20 Best B&B in Bennington, VT - Bed and Breakfast from ￥12,349

Q: 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 bar/lounge. The Four Chimneys Inn : 11 rooms. Enjoy the free full breakfast and unique décor.

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

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

In two weeks

In one month

In two months

Our top choices for Bennington bed & breakfast

A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

1. The Four Chimneys Inn

Bennington

Robert

￥33,928 total

includes taxes & fees

Nov 1 - Nov 2

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

2. South Shire

Bennington

Jorge

￥35,650 total

includes taxes & fees

Nov 7 - Nov 8

A cozy room with a fireplace, green sofas, a pool table, and a lamp.

3. Bromley View Inn

Bondville

BARBARA

￥13,505 total

includes taxes & fees

Nov 1 - Nov 2

A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

4. The Inn at Manchester

Manchester Village Historic District

Reagan

￥27,898 total

includes taxes & fees

Nov 9 - Nov 10

A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

5. North Shire Lodge

Manchester Center

Jesse

￥31,196 total

includes taxes & fees

Oct 18 - Oct 19

A swimming pool with a view of a barn and mountains in the background.

6. Hill Farm Inn

Arlington

Jennifer

￥80,198 total

includes taxes & fees

Nov 15 - Nov 16

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

Manchester Center

Victoria

￥44,588 total

includes taxes & fees

Nov 15 - Nov 16

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

Manchester

Ivy B.

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A grassy outdoor area with red Adirondack chairs and a fire pit.

9. Room 7 - family room sleeps 4

Manchester

Kuan-Chung

￥23,391 total

includes taxes & fees

Nov 9 - Nov 10

A grassy area with a large tree, red chairs, and a building in the background.

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

Manchester

Jennifer C.

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A grassy area with trees, a building, and red chairs.

11. Room 4 - Prickly Pear double room

Manchester

Kristin J.

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A cozy room with a bed, a sofa, a wooden table, and a coffee machine.

12. 3, cozy pet friendly Vermont retreat - two doubles

Manchester

Cheryl C.

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A small room with a table and two chairs, a window with curtains, and a lamp on the table.

13. Alpine 5, cozy Vermont retreat

Manchester

Shuo P.

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A cozy hotel room with a bed, a desk, a chair, a small table, and a window with curtains.

14. Oceans 8 minutes to Manchester Vermont

Manchester

Bill W.

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A residential area with houses and a well-lit driveway at dusk.

15. 6 Bam Boo Cozy escape in the heart of Vermont

Manchester

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

A bedroom with a bed, a heart-shaped pillow, and a framed artwork of a cloud on the wall.

16. Cloud 9 family double sleeps 4

Manchester

￥23,391 total

includes taxes & fees

Nov 2 - Nov 3

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

Manchester

18. Room 2, double room - sleeps 4

Manchester

￥23,391 total

includes taxes & fees

Oct 20 - Oct 21

A bedroom with a bed, dresser, TV, and a chair.

19. Doveberry Inn

West Dover

Veronica

￥20,893 total

includes taxes & fees

Oct 29 - Oct 30

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

West Dover

Patrick

￥12,349 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good

"Pet friendly…if you are in building 3 you are pretty far from breakfast and lobby"

Knotty Pine

8/10 Good

"I felt a little abandoned by the manager because she had very limite hours when she was available. The was pleasant and responsive when we did see her, but . . . Bathroom was clean and all, but design didn't allow space for a woman to lay out makeup and personal items. Very limited. Beds were very comfortable. Glad to have frig and microwave."

Starlight Inn

8/10 Good

"Very nice old school Vermont motor inn. Dated decor, but all clean and well maintained. Except the shower. The shower was clean, but even with only a few people in the motel getting consistent hot/cold water was difficult. Literally our only complaint. Very good location to downtown, too. Only about 4 1/2 miles from Bennington College if you are visiting."

Find out more about Bennington

Bennington B&B information

Number of reviews	1,666
Accommodation	26 B&B
Lowest Price	￥12,349
Highest Price	￥80,198

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 bar/lounge. 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 Prospect Mountain Nordic Ski Center and Prospect Mountain Cross-Country Ski Center. You might 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?

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.

Explore a world of travel with Expedia

More ways to book

Book B&B in Bennington on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bennington bed & breakfast

1. The Four Chimneys Inn

2. South Shire

3. Bromley View Inn

4. The Inn at Manchester

5. North Shire Lodge

6. Hill Farm Inn

7. The Inn at Ormsby Hill

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

9. Room 7 - family room sleeps 4

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

11. Room 4 - Prickly Pear double room

12. 3, cozy pet friendly Vermont retreat - two doubles

13. Alpine 5, cozy Vermont retreat

14. Oceans 8 minutes to Manchester Vermont

15. 6 Bam Boo Cozy escape in the heart of Vermont

16. Cloud 9 family double sleeps 4

17. 11, Peaceful retreat in Vermont

18. Room 2, double room - sleeps 4

19. Doveberry Inn

20. Deerfield Valley Inn

Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hampton Inn Bennington

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Knotty Pine

South Shire

Starlight Inn

Cozy Loft steps from VT Downtown

The Four Chimneys Inn

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Find out more about Bennington

Bennington B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find Bennington Bed And Breakfast

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bennington bed & breakfast

1. The Four Chimneys Inn

2. South Shire

3. Bromley View Inn

4. The Inn at Manchester

5. North Shire Lodge

6. Hill Farm Inn

7. The Inn at Ormsby Hill

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

9. Room 7 - family room sleeps 4

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

11. Room 4 - Prickly Pear double room

12. 3, cozy pet friendly Vermont retreat - two doubles

13. Alpine 5, cozy Vermont retreat

14. Oceans 8 minutes to Manchester Vermont

15. 6 Bam Boo Cozy escape in the heart of Vermont

16. Cloud 9 family double sleeps 4

17. 11, Peaceful retreat in Vermont

18. Room 2, double room - sleeps 4

19. Doveberry Inn

20. Deerfield Valley Inn

Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Bennington B&B information

Frequently asked questions

Explore a world of travel with Expedia