
Bennington Vacations from $540
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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
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Manchester (MHT)
8.8/10 Excellent! (967 reviews)
This is a historic building with interesting architecture and it is nicely renovated inside keeping some of the charm of older days. It has a sprinkler system, fire alarm and smoke detector in the room. We originally paid for a supreme single queen room. When we arrived we were told we were "upgraded" to a king bed. It was on the 3rd floor with a small dormer window, most of which was blocked by a large TV screen. The window air conditioner was small due to the window size and it ran all night which is ok but it was very loud. We eventually turned it off to get a quiet sleep. The bed was very comfortable and the bathroom was spacious with fluffy towels, a large walk in shower that was all tiled with a glass partition. It was very nice with hot water but the tiles on the base of the shower needed a good scrubbing due to scale build up and what looked like black mold. The robes were soft and comfortable to lounge in. There was only one upholstered chair in a dark corner of the room so my husband sat on the office type desk chair to watch TV. I think I would have liked the original queen room better because the photo showed two large windows and the room appeared more spacious for two people. I purchased the room through Expedia so I'm not sure if that is why we were given the smaller room with sloping ceilings and shorter walls? Overall, this hotel is very clean and the bed was comfortable with plenty of pillows. I would recommend it but maybe not the 3rd floor dormer rooms.
Reviewed on Jul 28, 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 11 to Aug 12
$136 total
Aug 11 - Aug 12
Total includes taxes and fees
8.2/10 Very Good! (866 reviews)
"Staff are very nice. Free breakfast appreciated!"
Reviewed on Aug 3, 2025

Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $154 total per night from Aug 24 to Aug 25
$154 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,005 reviews)
"Great place!"
Reviewed on Jul 31, 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 7 to Aug 8
$205 total
Aug 7 - Aug 8
Total includes taxes and fees
8.6/10 Excellent! (1,001 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.