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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Bennington bed & breakfast

Living area

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 £137
includes taxes & fees
21 Nov - 22 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 £182
includes taxes & fees
2 Dec - 3 Dec
The Four Chimneys Inn
A cozy room with a fireplace, green sofas, a pool table, and a lamp.

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 £67
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, (402 reviews)
"Great place. Great host!"
United States
Zhihao
The price is £131
includes taxes & fees
9 Nov - 10 Nov
The Inn at Manchester
A swimming pool with a view of a barn and mountains in the background.

5. 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 £369
includes taxes & fees
8 Dec - 9 Dec
Hill Farm Inn
A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

6. 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
North Shire Lodge
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 £185
includes taxes & fees
8 Dec - 9 Dec
The Inn at Ormsby Hill
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

8. 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 £110
includes taxes & fees
16 Nov - 17 Nov
Room 1, peaceful retreat in Manchester - King bed
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
The price is £109
includes taxes & fees
16 Nov - 17 Nov
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 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.
The price is £109
includes taxes & fees
16 Nov - 17 Nov
Room 2, double room - sleeps 4
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.
The price is £109
includes taxes & fees
16 Nov - 17 Nov
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.
The price is £109
includes taxes & fees
16 Nov - 17 Nov
Room 4 - Prickly Pear double room
A cozy room with a bed, a sofa, a wooden table, and a coffee machine.

13. 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.
The price is £109
includes taxes & fees
16 Nov - 17 Nov
3, cozy pet friendly Vermont retreat - two doubles
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 £110
includes taxes & fees
16 Nov - 17 Nov
Alpine 5, cozy Vermont retreat
A cozy hotel room with a bed, a desk, a chair, a small table, and a window with curtains.

15. 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 £108
includes taxes & fees
16 Nov - 17 Nov
Oceans 8 minutes to Manchester Vermont
A residential area with houses and a well-lit driveway at dusk.

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

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is £109
includes taxes & fees
16 Nov - 17 Nov
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.

17. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is £110
includes taxes & fees
16 Nov - 17 Nov
Cloud 9 family double sleeps 4
A bedroom with a large painting of a cow, a tufted headboard, and a bed with patterned bedding and decorative pillows.

18. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is £110
includes taxes & fees
16 Nov - 17 Nov
11, Peaceful retreat in Vermont
A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

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 £102
includes taxes & fees
16 Nov - 17 Nov
Doveberry 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, (140 reviews)
"A very quaint, cozy inn set in West Dover, Vermont. We had a small room but it was clean and comfortable. We didn't choose to order breakfast while we were there but it smelled wonderful! Oz, the host, was professional, pleasant, and helpful."
United States
Ted
The price is £58
includes taxes & fees
22 Nov - 23 Nov
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.
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Bennington and related destinations

Stroll through the charming city centre, where the Bennington Museum showcases local art and the famous 'Bennington Flag.' Hike up to the Bennington Battle Monument for panoramic views, then explore the covered bridges and Robert Frost's grave in nearby North Bennington.

See all hotels in Bennington
A mountainous landscape with autumn foliage, a prominent church spire, and a winding road.

Top reviews in Bennington

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
Four Columns Inn

Four Columns Inn

Four Columns Inn
Newfane

8/10 Good

We only had an opportunity to stay one night stay but overall had a very pleasant experience. The room was really nice apart from the wierd location of the television . The bar was "like a real bar " and the lady serving was great ( as was the live entertainment ). Our dining experience has room for improvement although the staff were really nice . Breakfast was "OK" . Good coffee . The owner was extremely friendly and the location and grounds are beautiful . Check in was a little fluffy - I...
United Kingdom
Philip
Reviewed August 3, 2026
Four Columns Inn

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.