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$3,544 per night from Aug 31 to Sep 1
NT$3,544
NT$3,863 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Love this place"

Reviewed on 2025/8/15

Hotel Vervana, Trademark Collection by Wyndham
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is NT$3,454 per night from Aug 28 to Aug 29
NT$3,454
NT$3,765 total
Aug 28 - Aug 29
includes taxes & fees
7.6/10 Good! (882 reviews)
"The bed was the most comfortable ever. The pool was crystal clear and the breakfast was good. The clientele were very friendly and accommodating. Nice place!"

Reviewed on 2025/8/17

Best Western Bennington
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
The price is NT$2,670 per night from Aug 31 to Sep 1
NT$2,670
NT$2,910 total
Aug 31 - Sep 1
includes taxes & fees
7.6/10 Good! (598 reviews)
"I’ve said it before just wonderful people and place."

Reviewed on 2025/8/16

The Autumn Inn
See all 740 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.

Discover the most popular places to visit in Bennington

Bennington Battle Monument showing landscape views

Bennington Battle Monument

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

Prospect Mountain Cross-Country Ski Center

Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.

Prospect Mountain Cross-Country Ski Center

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.

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