Old Bennington Vacation Packages

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Your Old Bennington Vacation

The rich history and spectacular views are just the start of the things Old Bennington has on offer. Experience the very best of this interesting city the way you want with a personalized Old Bennington vacation package. If your trip to Old Bennington includes a little sightseeing, check out famous attractions like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Expedia will help you escape the everyday. Tailor your vacation to Old Bennington to suit your travel style, whatever that may look like.

Top Old Bennington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $890, price is now CA $717 per person
CA $717
per person
Oct 12 - Oct 16
just found
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,015 reviews)
Great location. Very clean.

Reviewed on Jul 23, 2026

The Whitlock

The Whitlock

2 out of 5
Price was CA $1,334, price is now CA $1,022 per person
CA $1,022
per person
Oct 12 - Oct 16
just found
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very good! (332 reviews)
Very nice coffee set up in the morning. Staff was super courteous and helpful. Most of property is updated although carpeting and rugs are tired. Location is great, very convenient to Tanglewood and restaurants. Parking is onsite and more than ample. B

Reviewed on Jul 25, 2026

Gedney Farm

Gedney Farm

3.5 out of 5
Price was CA $1,312, price is now CA $1,014 per person
CA $1,014
per person
Oct 12 - Oct 16
just found
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (138 reviews)
Pet friendly and amazing grounds

Reviewed on Jul 17, 2026

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $911, price is now CA $725 per person
CA $725
per person
Oct 12 - Oct 16
just found
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,463 reviews)
It was a nice room with a beautiful location, and the pools were well maintained. However, the front desk was repeatedly grumpy whenever we had a question. Even saying good morning was met with an indifferent tone. For example, the washer didn't work (rinse cycle didn't work) and when I reported it in order to help the next person who would use it, they didn't seem interested and were put off. Additionally, the keys consistently didn't work until after several times, and whenever we tried to call the front desk for fresh towels the line would disconnect. The arcade also didn't work since the tickets wouldn't print after depositing money.

Reviewed on Jul 24, 2026

Berkshires Untold

Berkshires Untold

3.5 out of 5
Price was CA $1,113, price is now CA $917 per person
CA $917
per person
Oct 12 - Oct 16
just found
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,018 reviews)

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Old Bennington Hotel Deals

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
The price is CA $360 per night from Aug 5 to Aug 6
CA $360
CA $393 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (290 reviews)
"Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar"

Reviewed on Jul 24, 2026

The Four Chimneys Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is CA $242 per night from Aug 16 to Aug 17
CA $242
CA $271 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Loved this hotel. I can't rate it highly enough. Highly recommend."

Reviewed on Jul 25, 2026

Hotel Downstreet, an Ascend Collection Hotel
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
The price is CA $701 per night from Aug 24 to Aug 25
CA $701
CA $1,200 total
Aug 24 - Aug 25
includes taxes & fees
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on May 25, 2026

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
See all 1,012 properties in Old 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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Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the coffeehouses and its art scene while you're in the area.
See properties

What to do in Old Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington

Frequently asked questions

How much does an Old Bennington vacation package cost?
Offering great value package deals from CA $717 on Expedia, you'll be thrilled with how little a vacation to Old Bennington costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Old Bennington?
If you'd like to book a cheap Old Bennington vacation package, consider visiting in January, March and August. You'll generally find lower rates on accommodations and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Old Bennington?
Usually, a handful of days is enough to go to the major attractions during your Old Bennington vacation. However, if you want to have some time to relax or take day trips, think about extending your trip.
How to find the best Old Bennington package deals?
Bagging a cheap Old Bennington package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Old Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Old Bennington vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights separately. Better still, you can customize your Old Bennington trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Old Bennington?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Old Bennington trip.
How to plan a trip to Old Bennington?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Old Bennington.
  2. Budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Old Bennington.
  3. Decide how long to go away for: Now that you're up to speed on Old Bennington, you can figure out the perfect length of your vacation. Put together a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose an Old 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.