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
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 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, (129 reviews)
"Staff was great."
United States
Jan
The price is AED 761
AED 869 total
includes taxes & fees
11 Aug - 12 Aug
South Shire
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, iron/ironing board, WiFi (free), individually decorated

2. 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 AED 939
AED 1,023 total
includes taxes & fees
18 Aug - 19 Aug
The Four Chimneys Inn
Lounge

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (456 reviews)
"staff actually treated you like family and not another customer & Clean room & relaxing backyard to watch the sunset & great breakfast"
United States
Josh
The price is AED 281
AED 309 total
includes taxes & fees
10 Aug - 11 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, (361 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is AED 612
AED 774 total
includes taxes & fees
10 Aug - 11 Aug
The Inn at Manchester
Exterior

5. 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 AED 693
AED 762 total
includes taxes & fees
17 Aug - 18 Aug
North Shire Lodge
Exterior

6. Victorian mansions Coach Room with Breakfast

Victorian mansions Coach Room with Breakfast
Bennington
The price is AED 777
AED 994 total
includes taxes & fees
9 Aug - 10 Aug
Victorian mansions Coach Room with Breakfast
Outdoor pool, sun loungers

7. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (177 reviews)
"This is our fourth time staying. We love the inn. Very cozy vibes, restaurant on site is delicious. Very close to Manchester, which has great shops and restaurants."
United States
Jennifer
The price is AED 988
AED 1,904 total
includes taxes & fees
9 Aug - 10 Aug
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, (169 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is AED 988
AED 1,087 total
includes taxes & fees
18 Aug - 19 Aug
The Inn at Ormsby Hill
Dining

9. 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 289
AED 543 total
includes taxes & fees
10 Aug - 11 Aug
Alpine 5, cozy Vermont retreat
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 AED 289
AED 543 total
includes taxes & fees
11 Aug - 12 Aug
Zen 10, relax and retreat in the heart of Vermont
Property grounds

11. 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 289
AED 543 total
includes taxes & fees
9 Aug - 10 Aug
Room 7 - family room sleeps 4
Exterior

12. Room 2, double room - sleeps 4

Room 2, double room - sleeps 4
Manchester
The price is AED 289
AED 543 total
includes taxes & fees
10 Aug - 11 Aug
Room 2, double room - sleeps 4
Exterior

13. 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 332
AED 589 total
includes taxes & fees
11 Aug - 12 Aug
6 Bam Boo Cozy escape in the heart of Vermont
1 bedroom, desk, iron/ironing board, travel crib

14. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is AED 359
AED 619 total
includes taxes & fees
1 Sep - 2 Sep
11, Peaceful retreat in Vermont
Exterior

15. 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 359
AED 619 total
includes taxes & fees
1 Sep - 2 Sep
Room 1, peaceful retreat in Manchester - King bed
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 366
AED 627 total
includes taxes & fees
17 Aug - 18 Aug
3, cozy pet friendly Vermont retreat - two doubles
1 bedroom, desk, iron/ironing board, travel crib

17. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is AED 390
AED 653 total
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 AED 390
AED 653 total
includes taxes & fees
17 Aug - 18 Aug
Room 4 - Prickly Pear double room
1 bedroom, desk, iron/ironing board, travel crib

19. 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 AED 301
AED 555 total
includes taxes & fees
9 Aug - 10 Aug
Oceans 8 minutes to Manchester 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 AED 579
AED 636 total
includes taxes & fees
9 Aug - 10 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.
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Top Bennington Hotel Reviews

Knotty Pine

Knotty Pine

10/10 Excellent
"It was honestly a lovely place to stay! They had a small green area to walk our dog with a trash can for easy pet poop disposal. The room was spacious and had a small desk and a small table."
Shannon 1-night trip
Posted 11 hours ago
Knotty Pine

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 Harmon Hill and Prospect Mountain Nordic 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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