Bennington Vacations from $446

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.
The Centennial

The Centennial

4 out of 5
Price was $593, price is now $446 per person
$446
per person
Mar 19 - Mar 23
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Loved the small, cozy atmosphere

Reviewed on Dec 26, 2025

Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Price was $721, price is now $469 per person
$469
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Manchester (MHT)
7.6/10 Good! (1,000 reviews)
Perfectly fine for a quick stay and great price. WiFi didn’t work in room, otherwise, clean, hot shower, comfortable bed and pillows. Dining options within 15 minutes

Reviewed on Nov 11, 2025

Cranmore Mountain Lodge Bed & Breakfast

Cranmore Mountain Lodge Bed & Breakfast

3 out of 5
Kearsarge
Price was $833, price is now $624 per person
$624
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Manchester (MHT)
8.8/10 Excellent! (244 reviews)
Adorable air bnb, off the beaten path from downtown, quiet and very charming. Loved sitting on the porch surrounded by all the fall colors. Host was friendly and welcoming. Breakfast was yummy. Has a great New England charm and very cozy. Will definitely be back.

Reviewed on Oct 29, 2025

Sunset Hill House

Sunset Hill House

4 out of 5
Price was $766, price is now $576 per person
$576
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Room was spectacular, everything was clean, staff was helpful and friendly. The views were amazing

Reviewed on Dec 24, 2025

The Chandler Inn Bethlehem - Littleton, an Ascend Collection Hotel

The Chandler Inn Bethlehem - Littleton, an Ascend Collection Hotel

3 out of 5
Price was $794, price is now $600 per person
$600
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Manchester (MHT)
8.4/10 Very Good! (689 reviews)
Very clean rooms & the staff was very friendly

Reviewed on Dec 23, 2025

Don't see what you're looking for?
See all available trips from Columbus to Bennington
View all trips

Bennington Hotel Deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $135 total per night from Dec 29 to Dec 30
$135 total
Dec 29 - Dec 30
Total with taxes and fees
8.4/10 Very Good! (966 reviews)
The room was perfect, and the food was great

Reviewed on Dec 15, 2025

Keene Elm City Hotel, an Ascend Collection 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
$180 nightly
The price is $195 total per night from Jan 3 to Jan 4
$195 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
looks good

Reviewed on Dec 16, 2025

Courtyard by Marriott Keene Downtown
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $181 total per night from Jan 25 to Jan 26
$181 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
8.8/10 Excellent! (358 reviews)
2

Reviewed on Dec 23, 2025

Hampton Inn & Suites Keene
See all 295 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.

Find the Best Bennington Vacation Packages

Bennington Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
380
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Crotched Mountain Ski and Ride Area, Peterborough Players and Greenfield State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Bennington vacation package cost?
You can grab a vacation package to this top destination from $446 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.

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.