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

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Bennington bed & breakfast

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1. South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (131 reviews)
"Super charming Victorian home. Perfect spot to disconnect and enjoy a restful stay"
United States
Maria Belinda
The price is ￥33,176
￥37,906 total
includes taxes & fees
Sep 1 - Sep 2
South Shire
Lounge

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (472 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is ￥12,240
￥13,463 total
includes taxes & fees
Aug 30 - Aug 31
Bromley View Inn
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10

3. 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 ￥45,474
￥49,567 total
includes taxes & fees
Aug 31 - Sep 1
The Four Chimneys 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, (373 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is ￥26,655
￥33,721 total
includes taxes & fees
Aug 30 - Aug 31
The Inn at Manchester
Exterior

5. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (164 reviews)
"Wonderful find in Vermont. The staff provides what you need while maintaining a room for your privacy. Everything is in the vincinity with each access."
United States
Libin K
The price is ￥30,377
￥33,416 total
includes taxes & fees
Aug 30 - Aug 31
North Shire Lodge
Exterior

6. 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 ￥13,784
￥24,944 total
includes taxes & fees
Sep 1 - Sep 2
Room 1, peaceful retreat in Manchester - King bed
Outdoor pool

7. 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 ￥47,867
￥88,197 total
includes taxes & fees
Aug 30 - Aug 31
Hill Farm Inn
Front of property - evening/night

8. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (172 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is ￥68,679
￥75,547 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Ormsby Hill
Property grounds

9. 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 ￥14,288
￥25,498 total
includes taxes & fees
Aug 30 - Aug 31
Room 7 - family room sleeps 4
Dining

10. 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 ￥13,616
￥24,758 total
includes taxes & fees
Aug 31 - Sep 1
Alpine 5, cozy Vermont retreat
Property grounds

11. Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
10.0 out of 10, Exceptional, (1 review)
"Awesome place to stay - loved it!"
United States
Kristin J.
The price is ￥17,314
￥29,007 total
includes taxes & fees
Sep 9 - Sep 10
Room 4 - Prickly Pear double room
Room

12. 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 ￥16,809
￥28,271 total
includes taxes & fees
Aug 31 - Sep 1
Oceans 8 minutes to Manchester Vermont
Property grounds

13. 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 ￥17,314
￥29,007 total
includes taxes & fees
Sep 9 - Sep 10
Zen 10, relax and retreat in the heart of Vermont
Exterior

14. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is ￥12,607
￥23,650 total
includes taxes & fees
Aug 31 - Sep 1
Room 2, double room - sleeps 4
Room

15. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is ￥12,607
￥23,650 total
includes taxes & fees
Aug 31 - Sep 1
11, Peaceful retreat in Vermont
Exterior

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

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is ￥13,111
￥24,204 total
includes taxes & fees
Aug 30 - Aug 31
6 Bam Boo Cozy escape in the heart of Vermont
Room

17. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
The price is ￥13,952
￥25,128 total
includes taxes & fees
Sep 8 - Sep 9
3, cozy pet friendly Vermont retreat - two doubles
Room

18. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is ￥14,288
￥25,498 total
includes taxes & fees
Aug 30 - Aug 31
Cloud 9 family double sleeps 4
Standard Double Room

19. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
The price is ￥23,238
￥25,561 total
includes taxes & fees
Sep 6 - Sep 7
Doveberry Inn
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 ￥25,214
￥27,735 total
includes taxes & fees
Aug 31 - Sep 1
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.
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Top Bennington Hotel Reviews

Knotty Pine

Knotty Pine

8/10 Good
"Very well maintained establishment. Room was clearly as advertised. Easy check-in and check out. Pool was very clean. Plenty of parking for the vehicles safely. Only concern was the empty supplied shampoo. Luckily I brought my own. Towels, linens and kitchenette was clean and ready to use. Would definitely book here again when I the area."
Hawk 1-night trip
Posted 2 hours ago
Knotty Pine

Find out more about Bennington

Bennington B&B information

Number of reviews
2,943
Accommodation
26 B&B
Lowest Price
￥13,463
Highest Price
￥88,197

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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