20 Best B&B in Bennington, VT - Bed and Breakfast from AED 287

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

Jeffrey

AED 685 total

includes taxes & fees

13 Nov - 14 Nov

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

2. The Four Chimneys Inn

Bennington

Robert

AED 897 total

includes taxes & fees

23 Nov - 24 Nov

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

3. Bromley View Inn

Bondville

BARBARA

AED 330 total

includes taxes & fees

29 Nov - 30 Nov

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

Zhihao

AED 648 total

includes taxes & fees

5 Nov - 6 Nov

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

5. Hill Farm Inn

Arlington

Jennifer

AED 1,863 total

includes taxes & fees

15 Nov - 16 Nov

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

6. The Inn at Ormsby Hill

Manchester Center

Victoria

AED 1,046 total

includes taxes & fees

10 Nov - 11 Nov

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.

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

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

8. Room 7 - family room sleeps 4

Manchester

Kuan-Chung

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

9. Room 2, double room - sleeps 4

Manchester

Bowen S.

AED 531 total

includes taxes & fees

16 Nov - 17 Nov

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.

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

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

11. Room 4 - Prickly Pear double room

Manchester

Kristin J.

AED 540 total

includes taxes & fees

9 Nov - 10 Nov

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.

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

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.

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

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.

AED 540 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Manchester

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

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

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

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

AED 531 total

includes taxes & fees

9 Nov - 10 Nov

A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

18. Doveberry Inn

West Dover

Veronica

AED 502 total

includes taxes & fees

11 Nov - 12 Nov

A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

19. Deerfield Valley Inn

West Dover

Ted

AED 287 total

includes taxes & fees

18 Nov - 19 Nov

A two-story house with a porch, a fountain, and a flag.

20. Bentley House Bed and Breakfast

Poultney

Juliet

AED 561 total

includes taxes & fees

5 Nov - 6 Nov

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Top Bennington Hotel Reviews

Hampton Inn Bennington

10/10 Excellent

"Everyone was great. Breakfast was delicious. They all go the extra mile. Thank you! See you in December"

Mountain Sanctuary Dome Rustic Solitude 5BR

8/10 Good

"We had an excellent stay at Nate’s place! Our group loved the architecture and the beautiful scenery. Kitchen tools could have been better, but we managed fine cooking for a group of 8. Plenty of sleeping space for a big group. Would recommend for a weekend away in VT!"

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."

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

10/10 Excellent

"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."

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.

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Our top choices for Bennington bed & breakfast

1. South Shire

2. The Four Chimneys Inn

3. Bromley View Inn

4. The Inn at Manchester

5. Hill Farm Inn

6. The Inn at Ormsby Hill

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

8. Room 7 - family room sleeps 4

9. Room 2, double 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. Doveberry Inn

19. Deerfield Valley Inn

20. Bentley House Bed and Breakfast

Top Bennington Hotel Reviews

Hampton Inn Bennington

Cozy Loft steps from VT Downtown

Hotel Vervana, Trademark Collection by Wyndham

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Mountain Sanctuary Dome Rustic Solitude 5BR

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

Starlight Inn

The Four Chimneys Inn

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Frequently asked questions

Explore a world of travel with Expedia

Search B&B in Bennington

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bennington bed & breakfast

1. South Shire

2. The Four Chimneys Inn

3. Bromley View Inn

4. The Inn at Manchester

5. Hill Farm Inn

6. The Inn at Ormsby Hill

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

8. Room 7 - family room sleeps 4

9. Room 2, double 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. Doveberry Inn

19. Deerfield Valley Inn

20. Bentley House Bed and Breakfast

Top Bennington Hotel Reviews

Hampton Inn Bennington

Frequently asked questions

Explore a world of travel with Expedia