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

Bed and Breakfast in Bennington

  • 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
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sept - 13 Sept
In two months
9 Oct - 11 Oct

Our top choices for Bennington bed & breakfast

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10

1. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (290 reviews)
"Peaceful and whimsical stay in a historic inn. The breakfast was delicious (served with the best local maple syrup) and location was a 5 minute drive to the downtown area."
United States
Jeane
The price is NZ$473
includes taxes & fees
18 Aug - 19 Aug
The Four Chimneys Inn
Library

2. South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (129 reviews)
"Staff was great."
United States
Jan
The price is NZ$402
includes taxes & fees
18 Aug - 19 Aug
South Shire
Lounge

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (463 reviews)
"Very helpful and clean right on the"
United States
Leonard a moultom
The price is NZ$143
includes taxes & fees
17 Aug - 18 Aug
Bromley View Inn
Property grounds

4. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (368 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is NZ$299
includes taxes & fees
8 Sept - 9 Sept
The Inn at Manchester
Exterior

5. Victorian mansions Coach Room with Breakfast

Victorian mansions Coach Room with Breakfast
Bennington
Victorian mansions Coach Room with Breakfast
Exterior

6. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (162 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is NZ$354
includes taxes & fees
17 Aug - 18 Aug
North Shire Lodge
Front of property – evening/night

7. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (171 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is NZ$502
includes taxes & fees
18 Aug - 19 Aug
The Inn at Ormsby Hill
Exterior

8. 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 NZ$272
includes taxes & fees
1 Sept - 2 Sept
Room 1, peaceful retreat in Manchester - King bed
Outdoor pool, pool loungers

9. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (179 reviews)
"Our favorite place to stay!!"
United States
Jennifer
The price is NZ$690
includes taxes & fees
14 Sept - 15 Sept
Hill Farm Inn
Property grounds

10. 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 NZ$268
includes taxes & fees
17 Aug - 18 Aug
Room 7 - family room sleeps 4
Property grounds

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

Zen 10, relax and retreat in the heart of Vermont
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"Very nice and relaxing location"
United States
Jennifer C.
The price is NZ$304
includes taxes & fees
1 Sept - 2 Sept
Zen 10, relax and retreat in the heart of Vermont
Dining

12. Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Manchester
6.8 out of 10, (3 reviews)
"We had a wonderful stay! The room was very clean and spacious, which made it extremely comfortable and relaxing. Everything was well maintained and exactly as described. The space felt fresh, organized, and welcoming from the moment we arrived.Overall, a great experience, and we would definitely stay here again. Highly recommend!"
United States
Shuo P.
The price is NZ$268
includes taxes & fees
17 Aug - 18 Aug
Alpine 5, cozy Vermont retreat
1 bedroom, desk, iron/ironing board, travel cot

13. Oceans 8 minutes to Manchester Vermont

Oceans 8 minutes to Manchester Vermont
Manchester
8.0 out of 10, Very good, (1 review)
The price is NZ$296
includes taxes & fees
17 Aug - 18 Aug
Oceans 8 minutes to Manchester Vermont
1 bedroom, desk, iron/ironing board, travel cot

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

3, cozy pet friendly Vermont retreat - two doubles
Manchester
The price is NZ$259
includes taxes & fees
24 Aug - 25 Aug
3, cozy pet friendly Vermont retreat - two doubles
Exterior

15. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is NZ$260
includes taxes & fees
18 Aug - 19 Aug
Room 2, double room - sleeps 4
1 bedroom, desk, iron/ironing board, travel cot

16. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is NZ$272
includes taxes & fees
1 Sept - 2 Sept
11, Peaceful retreat in Vermont
1 bedroom, desk, iron/ironing board, travel cot

17. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is NZ$296
includes taxes & fees
17 Aug - 18 Aug
Cloud 9 family double sleeps 4
Property grounds

18. Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
The price is NZ$296
includes taxes & fees
17 Aug - 18 Aug
Room 4 - Prickly Pear double room
Exterior

19. 6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is NZ$333
includes taxes & fees
1 Sept - 2 Sept
6 Bam Boo Cozy escape in the heart of Vermont
Front of property

20. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is NZ$284
includes taxes & fees
23 Aug - 24 Aug
Colonel Williams Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Knotty Pine

Knotty Pine

8/10 Good
"Rooms are a good size, beds are comfortable."
Barbara 1-night trip
Posted 9 hours ago
Knotty Pine

Find out more about Bennington

Bennington B&B information

Number of reviews
1,534
Accommodation
26 B&B
Lowest Price
NZ$143
Highest Price
NZ$690

Frequently asked questions

Searching for B&Bs in Bennington?
If you're hoping for something a little different than your standard 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 interested in an apartment for your stay?
B&Bs all have a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook, the small details are what make bed and breakfasts a home away from home.
What are the top B&Bs in Bennington?
Here are some B&Bs to look at 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 decor.
What's the best time of year 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Bennington are January, March, February and December, with each month seeing an average of 21 cm of snowfall.
What is there to do in Bennington?
If you're looking for some things to do on you trip, travellers 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 should 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?
Planning your excursions in and around Bennington is easier with these transportation options. Fly into Albany, NY (ALB-Albany Intl.), which is located 31.7 mi (51 km) away. Otherwise, look 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