Bennington Vacation Packages
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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.
The Centennial
Price was CA $1,964, price is now CA $1,539 per person
CA $1,539
per person
Jun 10 - Jun 17
found 4 hours ago
Roundtrip flight included
Montreal (YMQ) to Manchester (MHT)
8.8/10 Excellent! (1,003 reviews)
Room and bathroom were great; bed / pillows so comfortable; love the robes. Breakfast had just the right amount of variety / selections.
Elevator was not working but we were ok with stairs. It had been not working in our December visit either.
Reviewed on Mar 22, 2026
The Grand at Bedford Village Inn
Price was CA $3,147, price is now CA $2,662 per person
CA $2,662
per person
Jun 10 - Jun 17
found 4 hours ago
Roundtrip flight included
Montreal (YMQ) to Manchester (MHT)
9.6/10 Exceptional! (360 reviews)
Everything was above and beyond. Our room was lovely. Every staff member was great! I would highly recommend the BVI.
Reviewed on Jan 29, 2026
Holiday Inn Express & Suites Merrimack – Nashua by IHG
Price was CA $1,198, price is now CA $1,071 per person
CA $1,071
per person
Jun 10 - Jun 17
found 4 hours ago
Roundtrip flight included
Montreal (YMQ) to Manchester (MHT)
8.8/10 Excellent! (1,007 reviews)
The pool is an outdoor pool so closing winter and.no hot tub. Rooms were clean and quiet. Breakfast buffet had a share of heavy foods and fruits and yogurts so there are options. Easy parking.
Reviewed on Mar 22, 2026
Bennington Hotel Deals
Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking
Bennington NH
The price is CA $254 per night from Apr 1 to Apr 2
CA $254
CA $520 total
Apr 1 - Apr 2
includes taxes & fees
10/10 Exceptional! (12 reviews)
Great spot! Perfect location for our ski weekend at Crotched!
Reviewed on Mar 14, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Mar 31 to Apr 1
CA $214
CA $232 total
Mar 31 - Apr 1
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Room was fine. Only stayed one night for a quick trip. Didn't realize that the restaurant was closed on Sundays. Was looking for a meal after a long drive, but there were plenty of places to eat in the area.
Reviewed on Mar 24, 2026
Courtyard by Marriott Keene Downtown
75 Railroad St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $250 per night from Apr 5 to Apr 6
CA $250
CA $271 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Quiet and convenient location. Loved having a microwave in my room. I wasn't in the mood for wating out so a trip to the neighbouring supermarket set me up perfectly.
Reviewed on Mar 13, 2026
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.