Bennington Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
Quality Inn Merrimack - Nashua

Quality Inn Merrimack - Nashua

2.5 out of 5
Price was CA $1,198, price is now CA $1,198 per person
CA $1,198
per person
Nov 27 - Nov 29
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
7.8/10 Good! (1,004 reviews)

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was CA $1,734, price is now CA $1,651 per person
CA $1,651
per person
Nov 27 - Nov 30
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
9.6/10 Exceptional! (401 reviews)

Hotel Coolidge

Hotel Coolidge

3 out of 5
Price was CA $1,233, price is now CA $1,207 per person
CA $1,207
per person
Nov 27 - Nov 29
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.2/10 Very good! (1,002 reviews)

Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
Price was CA $1,226, price is now CA $1,203 per person
CA $1,203
per person
Nov 27 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.6/10 Excellent! (1,005 reviews)
Friendly staff, nice room and bathroom. Good breakfast. Parking was limited or difficult to find a space in the evening.

Reviewed on Oct 26, 2026

Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
Price was CA $1,256, price is now CA $1,256 per person
CA $1,256
per person
Nov 27 - Nov 29
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.4/10 Very good! (1,001 reviews)
Quick to check in and clean room.

Reviewed on Oct 25, 2026

Ready to book your vacation to Bennington?

 

Choose your dates

Bennington Hotel Deals

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Bennington NH
The price is CA $276 per night from Nov 18 to Nov 19
CA $276
CA $560 total
Nov 18 - Nov 19
includes taxes & fees
10/10 Exceptional! (16 reviews)
"It was exactly as described and very private. We had a couple issues but communication was good and everything was sorted out."

Reviewed on Oct 1, 2026

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
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 $198 per night from Nov 4 to Nov 5
CA $198
CA $215 total
Nov 4 - Nov 5
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"Breakfast was exceptional. Lori keeps everything clean and organized. We have never been to a hotel breakfast that comes close."

Reviewed on Oct 26, 2026

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

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Oct 28 to Oct 29
CA $185
CA $201 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"."

Reviewed on Oct 26, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
See all 334 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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Bennington vacation package cost?
You'll find cheap prices from CA $1,198 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.