Book Hotels in Old Bennington, VT

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

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

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 Jan 26 to Jan 27
$271 total
Jan 26 - Jan 27
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 ...
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
$173 nightly
The price is $194 total per night from Jan 26 to Jan 27
$194 total
Jan 26 - Jan 27
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 pleasant and relaxing place to stay

Reviewed on Jan 3, 2026

Opens in a new windowThe Williams Inn
Chalet 239

Chalet 239

2 out of 5
239 Vermont Rte 100 West Dover VT
$188 nightly
The price is $207 total per night from Jan 15 to Jan 16
$207 total
Jan 15 - Jan 16
Total with taxes and fees
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also ...
It was great! Would stay here again, loved the TV and fiended when we saw there was a hot chocolate machine. Totally recommend, nice people and super close to the slopes so we could wake up late.

Reviewed on Dec 25, 2025

Opens in a new windowChalet 239
The White House Inn

The White House Inn

3.5 out of 5
178 Route 9 East Wilmington VT
$184 nightly
The price is $202 total per night from Jan 11 to Jan 12
$202 total
Jan 11 - Jan 12
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 ...
Staff was wonderful. Hotel is charming. Breakfast was great.

Reviewed on Dec 30, 2025

Opens in a new windowThe White House Inn
Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from Jan 9 to Jan 10
$118 total
Jan 9 - Jan 10
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like on-the-go breakfast and ...
Pet friendly, cooking was great plus, warm room

Reviewed on Jan 5, 2026

Opens in a new windowKnotty Pine
Big Bears Lodge

Big Bears Lodge

3 out of 5
344 Route 100 West Dover VT
$178 nightly
The price is $196 total per night from Jan 11 to Jan 12
$196 total
Jan 11 - Jan 12
Total with taxes and fees
This bed & breakfast features a seasonal outdoor pool and a hot tub. Free perks include cooked-to-order breakfast, free self parking, and a ski shuttle. Free ...
The owners were wonderful: kind, interesting to talk to, and very hospitable.

Reviewed on Oct 22, 2025

Opens in a new windowBig Bears Lodge
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$125 nightly
The price is $140 total per night from Feb 2 to Feb 3
$140 total
Feb 2 - Feb 3
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 ...
friendly accommodating staff

Reviewed on Jan 1, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
$336 nightly
The price is $369 total per night from Jan 13 to Jan 14
$369 total
Jan 13 - Jan 14
Total with taxes and fees
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi ...
Ski slopes were accessible and pool was really nice.

Reviewed on Dec 27, 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
$145 nightly
The price is $160 total per night from Jan 20 to Jan 21
$160 total
Jan 20 - Jan 21
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 ...
Friendly staff, value for money

Reviewed on Jan 1, 2026

Opens in a new windowValley Craft Ales
Don't see what you're looking for?
See all available properties in Old Bennington
View all properties
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 $118. 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 1,005 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

Explore More Ways to Travel with Travelocity