
Bennington Vacations from $344
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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.

Moultonborough Inn
Price was $460, price is now $344 per person
$344
per person
Oct 16 - Oct 20
found 17 hours ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9/10 Wonderful! (173 reviews)
Beds were great, everything is new. Kitchenette is convenient. Convenience store right next door.
I messaged that stairs are a problem and they called and emailed that we would be on the first floor. Not much room in the bathroom, only sink is part of kitchenette, but there is counter space for toiletries there.
Reviewed on Aug 11, 2025

Cold Spring Plymouth Resort
Save 100% on your flight
Price was $869, price is now $610 per person
$610
per person
Nov 1 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MHT)
9/10 Wonderful! (138 reviews)
2 night stay there was comfortable and convenient. Enjoyed the 2 days there. We didn't get to use the pool and gym room but we were given all the information about them. Would stay again .
Reviewed on Aug 25, 2025


Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG
Price was $725, price is now $608 per person
$608
per person
Nov 1 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MHT)
9.4/10 Exceptional! (1,000 reviews)
Great place with staff who care.
Reviewed on Aug 25, 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 Sep 3 to Sep 4
$136 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (882 reviews)
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash ..."
Reviewed on Aug 23, 2025

Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $170 total per night from Aug 31 to Sep 1
$170 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Clean, comfortable room, great breakfast & friendly staff."
Reviewed on Aug 17, 2025

Riverhouse by Weekender (Formerly Jack Daniels Inn)
80 Concord Street, Peterborough, NH
$130 nightly
The price is $141 total per night from Aug 31 to Sep 1
$141 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (416 reviews)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations."
Reviewed on Aug 13, 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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- Flights to Antrim
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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.