20 Best B&B in Bennington, VT - Bed and Breakfast from SAR 172

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.

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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

SAR 655 total

includes taxes & fees

16 Nov - 17 Nov

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

2. The Four Chimneys Inn

Bennington

Robert

SAR 917 total

includes taxes & fees

19 Nov - 20 Nov

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

3. Bromley View Inn

Bondville

BARBARA

SAR 316 total

includes taxes & fees

22 Nov - 23 Nov

A large, snow-covered house with multiple windows and a well-lit porch.

4. The Inn at Manchester

Manchester Village Historic District

Zhihao

SAR 662 total

includes taxes & fees

15 Nov - 16 Nov

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

SAR 897 total

includes taxes & fees

26 Nov - 27 Nov

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

6. Hill Farm Inn

Arlington

Jennifer

SAR 1,904 total

includes taxes & fees

16 Nov - 17 Nov

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

7. Alpine 5, cozy Vermont retreat

Manchester

Jean frandel

SAR 542 total

includes taxes & fees

23 Nov - 24 Nov

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

SAR 945 total

includes taxes & fees

22 Nov - 23 Nov

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

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

Manchester

Ivy B.

SAR 547 total

includes taxes & fees

18 Nov - 19 Nov

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

10. Room 7 - family room sleeps 4

Manchester

Kuan-Chung

SAR 547 total

includes taxes & fees

18 Nov - 19 Nov

11. Room 2, double room - sleeps 4

Manchester

Bowen S.

SAR 542 total

includes taxes & fees

30 Nov - 1 Dec

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

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

Manchester

Jennifer C.

SAR 547 total

includes taxes & fees

18 Nov - 19 Nov

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

13. Room 4 - Prickly Pear double room

Manchester

Kristin J.

SAR 544 total

includes taxes & fees

18 Nov - 19 Nov

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

Cheryl C.

SAR 556 total

includes taxes & fees

30 Nov - 1 Dec

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

Manchester

Bill W.

SAR 544 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Manchester

SAR 547 total

includes taxes & fees

18 Nov - 19 Nov

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

SAR 547 total

includes taxes & fees

18 Nov - 19 Nov

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

Manchester

SAR 547 total

includes taxes & fees

18 Nov - 19 Nov

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

19. Doveberry Inn

West Dover

Veronica

SAR 507 total

includes taxes & fees

19 Nov - 20 Nov

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

Ted

SAR 293 total

includes taxes & fees

25 Nov - 26 Nov

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Bennington and related destinations

Stroll through the charming downtown, 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

The Four Chimneys Inn

Bennington

10/10 Excellent

Randall

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

Hill Farm Inn

Arlington

10/10 Excellent

Michael

The Inn at Ormsby Hill

Manchester Center

10/10 Excellent

The Inn at Ormsby Hill is a magnificent B&B in historic Manchester Vermont. We were in Vermont for a ski week vacation. We ended our trip staying at this Inn and skiing at Stratton Ski Area. When we arrived, the Innkeeper Maryanne greeted us then suggested we move our room to one more centrally located. Our room was beautiful with a 4 post king bed, gas fireplace and plush bathrobes. The daily breakfast was superb! The dining area was full of antiques, many from the Pullman Corporation. Edward...

Anonymous traveler

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

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

North Shire Lodge

Manchester Center

10/10 Excellent

James

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.

The Trail in Adams - Berkshires’ Art Hotel

Adams

10/10 Excellent

Esther

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

Blue Gentian Lodge at Magic Mountain

Londonderry

10/10 Excellent

Anonymous traveler

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

Echo Lake Inn

Plymouth

10/10 Excellent

Deb

Doveberry Inn

West Dover

10/10 Excellent

This was a unique experience for me. It was like having a nice room in a log cabin. It was very quiet and peaceful right off the winding country road sitting in front of a forest with a beautiful outlook from the dining area. There was good self serve beverage options available when I arrived in the late evening and breakfast the next morning had enough quality items for a gluten free person like myself. No bread or baked goods for me but nice yogurt, fresh fruit and coffee. The owner Nick...

Hilda

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.

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. North Shire Lodge

6. Hill Farm Inn

7. Alpine 5, cozy Vermont retreat

8. The Inn at Ormsby Hill

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

10. Room 7 - family room sleeps 4

11. Room 2, double room - sleeps 4

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

13. Room 4 - Prickly Pear double room

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

15. Oceans 8 minutes to Manchester Vermont

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

17. Cloud 9 family double sleeps 4

18. 11, Peaceful retreat in Vermont

19. Doveberry Inn

20. Deerfield Valley Inn

Bennington and related destinations

Top reviews in Bennington

The Four Chimneys Inn

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Bennington?

Are you thinking about B&Bs over traditional hotel rooms?

What are the top B&Bs in Bennington?

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

What is there to do in Bennington?

How can I get to and around Bennington?