Book Hotels in Old Bennington, VT

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Top Old Bennington hotels

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road, Bennington, VT
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi ...
"This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was ..."

Reviewed on Sep 2, 2025

Opens in a new windowThe Four Chimneys Inn
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $250 total per night from Oct 29 to Oct 30
$250 total
Oct 29 - Oct 30
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference ...
"Very helpful and friendly front desk staff. The room was lovely!"

Reviewed on Sep 25, 2025

Opens in a new windowThe Williams Inn
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street, North Adams, MA
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $256 total per night from Sep 30 to Oct 1
$256 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the ...
"True to its historic character, the attention to detail was splendid!"

Reviewed on Sep 24, 2025

Opens in a new windowThe Porches Inn at Mass MoCA
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $162 total per night from Oct 28 to Oct 29
$162 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
a gem
"Totally perfect for mass mocha"

Reviewed on Sep 21, 2025

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Sep 30 to Oct 1
$127 total
Sep 30 - Oct 1
Total with taxes and fees
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are ...
"There was no staff on duty and the carpet in the room was not vacuumed and there was no ice machine"

Reviewed on Sep 23, 2025

Opens in a new windowMountaineer Inn
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way, West Dover, VT
Fully refundable
$153 nightly
The price is $168 total per night from Oct 30 to Oct 31
$168 total
Oct 30 - Oct 31
Total with taxes and fees
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free ...
"Great place to stay!"

Reviewed on Sep 25, 2025

Opens in a new windowMount Snow Grand Summit Resort
Valley Craft Ales

Valley Craft Ales

2 out of 5
18 N Main St, Wilmington, VT
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Oct 27 to Oct 28
$97 total
Oct 27 - Oct 28
Total with taxes and fees
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a communal living room are also ...
"Very clean and comfortable room with an excellent view of the stream and the trees outside. No TV in the room; perfect for anyone looking for a night away. The walls are thin so if you are sensitive to noise I would not recommend as I could clearly hear my neighbor snoring, however ear plugs are ..."

Reviewed on Sep 25, 2025

Opens in a new windowValley Craft Ales
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Oct 19 to Oct 20
$133 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. ...
"Great stay"

Reviewed on Sep 23, 2025

Opens in a new windowBest Western Bennington
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

2 out of 5
213 Main St, Williamstown, MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Sep 30 to Oct 1
$123 total
Sep 30 - Oct 1
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the ...
"Clean room!"

Reviewed on Sep 7, 2025

Opens in a new windowHoward Johnson by Wyndham Williamstown
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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.

Frequently asked questions

What are the top kid-friendly hotels in Old Bennington?
Take some of the hassles out of traveling with young ones by booking a family-friendly Old Bennington hotel. From entertaining amenities to more services, these properties feature perks that'll make your getaway plain sailing: You'll be well looked after at The Four Chimneys Inn. It comes with complimentary breakfast, a picnic area and a commitment to making families feel welcome. Also check out the deals at Paradise Inn. It offers a swimming pool, a tennis court and lots of opportunities for precious family time.
Where can I find cheap hotels in Old Bennington?
At Travelocity you'll find really nice hotels in Old Bennington at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Old Bennington rather than in Old Bennington. We may find you even better rates, too.
How do I find the best Old Bennington hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Old Bennington then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Old Bennington?
The cheapest hotel in Old Bennington is $97. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Old Bennington?
There are 973 hotels in Old Bennington on Travelocity.
What are the best hotels in Old Bennington?
Old Bennington has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Old Bennington for you!
When is the best time to visit Old Bennington?
If you want the joy of a fun-filled trip in peak season, visit Old Bennington during January, April and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as August, October and November.
When is the cheapest time to stay in Old Bennington?
Based on historic data is usually the cheapest month to visit Old Bennington. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Old Bennington?
There are multiple hotels in Old Bennington that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Old Bennington. We have plenty of kid-friendly hotels in Old Bennington to choose from on Travelocity!
Why book a hotel in Old Bennington through Travelocity?
Because we have the top hotels in Old Bennington! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Old Bennington on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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