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
€96
3 Nov - 4 Nov
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"Older but well-maintained property. Rooms were clean and nice."

Reviewed on 21 Oct 2026

Hotel Vervana, Trademark Collection by Wyndham
New Englander Inn Bennington

New Englander Inn Bennington

220 Northside Drive Bennington VT
€89
25 Oct - 26 Oct
includes taxes & fees
7.6/10 Good! (1,002 reviews)
"Nice place and nice people running it. Full breakfast included. Nice bed but a bit too soft for us. Nice shower."

Reviewed on 22 Oct 2026

New Englander Inn Bennington
Hampton Inn Bennington

Hampton Inn Bennington

51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
€150
3 Nov - 4 Nov
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The hotel had just gone thru a remodel so everything was new and fresh. Accidentally left my phone behind and the employee walked me back up to the room to pick it up"

Reviewed on 19 Oct 2026

Hampton Inn Bennington
See all 822 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.
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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.
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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.
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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.
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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.
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Prospect Mountain Nordic Ski Center

8.6/10 (8 reviews)
Glide through 15 miles of pristine cross-country trails at this winter sports haven nestled in Vermont. Warm up in the welcoming lodge after exploring serene, snow-covered forests.
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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.
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Robert Frost Stone House Museum

9.2/10 (15 reviews)
You can spend an afternoon browsing the exhibits at Robert Frost Stone House Museum during your travels in Bennington. Discover the area's cosy cafes and its fascinating museums.
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What to do in Bennington

Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway

Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway

€22
per traveller
94% of travellers recommend
Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway
Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

€15
per traveller
80% of travellers recommend
Vermont RT 100 App-Guided Driving Audio Tour
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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.

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