Bennington Vacations from $540

Book a Hotel + Flight or Car together to unlock savings

Your Bennington Vacation

With a vacation package to Bennington, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before departing, so you can enjoy each moment experiencing this interesting city. Every trip to Bennington needs a well-designed itinerary. Fill yours with big-name attractions like Crotched Mountain Ski and Ride Area, Peterborough Players and Greenfield State Park. Stop dreaming and start traveling. Check out the multitude of options on Expedia today and put your Bennington vacation plans into action!

The Latest Bennington vacation packages

Price found within the past 48 hours. Click for updated prices.
Riverside Hotel, Ascend Hotel Collection
Cold Spring Plymouth Resort
The Centennial
Anchor at Tideline
The Hotel Concord
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Bennington Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Aug 11 to Aug 12
$136 total
Aug 11 - Aug 12
Total includes taxes and fees
8.2/10 Very Good! (866 reviews)
"Staff are very nice. Free breakfast appreciated!"

Reviewed on Aug 3, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $154 total per night from Aug 24 to Aug 25
$154 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,005 reviews)
"Great place!"

Reviewed on Jul 31, 2025

Best Western Plus Keene Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St, Keene, NH
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $205 total per night from Aug 7 to Aug 8
$205 total
Aug 7 - Aug 8
Total includes taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Property in good condition, clean, well located in Keene."

Reviewed on Aug 1, 2025

Courtyard by Marriott Keene Downtown
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.

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Frequently asked questions

How much does a Bennington vacation package cost?
You can grab a vacation package to this top destination from $540 on Expedia. But how much your vacation to Bennington costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Bennington?
You can generally find lower prices and better availability in October, November and December. Browse our cheap Bennington vacation packages and you could land some great off-season discounts.
How many days is enough for Bennington?
Typically, a handful of days is enough to explore the top sights during your Bennington vacation. But if you want to have time to unwind or take day trips, think about extending your itinerary.
How to find the best Bennington package deals?
Use Expedia's filters to help you find some tempting Bennington package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Bennington package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Bennington vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Bennington vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Bennington?
If you're planning a spontaneous Bennington trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Bennington vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Bennington vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.