Photo by Justin Hunter

Find a Bed and Breakfast in Old Bennington from CA $73

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Check prices for these dates

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

Our top choices for Old Bennington bed & breakfast

A large, two-story house with a covered porch and multiple chimneys.

1. 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 CA $316
CA $345 total
includes taxes & fees
Nov 23 - Nov 24
The Four Chimneys Inn
A room with wooden paneling, a piano, a chair, and a door leading to another room.

2. 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 CA $212
CA $246 total
includes taxes & fees
Nov 17 - Nov 18
South Shire
A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

3. 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 CA $172
CA $190 total
includes taxes & fees
Nov 12 - Nov 13
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.

4. 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 CA $73
CA $119 total
includes taxes & fees
Nov 19 - Nov 20
Deerfield Valley Inn
A stone fire pit surrounded by a grassy area with a tree and outdoor seating.

5. The Nutmeg

The Nutmeg
3.5 star property
Wilmington
9.4 out of 10, Exceptional, (444 reviews)
"The property was beautiful! Our check in was easy. The room was clean and bedding was very comfortable. Breakfast was also delicious."
United States
Susan
The price is CA $254
CA $280 total
includes taxes & fees
Nov 17 - Nov 18
The Nutmeg
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
The price is CA $307
CA $338 total
includes taxes & fees
Nov 26 - Nov 27
North Shire Lodge
A wooden sign with an arrow pointing to the right, labeled "CHICKENS".

7. The Wilmington Inn

The Wilmington Inn
3.5 star property
Wilmington
10.0 out of 10, Exceptional, (213 reviews)
"Wonderful property. Great locations. Breakfast was the best of any on our trip!"
United States
Jay
The price is CA $253
CA $286 total
includes taxes & fees
Nov 16 - Nov 17
The Wilmington Inn
A small room with a table and two chairs, a window with curtains, and a lamp on the table.

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 CA $119
CA $205 total
includes taxes & fees
Nov 23 - Nov 24
Alpine 5, cozy Vermont retreat
A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

9. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (222 reviews)
"Welcoming host with great customer service"
United States
Alfred
The price is CA $244
CA $268 total
includes taxes & fees
Dec 4 - Dec 5
Big Bears Lodge
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

10. 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 CA $325
CA $357 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Ormsby Hill
A swimming pool with a view of a barn and mountains in the background.

11. 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 CA $366
CA $716 total
includes taxes & fees
Nov 24 - Nov 25
Hill Farm Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

12. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is CA $245
CA $274 total
includes taxes & fees
Nov 15 - Nov 16
The Trail in Adams - Berkshires’ Art Hotel
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.
The price is CA $119
CA $205 total
includes taxes & fees
Nov 30 - Dec 1
Room 2, double room - sleeps 4
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

14. 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 CA $121
CA $207 total
includes taxes & fees
Nov 18 - Nov 19
Room 1, peaceful retreat in Manchester - King bed
A cozy room with a bed, a sofa, a wooden table, and a coffee machine.

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.
The price is CA $121
CA $207 total
includes taxes & fees
Nov 18 - Nov 19
3, cozy pet friendly Vermont retreat - two doubles
A grassy outdoor area with red Adirondack chairs and a fire pit.

16. 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 CA $121
CA $207 total
includes taxes & fees
Nov 18 - Nov 19
Room 7 - family room sleeps 4
A grassy area with a large tree, red chairs, and a building in the background.

17. 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 CA $121
CA $207 total
includes taxes & fees
Nov 18 - Nov 19
Zen 10, relax and retreat in the heart of Vermont
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 CA $121
CA $207 total
includes taxes & fees
Nov 18 - Nov 19
11, Peaceful retreat in Vermont
A grassy area with trees, a building, and red chairs.

19. 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 CA $124
CA $210 total
includes taxes & fees
Nov 18 - Nov 19
Room 4 - Prickly Pear double room
A cozy hotel room with a bed, a desk, a chair, a small table, and a window with curtains.

20. 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 CA $124
CA $210 total
includes taxes & fees
Nov 18 - Nov 19
Oceans 8 minutes to Manchester Vermont
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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Learn more about Old Bennington

Explore attractions like Old First Congregational Church and Bennington Museum as you discover things to see and do in Old Bennington.

See all hotels in Old Bennington
A tall, narrow obelisk with a pointed top, surrounded by trees and a clear blue sky.
Photo by Justin Hunter
Open Photo by Justin Hunter

Top reviews in Old Bennington

A room with wooden paneling, a piano, a chair, and a door leading to another room.
South Shire

South Shire

South Shire
Bennington

10/10 Excellent

A+ service, room we stayed in was perfect size with king bed. had an issue with heater first night but Inn Keeper was great to deal with and provided alternative heat source on first evening plus they have working fireplace (bonus++). We stayed 3 nights and just enjoyed ourselves during our visit. would definitely stay here again.
Canada
TROY
Reviewed January 5, 2026
South Shire

Frequently Asked Questions

Searching for B&Bs in Old Bennington?

If you want to find a place to stay with fewer rooms than a hotel and a more personalized environment, a B&B might be just the right fit for your vacation to Old Bennington. When you want to venture out to explore Old Bennington, consider browsing the exhibits at Bennington Museum.

How do you know if a B&B is the best choice for your stay?

Every B&B has its own unique feel. Whether it’s a garden for guests to admire or a beautiful breakfast room, the small details are what make bed and breakfasts a fun place to get away.

What are the best bed and breakfasts in Old Bennington?

Here are some B&Bs in the surrounding area: The Four Chimneys Inn: 11 rooms. 0.2 mi (0.3 km) from the heart of Old Bennington. Enjoy the free full breakfast and unique décor. South Shire: 9 rooms. 0.8 mi (1.4 km) from the downtown core. Enjoy the massage services and bar/lounge. Big Bears Lodge: 24 rooms. Located 17.5 mi (28.2 km) from the core of Old Bennington. Enjoy the free cooked breakfast and outdoor pool.

When is the best time to book my B&B in Old Bennington?

When you're planning your escape to Old 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 Old Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.

What is there to do in Old Bennington?

When you want to explore some things to do in town, Old First Congregational Church and Bennington Museum are some notable sights to visit. You might also consider a trip to sites like Bennington Center for the Arts or Robert Frost Stone House Museum if you have time to see more of the area.

How can I get to and around Old Bennington?

Planning your excursions in and around Old Bennington is easier with these transportation options. Fly into Albany Intl. Airport (ALB), which is located 31.7 mi (51 km) away from the heart of the city. If you'd like to explore around the area, consider renting a car to take in more sights.

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