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
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Bennington bed & breakfast

Library

1. South Shire

South Shire
4.0 star property
Bennington
9.0 out of 10, Wonderful, (134 reviews)
"Probably the best and most romantic place in Bennington"
United States
Jorge
The price is AED 803
AED 916 total
includes taxes & fees
24 Sep - 25 Sep
South Shire
Property grounds

2. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (381 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
The price is AED 777
AED 983 total
includes taxes & fees
21 Sep - 22 Sep
The Inn at Manchester
Exterior

3. North Shire Lodge

North Shire Lodge
3.0 star property
Manchester Center
9.4 out of 10, Exceptional, (164 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is AED 760
AED 836 total
includes taxes & fees
21 Sep - 22 Sep
North Shire Lodge
Exterior

4. 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 AED 312
AED 568 total
includes taxes & fees
21 Sep - 22 Sep
Room 1, peaceful retreat in Manchester - King bed
Outdoor pool, sun loungers

5. 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 AED 1,098
AED 2,024 total
includes taxes & fees
21 Sep - 22 Sep
Hill Farm Inn
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 AED 1,319
AED 1,450 total
includes taxes & fees
21 Sep - 22 Sep
The Inn at Ormsby Hill
Property grounds

7. 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 AED 312
AED 568 total
includes taxes & fees
21 Sep - 22 Sep
Room 7 - family room sleeps 4
Property grounds

8. 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 AED 312
AED 568 total
includes taxes & fees
21 Sep - 22 Sep
Room 4 - Prickly Pear double room
Property grounds

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

Zen 10, relax and retreat in the heart of Vermont
Manchester
9.6 out of 10, Exceptional, (4 reviews)
"Very nice and relaxing location"
United States
Jennifer C.
The price is AED 312
AED 568 total
includes taxes & fees
21 Sep - 22 Sep
Zen 10, relax and retreat in the heart of Vermont
1 bedroom, desk, iron/ironing board, travel crib

10. Oceans 8 minutes to Manchester Vermont

Oceans 8 minutes to Manchester Vermont
Manchester
8.0 out of 10, Very good, (2 reviews)
"Our dogs and I had a great stay"
United States
Bill W.
The price is AED 328
AED 585 total
includes taxes & fees
21 Sep - 22 Sep
Oceans 8 minutes to Manchester Vermont
Dining

11. 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 AED 312
AED 568 total
includes taxes & fees
21 Sep - 22 Sep
Alpine 5, cozy Vermont retreat
Exterior

12. 6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
The price is AED 328
AED 585 total
includes taxes & fees
21 Sep - 22 Sep
6 Bam Boo Cozy escape in the heart of Vermont
1 bedroom, desk, iron/ironing board, travel crib

13. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is AED 297
AED 551 total
includes taxes & fees
29 Sep - 30 Sep
11, Peaceful retreat in Vermont
1 bedroom, desk, iron/ironing board, travel crib

14. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is AED 370
AED 632 total
includes taxes & fees
22 Sep - 23 Sep
Cloud 9 family double sleeps 4
Exterior

15. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is AED 339
AED 598 total
includes taxes & fees
29 Sep - 30 Sep
Room 2, double room - sleeps 4
1 bedroom, desk, iron/ironing board, travel crib

16. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
The price is AED 409
AED 674 total
includes taxes & fees
24 Sep - 25 Sep
3, cozy pet friendly Vermont retreat - two doubles
Standard Double Room | WiFi (free)

17. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
The price is AED 510
AED 561 total
includes taxes & fees
19 Oct - 20 Oct
Doveberry Inn
Front of property

18. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (359 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 AED 555
AED 611 total
includes taxes & fees
21 Oct - 22 Oct
Colonel Williams Inn
Exterior

19. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (133 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is AED 352
AED 488 total
includes taxes & fees
21 Sep - 22 Sep
Deerfield Valley Inn
Terrace/patio

20. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (156 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is AED 608
AED 679 total
includes taxes & fees
21 Sep - 22 Sep
The Trail in Adams - Berkshires’ Art Hotel
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
"Romantic old Victorian with charming decor. Nice walkable distance to downtown."
Kimberly 1-night trip
Posted 5 days ago
South Shire

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 Woodford State Park 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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