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
S$147
1 Nov - 2 Nov
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"The room was very spacious and clean. Staff was helpful, parking was easy. I would definitely stay here again."

Reviewed on 11 Oct, 2026

Hotel Vervana, Trademark Collection by Wyndham
Knotty Pine

Knotty Pine

130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
S$189
13 Oct - 14 Oct
includes taxes & fees
8.2/10 Very good! (178 reviews)
"I felt a little abandoned by the manager because she had very limite hours when she was available. The was pleasant and responsive when we did see her, but . . . Bathroom was clean and all, but design didn't allow space for a woman to lay out makeup and personal items. Very limited. Beds were very ..."

Reviewed on 7 Oct, 2026

Knotty Pine
Hampton Inn Bennington

Hampton Inn Bennington

51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
S$216
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The hotel is nearly complete with its renovation, therefore, a very new feel. It is a bit smaller than other Hampton Inns however convenient to reach. Our room was very clean the the staff was amazingly helpful! The breakfast was a bit limited in size however adequate. No microwave in our room."

Reviewed on 6 Oct, 2026

Hampton Inn Bennington
See all 811 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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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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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.
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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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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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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.