Bennington Vacation Packages

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Your Bennington Vacation

Our vacation packages to Bennington allow you to create your own adventure. Tailor your getaway to your interests and needs and make every moment count in this interesting city. Every trip to Bennington needs a well-planned itinerary. Fill yours with famous sights like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Don't put off visiting this city any longer. The ultimate Bennington vacation is only a few clicks away with Expedia.

Top Bennington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
South Shire

South Shire

4 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (92 reviews)
Cute place to stay walking distance from brewery.

Reviewed on Jul. 25, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (504 reviews)
My husband and I stayed one night to celebrate our anniversary. The room was clean, roomy and comfortable. The hotel is huge in a beautiful surrounding with many activities included in the price. Swimming, bike riding and an easy drive into the main town. We would recommend the Equinox and plan on returning in the future for several nights.

Reviewed on Aug. 6, 2025

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (782 reviews)
Great location, nice front porch. Nice bar. There is no gym, breakfast, snacks, or gift shop, however, a clothing boutique is available. As a pet-friendly hotel, oftentimes I was interrupted by dogs barking and growling at each other - I felt I was at a kennel. Value for the room rate was underwhelming.

Reviewed on Jul. 24, 2025

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.6/10 Exceptional! (1,003 reviews)
We really enjoyed our stay at this property. It's nicely kept.. and EV charging is included in stay. Great breakfast, too.

Reviewed on Aug. 4, 2025

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Bennington Hotel Deals

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Aug 17 to Aug 18
CA $138
CA $150 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (999 reviews)
Quiet, relaxing hotel
"Room was spacious. Bed was comfortable. Building was quiet. Wifi was fast and stable. Very relaxing environment. I would definitely come back to see what future improvements are made to the property as I was told by the front desk staff that they're making a constant effort to upgrade the ..."

Reviewed on Aug. 5, 2025

Hotel Vervana, Trademark Collection by Wyndham
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 10 to Aug 11
CA $122
CA $133 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (593 reviews)
good bed
"Have stayed here before overall conditions were good convenient for my visit biggest determining factor for me was the availability of a king size bed which as it turned out was quite comfortable"

Reviewed on Aug. 4, 2025

The Autumn Inn
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Aug 14 to Aug 15
CA $158
CA $172 total
Aug 14 - Aug 15
includes taxes & fees
7.6/10 Good! (868 reviews)
"Great customer service. Perfect spot for a berkshires getaway"

Reviewed on Jul. 20, 2025

Best Western Bennington
See all 738 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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What to do in Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

CA $23
per traveller
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Bennington

Frequently asked questions

How much does a Bennington vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,682 on Expedia. But how much your vacation to Bennington costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Bennington?
January, March and November are great times to search for cheap Bennington vacation packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and hotels.
How many days is enough for Bennington?
To get the most out of your Bennington vacation, we suggest staying for 2 days. Divide your time between visiting Bennington Centre for the Arts, Old First Congregational Church and other leading sights, as well as experiencing neighbourhoods like Old Bennington and South Shaftsbury. If you've got some spare time, include a day trip in your Bennington vacation itinerary.
Is it worth booking a vacation package to Bennington?
Bennington has everything you need for an amazing escape. Get your Bennington vacation off to a flying start by checking out major attractions like Bennington Battle Monument.
How to find the best Bennington package deals?
Use Expedia's filters to help you find some great Bennington package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Bennington package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Bennington vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can customize your Bennington escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Bennington?
If you're considering a spontaneous Bennington adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Bennington?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Bennington.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will likely be the biggest expense during your trip to Bennington.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Bennington. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Bennington vacation package that brings all your bookings together.

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