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.
Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Price was CA $2,264, price is now CA $1,597 per person
CA $1,597
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
I had a pleasant stay with my dogs. The hotel is older but clean, has friendly staff, great pet policy with no pet fees, great breakfast, a convenient location near Conway, beautiful views, and a peaceful atmosphere.

Reviewed on Jun 26, 2026

Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Price was CA $2,522, price is now CA $1,610 per person
CA $1,610
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Manchester (MHT)
8.8/10 Excellent! (1,004 reviews)
Gorgeous property, attentive staff, and very comfortable bed.

Reviewed on Jun 27, 2026

Eastern Slope Inn Resort

Eastern Slope Inn Resort

3 out of 5
North Conway Village
Price was CA $2,374, price is now CA $1,670 per person
CA $1,670
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Manchester (MHT)
8.8/10 Excellent! (462 reviews)
It was more than what I expected. Great kitchen facilities, wonderful location. Most relaxing mini vacation ever!

Reviewed on Jun 29, 2026

Tiny Home Topline

Tiny Home Topline

2 out of 5
Price was CA $12,361, price is now CA $8,992 per person
CA $8,992
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Manchester (MHT)
No reviews

Attitash Mountain Village

Attitash Mountain Village

3 out of 5
Price was CA $2,377, price is now CA $1,732 per person
CA $1,732
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Manchester (MHT)
8.6/10 Excellent! (563 reviews)

Ready to book your vacation to Bennington?

 

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Bennington Hotel Deals

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 $155 per night from Jul 14 to Jul 15
CA $155
CA $168 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"It was clean staff was nice friendly and dressed in uniforms breakfast nice breakfast area was clean i would stay at ascend collection hotel again.. i wish would have done so near bar harbor area but didnt"

Reviewed on Jun 29, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
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 $181 per night from Jul 6 to Jul 7
CA $181
CA $196 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"It was average but not worth the cost"

Reviewed on Jun 30, 2026

Best Western Plus Keene Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
The price is CA $255 per night from Jul 15 to Jul 16
CA $255
CA $277 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Very clean, well run, hotel. No complaints. Staff was very helpful and friendly"

Reviewed on Jun 29, 2026

Courtyard by Marriott Keene Downtown
See all 327 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.
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Frequently asked questions

How much does a Bennington vacation package cost?
You'll find cheap prices from CA $1,597 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.

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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.