Bennington Vacation Packages

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Top Bennington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Louisville Airport

Hilton Garden Inn Louisville Airport

3 out of 5
Fairgrounds
Price was CA $1,204, price is now CA $895 per person
CA $895
per person
Sep 29 - Oct 3
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
Nice spacious rooms with comfy beds. Not a lot of food options for breakfast

Reviewed on Aug. 10, 2025

Hyatt Regency Cincinnati

Hyatt Regency Cincinnati

4 out of 5
Downtown Cincinnati
Price was CA $1,900, price is now CA $1,304 per person
CA $1,304
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9/10 Wonderful! (1,497 reviews)
I had an amazing stay here! The staff were amazing! This is my first trip to Cincinnati and I loved every bit of it, but the staff here made it that much better! Special shout out to Brandon, Scott, and my beautiful waitress! I am not going to butcher her name, but she was very attentive, personable, and kind. The valet staff were all so courteous! I just knew Adam got sick of me going to get my keys every 5 minutes, but he was so pleasant anyway. All in all, great place to stay and the people are amazing.

Reviewed on Aug. 25, 2025

21c Museum Hotel Cincinnati

21c Museum Hotel Cincinnati

4.5 out of 5
Downtown Cincinnati
Price was CA $1,960, price is now CA $1,475 per person
CA $1,475
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
8.8/10 Excellent! (1,010 reviews)
The hotel was a museum

Reviewed on Aug. 19, 2025

The Summit Hotel

The Summit Hotel

4 out of 5
Price was CA $2,015, price is now CA $1,542 per person
CA $1,542
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9.2/10 Wonderful! (1,000 reviews)
We were in there for the Cincinnati Open championship weekend. This hotel is an official Cincinnati open hotel where many players were staying. Very well maintained but looked a little quiet. The occupancy might be very low. The restaurants in the property were closed for special events mostly probably for the Cincinnati Open. Overall good hotel.

Reviewed on Aug. 18, 2025

Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Price was CA $2,204, price is now CA $1,700 per person
CA $1,700
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9.6/10 Exceptional! (1,007 reviews)
Lovely space with friendly service and great vibe - always a fav when we are passing through!

Reviewed on Aug. 17, 2025

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Bennington Hotel Deals

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
777 Belterra Drive, Florence, IN
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Sep 1 to Sep 2
CA $165
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"Beautiful resort. Lobby and restaurants were conveniently located and the staff were friendly and welcoming. The rooms were spacious and comfortable."

Reviewed on Aug. 22, 2025

Belterra Casino Resort
Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

2.5 out of 5
525 Dale Drive I 71 Exit 57 Sp, Sparta, KY
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Aug 31 to Sep 1
CA $100
CA $110 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Great breakfast"

Reviewed on Aug. 19, 2025

Ramada by Wyndham Sparta/At Speedway
Rising Star Casino Resort

Rising Star Casino Resort

2 out of 5
777 Rising Star Drive, Rising Sun, IN
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Aug 27 to Aug 28
CA $137
CA $171 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (579 reviews)
"Beautiful hotel and clean"

Reviewed on Jul. 30, 2025

Rising Star Casino Resort
See all 144 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 can snap up a vacation package to this popular destination from CA $895 on Expedia. However, how much your vacation to Bennington costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Bennington?
January, February and November are the best times to look for cheap Bennington vacation packages. Choosing to travel in less busy periods means you can generally find lower prices on hotels and flights.
How many days is enough for Bennington?
The ideal length for your Bennington vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to go to all the major attractions and discover some hidden treasures along the way.
How to find the best Bennington package deals?
Use Expedia's filter tool to 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're looking to save, plan your trip for midweek, or search for Bennington package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Bennington vacation as a package?
You can enjoy significant savings on your Bennington break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Bennington?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Bennington break.
How to plan a trip to Bennington?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Bennington.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and flights. Your accommodations will probably be the biggest expense during your trip to Bennington.
  3. Decide how long to go for: Now that you're up to speed on Bennington, you can figure out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Bennington vacation package.

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