Book Hotels in Old Bennington, VT

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Top Old Bennington hotels

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
$725 nightly
The price is $812 total per night from Jul 12 to Jul 13
$812 total
Jul 12 - Jul 13
Total with taxes and fees
This apartment features a hot tub and a sauna. Laundry facilities and barbecue grills are also provided.
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on May 25, 2026

Opens in a new windowAmazing 34 foot high shipping container home in Whitingham on Sadawga Lake
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$281 nightly
The price is $314 total per night from Jul 27 to Jul 28
$314 total
Jul 27 - Jul 28
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 ...
"Great service and helpful friendly staff. Best spot to stay in town."

Reviewed on Jul 1, 2026

Opens in a new windowThe Williams Inn
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
$231 nightly
The price is $252 total per night from Jul 21 to Jul 22
$252 total
Jul 21 - Jul 22
Total with taxes and fees
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 ...
"Lovely place very comfortable"

Reviewed on Jul 3, 2026

Opens in a new windowThe Four Chimneys 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
$257 nightly
The price is $287 total per night from Aug 4 to Aug 5
$287 total
Aug 4 - Aug 5
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 ...
"So charming, so lovely. It exceeded our expectations and very much hope to return!"

Reviewed on Jul 2, 2026

Opens in a new windowThe Porches Inn at Mass MoCA
Brittany Motel

Brittany Motel

2 out of 5
1056 Main Street/Historic Route 7A Manchester Center VT
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $95 total per night from Jul 8 to Jul 9
$95 total
Jul 8 - Jul 9
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a snack bar/deli, and a library are also on offer.
"Staff was helpful, room was truly beautiful and beyond what most motels would offer. Though small-ish, the bathroom was impeccable. Lounge/kitchen was stocked with snacks and had microwave, fridge, utensils, tea/coffee/oatmeal for breakfast and was really handy. Saved time. Will recommend to ..."

Reviewed on Jul 4, 2026

Opens in a new windowBrittany Motel
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$170 nightly
The price is $190 total per night from Jul 12 to Jul 13
$190 total
Jul 12 - Jul 13
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 ...
"This hotel was very clean and nice. The staff was very friendly and helpful. Would definitely stay here again!"

Reviewed on Jul 5, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

3 out of 5
430 Main St Williamstown MA
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $245 total per night from Jul 12 to Jul 13
$245 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot ...
"Disappointed in the fact that the seating for breakfast was limited because of what appeared to be an issue the ceiling in the dining room. Hotel was full and seating in designated area was very limited and no alternative for seating other than carry back to you room."

Reviewed on Jun 26, 2026

Opens in a new windowFairfield Inn & Suites by Marriott Williamstown
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundable
$164 nightly
The price is $181 total per night from Aug 4 to Aug 5
$181 total
Aug 4 - Aug 5
Total with taxes and fees
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the gym and perks like free WiFi and a free area shuttle. ...
"ac had to be turned back on every few hours. fridge broke three times and maintenance needed to bring new ones. pool and hot tub was closed even tho i specifically bought this booking because expedia said it was available. fire pit was nice and they had a great fourth of july celebration"

Reviewed on Jul 5, 2026

Opens in a new windowGrand Summit Resort, A Vail Resorts Property
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $124 total per night from Jul 12 to Jul 13
$124 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool ...
"Disappointing."

Reviewed on Jul 4, 2026

Opens in a new windowHotel Vervana, Trademark Collection by Wyndham
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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 $95. 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 1,020 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.

Recent Old Bennington hotel reviews by fellow wanderers

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"This hotel was very clean and nice. The staff was very friendly and helpful. Would definitely stay here again!"
A verified traveler stayed at Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel

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