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.
Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
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

The Centennial

The Centennial

4 out of 5
Price was CA $1,744, price is now CA $1,260 per person
CA $1,260
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (989 reviews)
Not a large chain Old nursing home

Reviewed on Aug. 20, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was CA $2,167, price is now CA $1,845 per person
CA $1,845
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
9.6/10 Exceptional! (342 reviews)
It was in a beautiful area.

Reviewed on May 30, 2025

Four Points by Sheraton Bedford Manchester Airport

Four Points by Sheraton Bedford Manchester Airport

3 out of 5
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

Holiday Inn Express & Suites Merrimack by IHG

Holiday Inn Express & Suites Merrimack by IHG

2.5 out of 5
Price was CA $1,236, price is now CA $1,140 per person
CA $1,140
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (1,003 reviews)
Property was lovely.

Reviewed on Aug. 21, 2025

Ready to book your vacation to Bennington?

 

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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 $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

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 $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

Best Western Plus Keene Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
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

Riverhouse by Weekender (Formerly Jack Daniels Inn)
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
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Frequently asked questions

How much does a Bennington vacation package cost?
You'll find cheap prices from CA $1,080 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.