Bennington Holidays
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Bennington Holiday
Our pick of the best Bennington Hotel Deals
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
NZ$204
30 Aug - 31 Aug
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"The staff was great and welcoming. The room was comfortable and clean. The shower was strong and wonderful. The hotel was walking distance to pubs and restaurants. Overall a great night."
Reviewed on 14 Aug 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
NZ$201
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very good! (136 reviews)
"Rooms are a good size, beds are comfortable."
Reviewed on 16 Aug 2026
New Englander Inn Bennington
220 Northside Drive Bennington VT
Fully refundableReserve now, pay when you stay
NZ$195
23 Aug - 24 Aug
includes taxes & fees
7.6/10 Good! (989 reviews)
"Stairwell needs cleaning, but very comfortable and good value for the price."
Reviewed on 13 Aug 2026
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.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
8.6/10 (18 reviews)
This vintage Sunoco station houses an impressive collection of classic cars for free viewing. Browse automotive memorabilia in the Car Lover's Store or visit summer Thursday Cruise-ins to mingle with fellow enthusiasts.
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.
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.
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.
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.
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.
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.
What to do in Bennington
Vermont RT 100 App-Guided Driving Audio Tour
NZ$29
per traveller
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?
- 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.
- 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.
- 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.
- Combine your accommodation and airfare: After you've nailed down your travel dates and duration, book the ideal Bennington holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
