20 Best B&B in Bennington, VT - Bed and Breakfast from ￥13,439

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.

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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

Bennington

Maria Belinda

￥37,837 total

includes taxes & fees

Sep 7 - Sep 8

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

2. Bromley View Inn

Bondville

William

￥13,439 total

includes taxes & fees

Sep 3 - Sep 4

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

3. The Four Chimneys Inn

Bennington

Jeane

￥66,019 total

includes taxes & fees

Sep 3 - Sep 4

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

Lori

￥28,200 total

includes taxes & fees

Sep 9 - Sep 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

Libin K

￥33,353 total

includes taxes & fees

Sep 7 - Sep 8

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

6. Hill Farm Inn

Arlington

Jennifer

￥87,376 total

includes taxes & fees

Sep 15 - Sep 16

A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

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

Manchester

Ivy B.

￥25,635 total

includes taxes & fees

Sep 7 - Sep 8

A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

8. The Inn at Ormsby Hill

Manchester Center

Victoria

￥74,167 total

includes taxes & fees

Sep 15 - Sep 16

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

9. Room 7 - family room sleeps 4

Manchester

Kuan-Chung

￥26,559 total

includes taxes & fees

Sep 7 - Sep 8

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

10. Room 4 - Prickly Pear double room

Manchester

Kristin J.

￥28,769 total

includes taxes & fees

Sep 29 - Sep 30

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

Manchester

Jennifer C.

￥28,769 total

includes taxes & fees

Sep 29 - Sep 30

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

12. Alpine 5, cozy Vermont retreat

Manchester

Shuo P.

￥26,375 total

includes taxes & fees

Sep 29 - Sep 30

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

13. Oceans 8 minutes to Manchester Vermont

Manchester

￥27,666 total

includes taxes & fees

Sep 7 - Sep 8

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

14. 3, cozy pet friendly Vermont retreat - two doubles

Manchester

￥23,975 total

includes taxes & fees

Sep 7 - Sep 8

15. Room 2, double room - sleeps 4

Manchester

￥23,975 total

includes taxes & fees

Sep 15 - Sep 16

A bedroom with a large painting of a cow, a tufted headboard, and a bed with patterned bedding and decorative pillows.

16. 11, Peaceful retreat in Vermont

Manchester

￥25,703 total

includes taxes & fees

Sep 7 - Sep 8

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

Manchester

￥29,029 total

includes taxes & fees

Sep 7 - Sep 8

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

18. 6 Bam Boo Cozy escape in the heart of Vermont

Manchester

￥32,268 total

includes taxes & fees

Sep 15 - Sep 16

A large white building with a stone wall and a lawn covered in fallen leaves.

19. Colonel Williams Inn

Brattleboro

Robert

￥27,284 total

includes taxes & fees

Sep 15 - Sep 16

A stone fire pit surrounded by a grassy area with a tree and outdoor seating.

20. The Nutmeg

Wilmington

Madison

￥31,639 total

includes taxes & fees

Sep 6 - Sep 7

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Top Bennington Hotel Reviews

Knotty Pine

8/10 Good

"Clean and convenient."

Bennington Motor Inn

8/10 Good

"It was handy to everywhere in Bennington (which, admittedly is a small town)and was a fine place to stay. Parking was a bit dicey, being on a steep side hill, and the main walkway out front ( a first floor balcony) was tilted a bit away from the building- a drink and I might have been over into the driveway. I would stay there again."

Lake life at Woodford Cottage

10/10 Excellent

"We were 4 nurses from Maine in Bennington volunteering at the annual RAM clinic. We put in long hours and were so grateful to have a clean, comfortable, safe place to lay our heads down at night. A dip in the pond after clinic was a refreshing treat! House was clean, well supplied and well stocked. Hosts were responsive and welcoming. 10/10 would recommend!"

Find out more about Bennington

Bennington B&B information

Number of reviews	2,217
Accommodation	26 B&B
Lowest Price	￥13,439
Highest Price	￥87,376

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 Bennington Museum and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display 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.

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Book B&B in Bennington on Expedia.com

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Check prices for these dates

Our top choices for Bennington bed & breakfast

1. South Shire

2. Bromley View Inn

3. The Four Chimneys Inn

4. The Inn at Manchester

5. North Shire Lodge

6. Hill Farm Inn

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

8. The Inn at Ormsby Hill

9. Room 7 - family room sleeps 4

10. Room 4 - Prickly Pear double room

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

12. Alpine 5, cozy Vermont retreat

13. Oceans 8 minutes to Manchester Vermont

14. 3, cozy pet friendly Vermont retreat - two doubles

15. Room 2, double room - sleeps 4

16. 11, Peaceful retreat in Vermont

17. Cloud 9 family double sleeps 4

18. 6 Bam Boo Cozy escape in the heart of Vermont

19. Colonel Williams Inn

20. The Nutmeg

Top Bennington Hotel Reviews

Knotty Pine

Perfect for a peaceful get away in clean fresh Vermont air!

Hampton Inn Bennington

Hotel Vervana, Trademark Collection by Wyndham

South Shire

Starlight Inn

Charming 2-bedroom apartment in superb Bennington with WiFi

Bennington Motor Inn

Lake life at Woodford Cottage

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. South Shire

2. Bromley View Inn

3. The Four Chimneys Inn

4. The Inn at Manchester

5. North Shire Lodge

6. Hill Farm Inn

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

8. The Inn at Ormsby Hill

9. Room 7 - family room sleeps 4

10. Room 4 - Prickly Pear double room

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

12. Alpine 5, cozy Vermont retreat

13. Oceans 8 minutes to Manchester Vermont

14. 3, cozy pet friendly Vermont retreat - two doubles

15. Room 2, double room - sleeps 4

16. 11, Peaceful retreat in Vermont

17. Cloud 9 family double sleeps 4

18. 6 Bam Boo Cozy escape in the heart of Vermont

19. Colonel Williams Inn

20. The Nutmeg

Top Bennington Hotel Reviews

Knotty Pine

Find out more about Bennington

Bennington B&B information

Frequently asked questions

Explore a world of travel with Expedia