Old Bennington Hotels

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Nov 30 - Dec 1
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Dec 1 - Dec 2
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Dec 5 - Dec 7
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Top 10 trending Old Bennington hotels

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, (1012)
"Staff was very nice!"
United States
David
The price is P6,279
P7,014 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
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, (442)
"It is the perfect place to stay!"
United States
Darrell
The price is P8,918
P11,271 total
includes taxes & fees
Dec 4 - Dec 5
The Porches Inn at Mass MoCA
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, (1004)
"Great location near historic downtown area, nice rooms. Overall, a very pleasant stay."
United States
Richard
The price is P6,130
P6,681 total
includes taxes & fees
Dec 9 - Dec 10
Hotel Vervana, Trademark Collection by Wyndham
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (762)
"It's very good for stay over"
United States
Frances
The price is P4,045
P4,519 total
includes taxes & fees
Dec 1 - Dec 2
The Villager Motel
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 P8,384
P9,365 total
includes taxes & fees
Dec 14 - Dec 15
Fairfield Inn & Suites by Marriott Williamstown
Front of property - evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (545)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is P11,556
P12,908 total
includes taxes & fees
Dec 1 - Dec 2
The Williams Inn
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (586)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is P5,804
P6,483 total
includes taxes & fees
Dec 1 - Dec 2
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 P5,218
P5,829 total
includes taxes & fees
Dec 1 - Dec 2
Williamstown Motel
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, (941)
"Great stay"
United States
TONY
The price is P6,202
P6,760 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Bennington
Front of property
Hill Farm Inn

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (172)
"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 P12,084
P26,364 total
includes taxes & fees
Dec 1 - Dec 2
Hill Farm Inn
Property grounds
Knotty Pine

Knotty Pine

2.5 star property
Bennington
9.0 out of 10, Wonderful, (26)
"The rooms were clean and well maintained. The staff was friendly. It is just a motel. "
United States
Martha
The price is P6,449
P7,030 total
includes taxes & fees
Dec 1 - Dec 2
Knotty Pine
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 P5,276
P5,893 total
includes taxes & fees
Dec 1 - Dec 2
Howard Johnson by Wyndham Williamstown
Reception
South Shire

South Shire

4.0 star property
Bennington
9.2 out of 10, Wonderful, (117)
"Beautiful place to stay "
United States
Jennifer
The price is P9,029
P10,186 total
includes taxes & fees
Dec 2 - Dec 3
South Shire
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
The price is P9,493
P12,054 total
includes taxes & fees
Dec 1 - Dec 2
Deerfield Valley Inn
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (990)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
The price is P4,485
P5,010 total
includes taxes & fees
Dec 1 - Dec 2
Willows Motel Williamstown
Living area
Chalet 239

Chalet 239

2.0 star property
West Dover
9.4 out of 10, Exceptional, (88)
"Great place for a quick trip to VT!"
United States
Rory
The price is P6,860
P7,546 total
includes taxes & fees
Dec 1 - Dec 2
Chalet 239
Exterior
Hampton Inn Bennington

Hampton Inn Bennington

2.5 star property
Bennington
8.6 out of 10, Excellent, (1006)
"Great place to rest and recharge. "
United States
Randy
The price is P8,125
P8,856 total
includes taxes & fees
Dec 7 - Dec 8
Hampton Inn Bennington
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 P11,667
P12,834 total
includes taxes & fees
Dec 1 - Dec 2
The Inn at Ormsby Hill
Interior detail
The White House Inn

The White House Inn

3.5 star property
Wilmington
9.2 out of 10, Wonderful, (255)
"The room was beautiful and the historic charm was wonderful "
United States
Karin
The price is P9,973
P10,970 total
includes taxes & fees
Dec 1 - Dec 2
The White House 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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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

Bennington Museum

4.4/5 (25 reviews)
You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.
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
Bennington Battle Monument which includes a monument and heritage elements

Top Old Bennington Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Wonderful Experience "
Chris 1-night trip
Posted 7 days ago
Hotel Downstreet, an Ascend Collection Hotel

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 P8,384 per night from Dec 14 to Dec 15
P8,384
P9,365 total
Dec 14 - Dec 15
includes taxes & fees
8.8/10 Excellent! (393 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.
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.
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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