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.
Four Points by Sheraton Bedford Manchester Airport

Four Points by Sheraton Bedford Manchester Airport

3 out of 5
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Manchester (MHT)
9/10 Wonderful! (61 reviews)
It was a quick night stay because my husband was having an early morning surgery. We got in very late and left early, but everything we saw was clean and looked like it was recently renovated. The front desk staff was friendly and quick and informative. I would definitely stay here again.

Reviewed on Aug. 7, 2025

Garner Hotel Londonderry - Manchester by IHG

Garner Hotel Londonderry - Manchester by IHG

2.5 out of 5
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Manchester (MHT)
8.6/10 Excellent! (1,003 reviews)
Around 10 pm the peroson in the room next door to me decided to try an open my adjoining door to their room. Once i screamed they stopped. The toilet would run constantly until you fiddled with the handle.

Reviewed on Aug. 3, 2025

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Bennington Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Aug 14 to Aug 15
CA $172
CA $187 total
Aug 14 - Aug 15
includes taxes & fees
8.4/10 Very Good! (871 reviews)
"Is a very well cared for hotel and I enjoyed my stay and I’ve stayed there several times."

Reviewed on Aug. 5, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Aug 24 to Aug 25
CA $195
CA $211 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Attention to detail
"We were completely stunned with how wonderful this hotel was from top to bottom. The staff was very friendly and accommodating (they let us have a 1 hour late check out with no charge), the breakfast was fantastic (best I’d ever had in a hotel that offers it free), it was extremely clean, and the ..."

Reviewed on Aug. 6, 2025

Best Western Plus Keene Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $260 per night from Aug 24 to Aug 25
CA $260
CA $282 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Property in good condition, clean, well located in Keene."

Reviewed on Aug. 1, 2025

Courtyard by Marriott Keene Downtown
See all 304 properties in Bennington
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Bennington vacation package cost?
You'll find cheap prices from CA $976 on Expedia for your Bennington escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Bennington costs.
What are the cheapest months to go to Bennington?
The off-season is the best time to visit Bennington if you're trying to save. Another tip for getting cheap Bennington vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Bennington?
With a well-organized travel plan, you can easily tick off the top Bennington sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Bennington vacation for longer.
How to find the best Bennington package deals?
Start your search for a Bennington package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Bennington package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Bennington escape off to a flying start.
Is it cheaper to book a Bennington vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Bennington vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Bennington?
If you're planning a spur-of-the-moment Bennington vacation, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Bennington?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the type of activities on offer will also help you decide when to escape to Bennington.
  2. Set a budget: Consider expenses like flights, meals and transportation when calculating how much to put aside for your trip to Bennington. Then, choose a hotel that works with your budget, whether that's a wallet-friendly option or a lavish getaway.
  3. Determine how many days away: Start by compiling a list of the activities and sights you'd like to get to in Bennington. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the right Bennington vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.