.

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (504 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
The price is €73
includes taxes & fees
22 Nov - 23 Nov
Bromley View Inn
A large, snow-covered house with multiple windows and a well-lit porch.

4. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (404 reviews)
"Great place. Great host!"
United States
Zhihao
The price is €160
includes taxes & fees
16 Nov - 17 Nov
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, (165 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is €217
includes taxes & fees
26 Nov - 27 Nov
North Shire Lodge
A large, white two-story house with a stone wall and yellow flowers in the foreground.

6. 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 €228
includes taxes & fees
13 Dec - 14 Dec
The Inn at Ormsby Hill
A two-story house with a porch and outdoor seating area.

7. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.8 out of 10, Exceptional, (182 reviews)
"Our favorite place to stay!!"
United States
Jennifer
The price is €459
includes taxes & fees
16 Nov - 17 Nov
Hill Farm Inn
A bedroom with a bed, a bedside table with a lamp and a plant, a window with curtains, and a wall-mounted picture.

8. Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Manchester
7.6 out of 10, Good, (4 reviews)
"Good Service and good place to stay in Vermont!"
United States
Jean frandel
The price is €134
includes taxes & fees
18 Nov - 19 Nov
Alpine 5, cozy Vermont retreat
A grassy outdoor area with red Adirondack chairs and a fire pit.

9. 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
Room 7 - family room sleeps 4
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 €135
includes taxes & fees
18 Nov - 19 Nov
Room 1, peaceful retreat in Manchester - King bed
A grassy area with a large tree, red chairs, and a building in the background.

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

Zen 10, relax and retreat in the heart of Vermont
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"Very nice and relaxing location"
United States
Jennifer C.
Zen 10, relax and retreat in the heart of Vermont
A grassy area with trees, a building, and red chairs.

12. 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.
Room 4 - Prickly Pear double room
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

13. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
9.0 out of 10, Wonderful, (2 reviews)
"Great spot"
United States
Bowen S.
Room 2, double room - sleeps 4
A grassy area with a large tree, a building, and red chairs.

14. 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.
Oceans 8 minutes to Manchester Vermont
A two-story house with a covered patio, outdoor seating, and a well-maintained garden.

15. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
8.0 out of 10, Very good, (2 reviews)
"Great place! Loved the shared full kitchen! Loved all the seating outdoors to enjoy the mountains!!! Was centrally located to enjoy surrounding areas. Host was very responsive to questions."
United States
Cheryl C.
3, cozy pet friendly Vermont retreat - two doubles
A grassy area with a large tree, red chairs, and a building in the background.

16. 6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
6 Bam Boo Cozy escape in the heart of Vermont
A grassy outdoor area with red Adirondack chairs and a fire pit.

17. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
Cloud 9 family double sleeps 4
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

18. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
11, Peaceful retreat in Vermont
A two-story house with a red roof and grey siding, a front porch, and a stack of firewood.

19. 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 €121
includes taxes & fees
16 Nov - 17 Nov
Doveberry Inn
A two-story house with a porch, a fountain, and a flag.

20. Bentley House Bed and Breakfast

Bentley House Bed and Breakfast
2.0 star property
Poultney
10.0 out of 10, Exceptional, (45 reviews)
"Great Unique home, very kind couple that owns the place!"
United States
Juliet
The price is €146
includes taxes & fees
16 Nov - 17 Nov
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.
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Top Bennington Hotel Reviews

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

10/10 Excellent
"We loved our stay! Chris as extremely communicative and accommodating. 10/10 highly recommend."
Angela R. 14-night trip
Posted 9 hours ago
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Find out more about Bennington

Bennington B&B information

Number of reviews
1,098
Accommodation
26 B&B
Lowest Price
€73
Highest Price
€459

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.