Old Bennington Hotels from S$106

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Old Bennington hotels

The Four Chimneys Inn
4.0 star property
9.4 out of 10, Exceptional, (280)
"Nice and cozy"
The Four Chimneys Inn
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1006)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
The price is S$188
includes taxes & fees
11 Nov - 12 Nov
Hotel Downstreet, an Ascend Collection Hotel
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (304)
"The rooms are dated but very clean and neat. This family run motel is convenient to everything in Williamstown and the university. The check-in was easy and staff were knowledgeable and kind."
The price is S$112
includes taxes & fees
2 Nov - 3 Nov
Williamstown Motel
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (520)
"Nice place to stay for a wedding "
The price is S$307
includes taxes & fees
2 Nov - 3 Nov
The Williams Inn
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (426)
"Great hotel, lovely pool and hot tub. We got upgraded to a suite!"
The price is S$262
includes taxes & fees
11 Nov - 12 Nov
The Porches Inn at Mass MoCA
Howard Johnson by Wyndham Williamstown
2.0 star property
6.6 out of 10, (887)
"Great affordable place to stay while in the northern Berkshires."
The price is S$159
includes taxes & fees
14 Oct - 15 Oct
Howard Johnson by Wyndham Williamstown
The Villager Motel
2.0 star property
8.8 out of 10, Excellent, (748)
"Perfect location for our passing through vacay."
The price is S$114
includes taxes & fees
2 Nov - 3 Nov
The Villager Motel
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (385)
"our stay was great."
The price is S$207
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Williamstown
Hotel Vervana, Trademark Collection by Wyndham
2.5 star property
8.2 out of 10, Very good, (1007)
"Friendly staff easy check in accessible to different places"
The price is S$153
includes taxes & fees
2 Nov - 3 Nov
Hotel Vervana, Trademark Collection by Wyndham
Maple Terrace Motel
2.5 star property
9.6 out of 10, Exceptional, (581)
"Excellent place. Bountiful view. "
The price is S$143
includes taxes & fees
2 Nov - 3 Nov
Maple Terrace Motel
Best Western Bennington
2.5 star property
7.6 out of 10, Good, (929)
"Great stay"
The price is S$150
includes taxes & fees
2 Nov - 3 Nov
Best Western Bennington
Willows Motel Williamstown
2.0 star property
9.0 out of 10, Wonderful, (961)
"Good breakfast; comfortable beds; smiling service; great tv; very accomodating"
The price is S$129
includes taxes & fees
20 Oct - 21 Oct
Willows Motel Williamstown
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (137)
"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "
The price is S$252
includes taxes & fees
22 Oct - 23 Oct
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
3.0 star property
8.8 out of 10, Excellent, (19)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
The price is S$252
includes taxes & fees
14 Oct - 15 Oct
The Revival House
Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (872)
"Very nice staff, nice breakfast"
The price is S$114
includes taxes & fees
2 Nov - 3 Nov
Cozy Corner Motel
Deerfield Valley Inn
3.0 star property
9.6 out of 10, Exceptional, (69)
"We had a lovely time staying here. "
Deerfield Valley Inn
Knotty Pine
2.5 star property
9.2 out of 10, Wonderful, (5)
"Very nice and nostalgic. Close to all amenities, friendly front staff. I would definitely stay again if in the area. 1 small critique... bed was a little firm for my liking. Again i would highly recommend and stay again."
The price is S$218
includes taxes & fees
23 Oct - 24 Oct
Knotty Pine
Brook Bound Inn
2.0 star property
9.4 out of 10, Exceptional, (10)
"Great property. Amazing views!"
Brook Bound Inn
Arlington Inn
3.0 star property
8.8 out of 10, Excellent, (180)
"Excellent stay! Very friendly staff."
The price is S$271
includes taxes & fees
21 Oct - 22 Oct
Arlington Inn
Chalet 239
2.0 star property
9.4 out of 10, Exceptional, (80)
"I was pleasantly surprised in how well well-maintained this property was. Beautiful decor, impeccably clean, and extremely comfortable bed and linens. We were in a king room with a little deck off the back. It was just lovely to sit outside and have a glass of wine. Check in and check out was a breeze and this adorable hotel is in a perfect location. I would definitely stay here again and recommend to others. "
The price is S$167
includes taxes & fees
2 Nov - 3 Nov
Chalet 239
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Old Bennington attractions

Learn more about Old Bennington

Venture to sights like Old First Congregational Church and Bennington Museum as you discover Old Bennington.

Bennington Battle Monument which includes landscape views

Top Old Bennington Hotel Reviews

More cheap stays in Old Bennington

Frequently asked questions

Where is the best place for a stay in Old Bennington?
Based on our traveller data, The Four Chimneys Inn is one of the top choices for your stay. This B&B offers free breakfast and free parking. Other good choices for your visit to the area are The Williams Inn and Hotel Downstreet, an Ascend Collection Hotel. 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! The majority of room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it 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 staying in Old Bennington?
Visitors will definitely enjoy all that Old Bennington has to offer. There are 974 hotels and other accommodation options in the surrounding area. Find out more about Old Bennington.
What are the top places to visit in Old Bennington?
Landmarks like Old First Congregational Church and Bennington Battle Monument might be worth a visit. Additionally, you might want to add Bennington Museum to your itinerary. Take a look at what more there is 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Old Bennington are January, March, February and December, with each month seeing an average of 21 cm of snowfall.

Explore a world of travel with Expedia