Bennington Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $1,330, price is now CA $1,074 per person
CA $1,074
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Lovely and very helpful staff - Late night and early morning! Bed was very comfortable and breakfast was out early and very nice.
Reviewed on Apr 6, 2026
The Lake Estate on Winnisquam
Price was CA $1,974, price is now CA $1,584 per person
CA $1,584
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
9.6/10 Exceptional! (15 reviews)
Exceptional place beautiful landscape and very relaxing
Reviewed on May 10, 2026
Cold Spring Plymouth Resort
Price was CA $1,376, price is now CA $1,147 per person
CA $1,147
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Manchester (MHT)
9.2/10 Wonderful! (209 reviews)
The property is good for skying in the area. Nothing fancy, but works perfectly for families who are out all day.
Reviewed on Apr 19, 2026
Bennington Hotel Deals
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Bennington NH
The price is CA $197 per night from May 25 to May 26
CA $197
CA $445 total
May 25 - May 26
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 $211 per night from May 17 to May 18
CA $211
CA $229 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Breakfast was only till 9:30 and some of the food was dried out. The room was clean and service was great.. we enjoyed the restaurant attached. Staff was wonderful
Reviewed on May 12, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from May 26 to May 27
CA $192
CA $208 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
The hotel room was exceptionally clean and well maintained. The bed linens and bathroom were spotless, and the entire room smelled fresh upon arrival.
Reviewed on May 12, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
