Bennington Vacations from $359

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The Latest Bennington vacation packages

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 $586, price is now $359 per person
$359
per person
Nov 20 - Nov 24
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $598, price is now $398 per person
$398
per person
Nov 20 - Nov 24
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (771 reviews)
I really liked our stay there. The rooms were very nice and clean. The front desk staff was wonderful and went above and beyond. The waitstaff in the restaurant and pool areas were also wonderful and extremely helpful. The morning bar staff was excellent as well. The night staff at the bar however were less than accommodating. I sat at the bar and had to wait 10 minutes before being waited on while the staff talked to each other. I then asked to cash out for my one drink and had to wait for 15 to 20 minutes, and the blonde girl that had been waiting on me was eating food instead of just cashing me out. We thoroughly enjoyed our overall experience. We just had that one bad experience but thought you should know that it wasn't great customer service.

Reviewed on Aug 29, 2025

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was $618, price is now $429 per person
$429
per person
Nov 20 - Nov 24
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (3,553 reviews)
The hotel was great! Everything we thought it would be

Reviewed on Aug 31, 2025

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

3 out of 5
Save 100% on your flight
Price was $1,004, price is now $734 per person
$734
per person
Nov 20 - Nov 24
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
No reviews
Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

4 out of 5
Downtown Louisville
Price was $580, price is now $425 per person
$425
per person
Nov 20 - Nov 24
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (1,007 reviews)
Friendly staff. Comfortable room. My bathroom was a little dirty but nothing that a Clorox wipe couldn’t fix!

Reviewed on Aug 29, 2025

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Discover the most popular places to visit in Bennington

The Ridge Winery Tasting Room

4.5/5(2 reviews)

You can enjoy a tasting or tour at The Ridge Winery Tasting Room during your travels to Vevay. Check out the casinos and top-notch restaurants in this relaxing area.

The Ridge Winery Tasting Room

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
$155 nightly
The price is $173 total per night from Sep 1 to Sep 2
$173 total
Sep 1 - Sep 2
Total with taxes and 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
$72 nightly
The price is $79 total per night from Sep 7 to Sep 8
$79 total
Sep 7 - Sep 8
Total with taxes and fees
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
$110 nightly
The price is $124 total per night from Sep 1 to Sep 2
$124 total
Sep 1 - Sep 2
Total with taxes and fees
Rising Star Casino Resort
See all 146 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?
Offering excellent value package deals from $359 on Expedia, you'll be thrilled with how little a vacation to Bennington costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Bennington?
If you're hoping to book a cheap Bennington vacation package, consider visiting in November, December and January. You'll typically find better rates on hotels and airfares during these months — ideal for travelers wishing to save money.
How many days is enough for Bennington?
With a well-organized itinerary, you can easily visit the main Bennington sights in a handful of days. But if you want to discover hidden spots or go on day tours, consider booking your Bennington vacation for longer.
How to find the best Bennington package deals?
Begin your search for a Bennington package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Bennington package deal right away, just play around with your dates and search again. Bear 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?
An Expedia vacation package could score you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Bennington getaway to match your exact needs. 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 planning a spontaneous Bennington getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Bennington vacation packages?
Your Bennington break is meant to be a relaxing escape from your daily routine, not a source of money worries. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.