Bennington Vacations from $434

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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 $527, price is now $434 per person
$434
per person
Jan 1 - Jan 3
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
The staff were great. The room was clean and nice. We had a window problem that was corrected quickly. Toiletries were fine. The only reason for a 4 rating is the continental breakfast was not good - the bagels, muffins & pastry were stale and the coffee was not good. It was a great location. Unfortunately many stores and restaurants were closed on Sundays & Mondays, not the hotel’s fault something to note if visiting Concord NH.

Reviewed on Nov 18, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $729, price is now $622 per person
$622
per person
Jan 1 - Jan 3
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
9.6/10 Exceptional! (352 reviews)
Beautiful place to stay.

Reviewed on Nov 26, 2025

Tru by Hilton Concord

Tru by Hilton Concord

2.5 out of 5
Price was $579, price is now $509 per person
$509
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
8/10 Very Good! (833 reviews)
The room and public areas were very clean. The breakfast offered a good variety of food. All of the staff were courteous and friendly.

Reviewed on Nov 17, 2025

Perry's Motel and Cottages

Perry's Motel and Cottages

2.5 out of 5
Price was $966, price is now $853 per person
$853
per person
Feb 16 - Feb 20
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Manchester (MHT)
8.4/10 Very Good! (370 reviews)
Messy surroundings . No breakfast to speak of. Room was spacious and clean.

Reviewed on Nov 20, 2025

Fairfield Inn & Suites by Marriott Hooksett

Fairfield Inn & Suites by Marriott Hooksett

2.5 out of 5
Price was $480, price is now $440 per person
$440
per person
Jan 1 - Jan 3
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
9/10 Wonderful! (753 reviews)
Breakfast changed a bit daily with lots of options. It was the best included breakfast at this level of hotel that we've ever had!

Reviewed on Nov 12, 2025

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Bennington Hotel Deals

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
$147 nightly
The price is $160 total per night from Dec 23 to Dec 24
$160 total
Dec 23 - Dec 24
Total with taxes and fees
8.8/10 Excellent! (348 reviews)
Beautiful room. Breakdadt was good, staff very friendly

Reviewed on Nov 19, 2025

Hampton Inn & Suites Keene
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 refundable
$109 nightly
The price is $118 total per night from Dec 17 to Dec 18
$118 total
Dec 17 - Dec 18
Total with taxes and fees
8.4/10 Very Good! (951 reviews)
Perfect spot for a quick overnight- clean and conveniently located!

Reviewed on Nov 22, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
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
$139 nightly
The price is $151 total per night from Nov 27 to Nov 28
$151 total
Nov 27 - Nov 28
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
I received accommodations from Sarah of the hotel staff that were above and beyond my expectations. My colleague and I were travelling for work and we accidentally both booked rooms for the night. Sarah was able to cancel my colleague's reservation for with no hassle whatsoever. Thank you Sarah!

Reviewed on Nov 17, 2025

Best Western Plus Keene Hotel
See all 302 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

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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 $434 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.

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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.