Bennington Vacations from $553
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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
per person
Oct 28 - Nov 2
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Manchester (MHT)
8.8/10 Excellent! (977 reviews)
Room was very spacious
Cute New England Victorian vibe
Clean
Bed was comfortable
Breakfast included
Smart tv
Restaurant inside hotel
Reviewed on Aug 10, 2025
Bennington Hotel Deals
Keene Elm City Hotel, Ascend Hotel Collection
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Aug 20 to Aug 21
$136 total
Aug 20 - Aug 21
Total includes taxes and fees
8.4/10 Very Good! (876 reviews)
"Hotel was very clean, and staff was extraordinarily good!"
Reviewed on Aug 10, 2025
Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Aug 14 to Aug 15
$162 total
Aug 14 - Aug 15
Total includes taxes and fees
8.2/10 Very Good! (1,002 reviews)
Attention to detail
"We were completely stunned with how wonderful this hotel was from top to bottom. The staff was very friendly and accommodating (they let us have a 1 hour late check out with no charge), the breakfast was fantastic (best I’d ever had in a hotel that offers it free), it was extremely clean, and the ..."
Reviewed on Aug 6, 2025
Courtyard by Marriott Keene Downtown
75 Railroad St, Keene, NH
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $205 total per night from Aug 18 to Aug 19
$205 total
Aug 18 - Aug 19
Total includes taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Property in good condition, clean, well located in Keene."
Reviewed on Aug 1, 2025
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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- Hotels near Crotched Mountain Ski and Ride Area
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- Crotched Mountain Ski and Ride Area
- Visit Antrim
- Hancock Vacations
- Visit Hancock
- Visit Greenfield
- Harris Center for Conservation Education
- Visit Francestown
- Peterborough Players
- Eaton's Magic Morsel
- Hillsboro Vacations
- Sharon Arts Center
- Mariposa Museum and World Cultures Center
- Franklin Pierce Homestead
- Peterborough Town House
- The Monadnock Center for History and Culture
- Visit Hillsboro
- Visit Peterborough
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.