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
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

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 HK$1,626
HK$1,858 total
includes taxes & fees
16 Aug - 17 Aug
South Shire
Premium bedding, iron/ironing board, free WiFi, 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 HK$2,005
HK$2,185 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, (458 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 HK$600
HK$660 total
includes taxes & fees
16 Aug - 17 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, (364 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is HK$1,094
HK$1,384 total
includes taxes & fees
7 Sept - 8 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, (162 reviews)
"Fantastic stay, wonderful staff."
United States
Jesse
The price is HK$1,489
HK$1,638 total
includes taxes & fees
12 Aug - 13 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, (171 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is HK$2,110
HK$2,321 total
includes taxes & fees
24 Aug - 25 Aug
The Inn at Ormsby Hill
Outdoor pool, pool loungers

7. Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (178 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 HK$2,111
HK$4,066 total
includes taxes & fees
12 Aug - 13 Aug
Hill Farm Inn
Exterior

8. Victorian mansions Coach Room with Breakfast

Victorian mansions Coach Room with Breakfast
Bennington
The price is HK$1,844
HK$2,394 total
includes taxes & fees
24 Aug - 25 Aug
Victorian mansions Coach Room with Breakfast
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$700
HK$1,250 total
includes taxes & fees
17 Aug - 18 Aug
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$873
HK$1,449 total
includes taxes & fees
31 Aug - 1 Sept
Zen 10, relax and retreat in the heart of Vermont
Exterior

11. 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$741
HK$1,295 total
includes taxes & fees
1 Sept - 2 Sept
Room 1, peaceful retreat in Manchester - King bed
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 HK$717
HK$1,268 total
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 HK$815
HK$1,376 total
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 HK$651
HK$1,195 total
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 HK$816
HK$1,376 total
includes taxes & fees
25 Aug - 26 Aug
Room 2, double room - sleeps 4
1 bedroom, desk, iron/ironing board, travel cot

16. Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
The price is HK$815
HK$1,376 total
includes taxes & fees
17 Aug - 18 Aug
Cloud 9 family double sleeps 4
Property grounds

17. Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
The price is HK$815
HK$1,376 total
includes taxes & fees
17 Aug - 18 Aug
Room 4 - Prickly Pear double room
1 bedroom, desk, iron/ironing board, travel cot

18. 11, Peaceful retreat in Vermont

11, Peaceful retreat in Vermont
Manchester
The price is HK$741
HK$1,295 total
includes taxes & fees
1 Sept - 2 Sept
11, Peaceful retreat in Vermont
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 HK$1,038
HK$1,657 total
includes taxes & fees
25 Aug - 26 Aug
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 HK$1,236
HK$1,359 total
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.
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Top Bennington Hotel Reviews

Lake life at Woodford Cottage

Lake life at Woodford Cottage

10/10 Excellent
"We were 4 nurses from Maine in Bennington volunteering at the annual RAM clinic. We put in long hours and were so grateful to have a clean, comfortable, safe place to lay our heads down at night. A dip in the pond after clinic was a refreshing treat! House was clean, well supplied and well stocked. Hosts were responsive and welcoming. 10/10 would recommend!"
Alison G. 2-night trip
Posted 8 hours ago
Lake life at Woodford Cottage

Find out more about Bennington

Bennington B&B information

Number of reviews
1,987
Accommodation
26 B&B
Lowest Price
HK$660
Highest Price
HK$4,066

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 Harmon Hill and Prospect Mountain Nordic 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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