Bennington Vacation Packages

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

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Top Bennington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hillcrest Motel By OYO Aurora IN Near Lawrenceburg

Hillcrest Motel By OYO Aurora IN Near Lawrenceburg

2.5 out of 5
Price was CA $1,180, price is now CA $955 per person
CA $955
per person
Sep 10 - Sep 17
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
6.6/10 (63 reviews)

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was CA $1,776, price is now CA $1,300 per person
CA $1,300
per person
Sep 10 - Sep 17
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
8.6/10 Excellent! (1,000 reviews)

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,970, price is now CA $1,630 per person
CA $1,630
per person
Oct 8 - Oct 12
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
9.6/10 Exceptional! (483 reviews)
The staff was their best asset! Very helpful, friendly, tried to accommodate any need!! Rooms were clean and beds were comfy!! We ate at the steakhouse in the hotel. Great food and our waitress was absolutely the best!!! The lobby could accommodate several groups of people!! Would stay there again!!

Reviewed on Jul 13, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was CA $1,769, price is now CA $1,483 per person
CA $1,483
per person
Oct 13 - Oct 16
found 2 hours ago
Roundtrip flight included
Philadelphia (PHL) to Louisville (SDF)
9/10 Wonderful! (1,004 reviews)

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,541, price is now CA $1,340 per person
CA $1,340
per person
Oct 13 - Oct 16
found 2 hours ago
Roundtrip flight included
Philadelphia (PHL) to Louisville (SDF)
8.8/10 Excellent! (1,009 reviews)
Resort staff was very friendly and accommodating to our early arrival. Facilities are very well, upkeep, respectful staff, in walking distance of the downtown attractions and restaurants as well as the YUM Center.

Reviewed on Jul 20, 2026

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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 $178 per night from Jul 26 to Jul 27
CA $178
CA $216 total
Jul 26 - Jul 27
includes taxes & fees
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 $89 per night from Aug 16 to Aug 17
CA $89
CA $99 total
Aug 16 - Aug 17
includes taxes & fees
Ramada by Wyndham Sparta/At Speedway
Best Way Inn Madison

Best Way Inn Madison

2.5 out of 5
700 Clifty Drive Madison IN
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Jul 21 to Jul 22
CA $111
CA $127 total
Jul 21 - Jul 22
includes taxes & fees
7/10 Good! (552 reviews)
"This was one of the few rooms left in town for Madison Regatta 2026. Pretty standard for a pet friendly hotel, we were traveling without our dog, definitely in need of a massive remodel. Front desk had a left over Covid glass in place, so communication required asking for repeats at loud volumes ..."

Reviewed on Jul 7, 2026

Best Way Inn Madison
See all 172 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 $955 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.