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
$249 nightly
The price is $271 total per night from Nov 1 to Nov 2
$271 total
Nov 1 - Nov 2
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 ...
"Very nice, quiet place. Relaxing and cute."

Reviewed on Sep 7, 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
$189 nightly
The price is $211 total per night from Nov 5 to Nov 6
$211 total
Nov 5 - Nov 6
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 ...
"The staff were excellent on all occasions we spoke with them. The room was very rustic…real keys! Breakfast in the morning with coffee was nice and started the day off right. Our bed was a little lumpy that night."

Reviewed on Oct 5, 2026

Opens in a new windowThe Porches Inn at Mass MoCA
Willows Motel Williamstown

Willows Motel Williamstown

2 out of 5
480 Main St Williamstown MA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Nov 1 to Nov 2
$99 total
Nov 1 - Nov 2
Total with taxes and fees
This motel features a restaurant, an outdoor pool, and a poolside bar. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate ...
"The Willows was exactly what I needed for a last-minute trip to visit my son! The bed was fantastic, and the breakfast was full of beautiful fruit (so many different kinds of berries and melons), and farm-fresh eggs. (I generally skip free breakfasts because they're full of donuts, and was so grateful ..."

Reviewed on Oct 6, 2026

Opens in a new windowWillows Motel Williamstown
The White House Inn

The White House Inn

3.5 out of 5
178 Route 9 East Wilmington VT
$156 nightly
The price is $172 total per night from Nov 1 to Nov 2
$172 total
Nov 1 - Nov 2
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
"We loved this place! It was our first visit but oh so quaint. Loved the restaurant, fireplace in the room and all the wonderful siting areas around the property. It is a great place to recharge and watch the beautiful surroundings."

Reviewed on Oct 6, 2026

Opens in a new windowThe White House Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$119 nightly
The price is $133 total per night from Nov 1 to Nov 2
$133 total
Nov 1 - Nov 2
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 ...
"Great stay, very clean, super comfortable beds. Will def stay again when in the area."

Reviewed on Oct 6, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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
$169 nightly
The price is $186 total per night from Nov 5 to Nov 6
$186 total
Nov 5 - Nov 6
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. ...
"Allen in the restaurant is great."

Reviewed on Oct 6, 2026

Opens in a new windowGrand Summit Resort, A Vail Resorts Property
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $100 total per night from Oct 28 to Oct 29
$100 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features a seasonal outdoor pool and a hot tub. Enjoy the free ski shuttle and onsite ski storage. Enjoy the sauna and perks like free self parking ...
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received ..."

Reviewed on Oct 7, 2026

Opens in a new windowHideaway Inn Mt. Snow
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
$105 nightly
The price is $115 total per night from Nov 1 to Nov 2
$115 total
Nov 1 - Nov 2
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 ...
"We had a nice stay. Room was clean. The bathroom heat lamp was very nice!"

Reviewed on Oct 6, 2026

Opens in a new windowHotel Vervana, Trademark Collection by Wyndham
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
$174 nightly
The price is $194 total per night from Nov 4 to Nov 5
$194 total
Nov 4 - Nov 5
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 ...
Opens in a new windowThe Williams Inn
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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 $99. 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 1,010 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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

4 out of 5
Posted 17 hours ago
Travelocity Verified Review
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."
A verified traveler stayed at Hideaway Inn Mt. Snow
Hideaway Inn Mt. Snow

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