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Find hotels in Old Bennington, VT from ￥15,441

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Compare 994 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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

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
The Four Chimneys Inn
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1003)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ￥16,636
￥18,583 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
Garden
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 star property
Bennington
8.2 out of 10, Very Good, (1001)
"Great location near historic downtown area, nice rooms. Overall, a very pleasant stay."
United States
Richard
The price is ￥15,712
￥17,127 total
includes taxes & fees
Dec 24 - Dec 25
Hotel Vervana, Trademark Collection by Wyndham
In-room safe, blackout drapes, iron/ironing board
Best Western Bennington

Best Western Bennington

2.5 star property
Bennington
7.6 out of 10, Good, (942)
"Great stay"
United States
TONY
The price is ￥16,479
￥17,963 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Bennington
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
The price is ￥10,718
￥11,972 total
includes taxes & fees
Dec 10 - Dec 11
The Villager Motel
Suite, 2 Bedrooms | Frette Italian sheets, premium bedding, down comforters, minibar
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (445)
"It is the perfect place to stay!"
United States
Darrell
The price is ￥22,379
￥28,478 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Porches Inn at Mass MoCA
Front of property - evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is ￥29,390
￥32,828 total
includes taxes & fees
Dec 24 - Dec 25
The Williams Inn
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
Williamstown
8.8 out of 10, Excellent, (394)
"our stay was great."
United States
nathaniel
The price is ￥24,387
￥27,241 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Fairfield Inn & Suites by Marriott Williamstown
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (588)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is ￥15,378
￥17,177 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Maple Terrace Motel
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (314)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
The price is ￥13,824
￥15,441 total
includes taxes & fees
Dec 10 - Dec 11
Williamstown Motel
Front of property
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
The price is ￥26,500
￥63,939 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hill Farm Inn
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
Deerfield Valley Inn
Family Room | Living area | Smart TV
Chalet 239

Chalet 239

2.0 star property
West Dover
9.4 out of 10, Exceptional, (89)
"Great place for a quick trip to VT!"
United States
Rory
The price is ￥20,191
￥22,210 total
includes taxes & fees
Dec 10 - Dec 11
Chalet 239
Exterior
Hampton Inn Bennington

Hampton Inn Bennington

2.5 star property
Bennington
8.6 out of 10, Excellent, (1001)
"Great place to rest and recharge. "
United States
Randy
The price is ￥21,063
￥22,958 total
includes taxes & fees
Dec 23 - Dec 24
Hampton Inn Bennington
Property grounds
Knotty Pine

Knotty Pine

2.5 star property
Bennington
9.2 out of 10, Wonderful, (28)
"The rooms were clean and well maintained. The staff was friendly. It is just a motel. "
United States
Martha
The price is ￥17,086
￥18,624 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Knotty Pine
Reception
South Shire

South Shire

4.0 star property
Bennington
9.2 out of 10, Wonderful, (118)
"Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!"
United States
Roseann
The price is ￥24,881
￥28,818 total
includes taxes & fees
Dec 18 - Dec 19
South Shire
Interior detail
The White House Inn

The White House Inn

3.5 star property
Wilmington
9.2 out of 10, Wonderful, (260)
"The room was beautiful and the historic charm was wonderful "
United States
Karin
The price is ￥25,723
￥28,295 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The White House Inn
Pool
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

2.0 star property
Williamstown
6.6 out of 10, (899)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is ￥13,978
￥15,612 total
includes taxes & fees
Dec 20 - Dec 21
Howard Johnson by Wyndham Williamstown
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (992)
"Warm welcome. Great location. Best fresh fruit breakfast ever."
United States
Melissa
The price is ￥11,883
￥13,273 total
includes taxes & fees
Dec 24 - Dec 25
Willows Motel Williamstown
Front of property
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
The price is ￥30,911
￥34,002 total
includes taxes & fees
Dec 10 - Dec 11
The Inn at Ormsby Hill
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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Stay near popular Old Bennington attractions

Bennington Battle Monument

4.5/5 (124 reviews)
Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.
See properties

Old First Congregational Church

4.8/5 (4 reviews)
Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.
See properties

Learn more about Old Bennington

Explore attractions like Old First Congregational Church and Bennington Museum as you discover things to see and do in Old Bennington.

See all hotels in Old Bennington
The monument commemorates the Battle of Bennington during the American Revolutionary War. You can purchase a ticket for 5$ and ride the elevator 2/3 of the way up and see the beautiful sights from all around. A beautiful place to visit.
Photo by Justin Hunter
Open Photo by Justin Hunter

Top Old Bennington Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. "
Stacey 1-night trip
Posted 2 days ago
The Williams Inn

More cheap stays in Old Bennington

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

430 Main St Williamstown MA
The price is ￥24,387 per night from Jan 8 to Jan 9
￥24,387
￥27,241 total
Jan 8 - Jan 9, 2026
includes taxes & fees
8.8/10 Excellent! (394 reviews)

Frequently asked questions

Where is the best place for a stay in Old Bennington?
Based on our traveler data, The Four Chimneys Inn is one of the top choices for your stay. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Hotel Downstreet, an Ascend Collection Hotel and The Williams Inn. See all available top hotels, or vacation rentals in Old Bennington.
What are some of the best vacation home rentals in Old Bennington?
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.: Visitors like this Old Bennington vacation home rental. It is located in the mountains and has a fireplace, a patio, and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub. See all vacation rentals in Old Bennington.
If I need to cancel my hotel reservation in Old Bennington, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Old Bennington.
Where can I learn more about changing or cancelling my trip to Old Bennington?
To access more information about picking new dates or cancelling your trip to Old Bennington, click here.
How is it to stay in Old Bennington?
Visitors are sure to enjoy all that Old Bennington has to offer. A top sight in the area is Mount Snow. There are 990 hotels and other accommodations in the surrounding area. Find out more about Old Bennington.
What should I see while I'm in Old Bennington?
Landmarks like Old First Congregational Church and Bennington Battle Monument might be worth a visit. Additionally, you'll find Mount Snow in the area. Check out what more to see and do in Expedia's Old Bennington guide.
What's the weather like in Old Bennington?
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 Old Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.

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