
Bennington Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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!
Top Bennington Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hampton Inn & Suites Manchester-Bedford
Price was CA $1,175, price is now CA $1,080 per person
CA $1,080
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.4/10 Very Good! (1,003 reviews)
The beds were comfortable
Carpeting in the halls were dirty
Reviewed on Aug. 17, 2025



Four Points by Sheraton Bedford Manchester Airport
Price was CA $1,301, price is now CA $1,179 per person
CA $1,179
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (84 reviews)
Great room for the price, microwave and refrigerator and Netflix plus other streaming options. Very nice accommodations!!!
Reviewed on Aug. 14, 2025
Bennington Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Aug 31 to Sep 1
CA $174
CA $189 total
Aug 31 - Sep 1
includes taxes & fees
8.4/10 Very Good! (881 reviews)
"Had a great time at this location"
Reviewed on Aug. 19, 2025

Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 24 to Aug 25
CA $207
CA $225 total
Aug 24 - Aug 25
includes taxes & 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
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Aug 31 to Sep 1
CA $148
CA $175 total
Aug 31 - Sep 1
includes taxes & 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.