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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Old Bennington bed & breakfast

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
$229 nightly
The price is $250
Dec 16 - Dec 17
Total with taxes and fees
The Four Chimneys Inn
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

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, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
$174 nightly
The price is $194
Dec 16 - Dec 17
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Porch
The Wilmington Inn

The Wilmington Inn

The Wilmington Inn
3.5 star property
Wilmington
10.0 out of 10, Exceptional, (196)
"Relaxing stay with great hiking nearby"
United States
Charlotte
$182 nightly
The price is $200
Dec 16 - Dec 17
Total with taxes and fees
The Wilmington Inn
TV
The Nutmeg

The Nutmeg

The Nutmeg
3.5 star property
Wilmington
9.4 out of 10, Exceptional, (414)
"This was a beautiful quaint property with delightful and attentive staff. The French toast breakfast was amazing! "
United States
John
$175 nightly
The price is $193
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Nutmeg
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
$187 nightly
The price is $206
Dec 17 - Dec 18
Total with taxes and fees
The Inn at Ormsby Hill
Garden
Big Bears Lodge

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
$167 nightly
The price is $183
Dec 16 - Dec 17
Total with taxes and fees
Big Bears Lodge
Front of property
Hill Farm Inn

Hill Farm Inn

Hill Farm Inn
4.0 star property
Arlington
9.6 out of 10, Exceptional, (173)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
$395 nightly
The price is $431
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hill Farm Inn
Property grounds
Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont
Manchester
10.0 out of 10, Exceptional, (1)
"Very nice and relaxing location"
United States
Jennifer C.
$117 nightly
The price is $130
Dec 16 - Dec 17
Total with taxes and fees
Zen 10, relax and retreat in the heart of Vermont
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (87)
"We had a lovely time staying here. "
United States
Jeff
$175 nightly
The price is $193
Dec 16 - Dec 17
Total with taxes and fees
Deerfield Valley Inn
TV
Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Manchester
$117 nightly
The price is $130
Dec 16 - Dec 17
Total with taxes and fees
Alpine 5, cozy Vermont retreat
Property grounds
Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
$117 nightly
The price is $130
Dec 16 - Dec 17
Total with taxes and fees
Room 7 - family room sleeps 4
1 bedroom, desk, iron/ironing board, travel crib
Oceans 8 minutes to Manchester Vermont

Oceans 8 minutes to Manchester Vermont

Oceans 8 minutes to Manchester Vermont
Manchester
$117 nightly
The price is $130
Dec 17 - Dec 18
Total with taxes and fees
Oceans 8 minutes to Manchester Vermont
1 bedroom, desk, iron/ironing board, travel crib
Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
$117 nightly
The price is $130
Dec 16 - Dec 17
Total with taxes and fees
Room 4 - Prickly Pear double room
Property grounds
Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4

Cloud 9 family double sleeps 4
Manchester
$117 nightly
The price is $130
Dec 17 - Dec 18
Total with taxes and fees
Cloud 9 family double sleeps 4
Exterior
6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont

6 Bam Boo Cozy escape in the heart of Vermont
Manchester
$117 nightly
The price is $130
Dec 17 - Dec 18
Total with taxes and fees
6 Bam Boo Cozy escape in the heart of Vermont
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 Old Bennington Hotel Reviews

Valley Craft Ales

Valley Craft Ales

10/10 Excellent
"Very easy check in process. They let us know due to it being a pub, it would be loud, but it was very quiet and easy to sleep! The pub area was lovely and had a huge chimney fire for everyone to enjoy and keep warm. The room was clean and well kept! Great experience! "
Karen 1-night trip
Posted 3 days ago
Valley Craft Ales

Find out more about Old Bennington

Old Bennington B&B information

Number of reviews
1,455
Accommodation
34 B&B
Lowest Price
$130
Highest Price
$431

Frequently asked questions

What is the nightly rate for a B&B in Old Bennington?
Prices for B&Bs in Old Bennington often vary, but you can find a great deal from $130 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Old Bennington B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Old Bennington B&B and a hotel?
Every Old Bennington B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Old Bennington B&Bs.

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