Bennington Holidays

Top hotels in Bennington

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
€103
14 Sept - 15 Sept
includes taxes & fees
Hotel Vervana, Trademark Collection by Wyndham
Knotty Pine

Knotty Pine

130 Northside Dr Bennington VT
€118
15 Sept - 16 Sept
includes taxes & fees
8.4/10 Very good! (156 reviews)
"The room was what we needed for the weekend. We didn’t spend a lot of time there, we were vendors at the Bennington garlic festival. But, we got a good night sleep and it was very comfortable."

Reviewed on 6 Sept 2026

Knotty Pine
Bennington Motor Inn

Bennington Motor Inn

143 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
€79
9 Sept - 10 Sept
includes taxes & fees
7.6/10 Good! (492 reviews)
"Very clean and cozy."

Reviewed on 7 Sept 2026

Bennington Motor Inn
See all 813 properties in Bennington
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.

Stay near popular Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
This 306-foot obelisk commemorates a pivotal Revolutionary War battle and stands as Vermont's tallest structure. Ascend to the observatory for breathtaking views spanning Vermont, Massachusetts, and New York.
See properties

Southern Vermont College

8.2/10 (22 reviews)
Explore the historic Everett Mansion on the former Southern Vermont College campus with its striking architecture. Wander the 371-acre grounds for breathtaking views of the Green Mountains in this peaceful setting.
See properties

Bennington Museum

9.0/10 (50 reviews)
Home to the world's largest public collection of Grandma Moses paintings, this museum celebrates Vermont's cultural heritage. Explore Revolutionary War artefacts and view the galleries.
See properties

Woodford State Park

8.8/10 (11 reviews)
Vermont's highest campground at 2,400 feet, Woodford State Park surrounds pristine Adams Reservoir. Explore the lakeside trail through forests or rent a boat to fish for brook trout in this mountain sanctuary.
See properties

Bennington Center for the Arts

8.6/10 (22 reviews)
This cultural hub showcases diverse art exhibitions, Native American works, and Vermont's heritage through its Covered Bridge Museum. Explore multiple galleries and surrounding gardens for a complete artistic immersion.
See properties

Prospect Mountain Cross-Country Ski Center

9.0/10 (28 reviews)
Vermont's highest-based Nordic ski centre offers over 30 kilometres of groomed trails for all skill levels. Warm up by the stone fireplace in the cosy lodge after conquering the pristine mountain routes.
See properties

Bennington Potters Yard

8.0/10 (11 reviews)
Watch skilled artisans shape clay into beautiful stoneware at this historic pottery workshop dating back to 1948. Tour the factory floor to witness the crafting process before browsing finished pieces.
See properties

Old First Congregational Church

9.6/10 (12 reviews)
This 1805 Palladian church houses the final resting place of poet Robert Frost and several Vermont governors. Wander through the elegant interior and serene cemetery for a glimpse into Bennington's rich history.
See properties

Frequently asked questions

How much does a Bennington holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Bennington costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bennington?
You can generally find lower prices and greater availability in January, March and November. Browse our cheap Bennington holiday packages and you could land some great off-season discounts.
How many days is enough for Bennington?
With about 2 days, you'll have plenty of time to experience popular neighbourhoods like Old Bennington and South Shaftsbury during your Bennington holiday. Remember to also add Norman Rockwell Exhibition and Robert Frost Stone House Museum to your list of must-sees. Looking for more adventures? Consider venturing outside of Bennington on day trips and tours.
Is it worth booking a holiday package to Bennington?
Bennington is a good holiday destination with attractions like Bennington Battle Monument among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Bennington holiday promises a good time for everyone.
How to find the best Bennington package deals?
Finding a cheap Bennington package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bennington holiday as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Bennington?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Bennington adventure.
How to plan a trip to Bennington?
  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Bennington.
  2. Plan your budget wisely: As well as the price of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may arise during your trip to Bennington.
  3. Decide how long to go for: Now that you're more familiar with Bennington, you can figure out the right length of your break. Create a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your accommodation and airfare: After you've nailed down your travel dates and duration, book the ideal Bennington holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.