Bennington Vacations

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Find the Best Bennington Vacation Packages

Bennington Hotel Deals

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
The price is NT$3,804 per night from Jul 28 to Jul 29
NT$3,804
NT$4,147 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very Good! (1,015 reviews)
"Pool closed ! Advertise cool off after a day of hiking exploring,NOPE! No creamer for coffee in lobby, Ac couldn’t be adjusted controls didn’t work."

Reviewed on 2026/7/14

Hotel Vervana, Trademark Collection by Wyndham
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street Bennington VT
7.6/10 Good! (656 reviews)
"This property needs to be removed from the Expedia site. The photographs that it shows must’ve been taken about 50 years ago. The property is completely dilapidated and it looks as if it is possibly a halfway house for alcohol and drug abusers."

Reviewed on 2026/7/8

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The Autumn Inn
Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
The price is NT$3,505 per night from Jul 19 to Jul 20
NT$3,505
NT$3,821 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (114 reviews)
"We enjoyed the style of the Motel—brought back memories of long ago. It was impeccably clean and everything in the room was fine. We were only there one night but it was a very nice, reasonably priced by the night instead of 2-3 night mandatory we had seen. Staff was extremely friendly and welcoming ..."

Reviewed on 2026/7/12

Knotty Pine
See all 820 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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Frequently asked questions

How much does a Bennington vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation 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 neighborhoods like Old Bennington and South Shaftsbury during your Bennington vacation. 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 vacation package to Bennington?
Bennington is a good vacation 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 vacation 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," "Traveler 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 vacation as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalized vacation 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 vacation 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 accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Bennington vacation 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.