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
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept
In one month
25 Sept - 27 Sept
In two months
23 Oct - 25 Oct

Our top choices for Bennington bed & breakfast

Library

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 HK$1,508
HK$1,729 total
includes taxes & fees
28 Aug - 29 Aug
South Shire
Lounge

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (469 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is HK$599
HK$659 total
includes taxes & fees
26 Aug - 27 Aug
Bromley View Inn
Room

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 HK$2,226
HK$2,426 total
includes taxes & fees
31 Aug - 1 Sept
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, (372 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is HK$1,093
HK$1,383 total
includes taxes & fees
8 Sept - 9 Sept
The Inn at Manchester
Exterior

5. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (163 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is HK$1,487
HK$1,636 total
includes taxes & fees
26 Aug - 27 Aug
North Shire Lodge
Front of property – evening/night

6. 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 HK$2,108
HK$2,319 total
includes taxes & fees
26 Aug - 27 Aug
The Inn at Ormsby Hill
Exterior

7. 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 HK$666
HK$1,212 total
includes taxes & fees
1 Sept - 2 Sept
Room 1, peaceful retreat in Manchester - King bed
Outdoor pool

8. 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 HK$2,343
HK$4,317 total
includes taxes & fees
26 Aug - 27 Aug
Hill Farm Inn
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 HK$699
HK$1,248 total
includes taxes & fees
2 Sept - 3 Sept
Room 7 - family room sleeps 4
Property grounds

10. 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 HK$666
HK$1,212 total
includes taxes & fees
31 Aug - 1 Sept
Zen 10, relax and retreat in the heart of Vermont
Room

11. 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 HK$741
HK$1,293 total
includes taxes & fees
26 Aug - 27 Aug
Oceans 8 minutes to Manchester Vermont
Room

12. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
The price is HK$691
HK$1,239 total
includes taxes & fees
8 Sept - 9 Sept
3, cozy pet friendly Vermont retreat - two doubles
Exterior

13. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is HK$617
HK$1,158 total
includes taxes & fees
31 Aug - 1 Sept
Room 2, double room - sleeps 4
Dining

14. 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 HK$666
HK$1,212 total
includes taxes & fees
31 Aug - 1 Sept
Alpine 5, cozy Vermont retreat
Room

15. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is HK$790
HK$1,348 total
includes taxes & fees
1 Sept - 2 Sept
Cloud 9 family double sleeps 4
Room

16. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is HK$666
HK$1,212 total
includes taxes & fees
1 Sept - 2 Sept
11, Peaceful retreat in Vermont
Property grounds

17. Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
The price is HK$782
HK$1,339 total
includes taxes & fees
26 Aug - 27 Aug
Room 4 - Prickly Pear double room
Exterior

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

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is HK$765
HK$1,321 total
includes taxes & fees
31 Aug - 1 Sept
6 Bam Boo Cozy escape in the heart of Vermont
Front of property

19. 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 HK$1,234
HK$1,358 total
includes taxes & fees
31 Aug - 1 Sept
Colonel Williams Inn
Outdoor wedding area

20. The Nutmeg

The Nutmeg
3.5 star property
Wilmington
9.4 out of 10, Exceptional, (440 reviews)
"Location and Friendly staff"
United States
David
The price is HK$1,411
HK$1,552 total
includes taxes & fees
27 Aug - 28 Aug
The Nutmeg
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

South Shire

South Shire

10/10 Excellent
"Super charming Victorian home. Perfect spot to disconnect and enjoy a restful stay"
Maria Belinda 1-night trip
Posted 1 day ago
South Shire

Find out more about Bennington

Bennington B&B information

Number of reviews
2,140
Accommodation
26 B&B
Lowest Price
HK$659
Highest Price
HK$4,317

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.

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