Jeffersonville - Clarksville Vacations from $592

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The Latest Jeffersonville - Clarksville vacation packages

Price found within the past 48 hours. Click for updated prices.
Regina's Country Livin'

Regina's Country Livin'

$592
per person
Oct 19 - Oct 24
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
10/10 Exceptional! (10 reviews)
For my first time visiting in Kentucky, I’m glad I picked to stay at Regina’s Country Living. Hostess : Top notch hospitality; Regina looked out for everyone who stayed for the Kentucky Derby event like a mother. Our breakfast was homemade each morning, and it definitely brought back memories with of my grandma for Sunday and Christmas breakfast specials. Room/Home : Regina’s home had so much old southern world charm that had it not been so cool outside, that drinking a Mint Julep on the porch would have been a pleasant experience. I stayed in the “ King’s Room “, my bed was huge and the covers were soft and inviting. I slept good everyday I was there and I slept really good after the Derby. Each room had a story to tell and I’d especially liked the sky light in the family room. The park adjacent to the house is such a nice addition for anyone who just wants to take a walk or run. It’s perfect if you bring a dog with you on your stay as well. Thank you, Regina for opening up your home and being an amazing woman. Thank you for sharing an amazing friendly dinner with me at the Mexican restaurant and making sure a solo traveler felt like family even if it was for a few days. Looking forward to next year’s Kentucky Derby at your Bed and Breakfast.

Reviewed on May 4, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

Downtown Louisville
Save 100% on your flight
$1,257
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!

Reviewed on Aug 16, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

Shively
$1,406
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,013 reviews)
Our stay was fine. Was not aware of the extra $150 hold. Also it does not seem to be located in the best of areas. I have no real complaints but I will not return.

Reviewed on Aug 24, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

Downtown Louisville
$1,337
per person
Oct 26 - Nov 1
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (491 reviews)
The staff were very helpf and the room was clean. We had dinner at Repeal, our server was Justin. He is the sommelier - amazing tips for our weekend bourbon hunting trail.

Reviewed on Aug 23, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

Downtown Louisville
$1,011
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.2/10 Wonderful! (815 reviews)
Loved Moxy. Staff was outstanding. Perfect location. Very quiet for downtown Louisville.

Reviewed on Aug 23, 2026

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Stay near popular Jeffersonville - Clarksville attractions

A river with rocks and a bridge in the background.
Photo by Eric O

Falls of the Ohio State Park

8.4/10 (61 reviews)
You can take time to visit Falls of the Ohio State Park during your travels to Clarksville. Stroll along the area's riverfront or experience its acclaimed theater scene.
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A colorful playground with a large red slide, a water fountain, and a decorative archway.

Atlantis Waterpark

7.6/10 (37 reviews)
Bring the kiddos to Atlantis Waterpark and enjoy some excitement at this theme park in Clarksville. Stroll along the riverfront or attend a sporting event in the area.
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Derby Dinner Playhouse

8.4/10 (58 reviews)
You can make plans for a show at Derby Dinner Playhouse on your trip to Clarksville. Amble around the area's riverfront or attend a sporting event.
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Covered Bridge Golf Club

7.0/10 (6 reviews)
Enjoy a round of golf in Sellersburg at Covered Bridge Golf Club. Stroll along the area's riverfront, or simply savor its top-notch restaurants.
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Turtle Run Winery

8.8/10 (11 reviews)
You can enjoy a tasting or tour at Turtle Run Winery during your travels to Corydon. While you're in the area, find time to visit its casinos.
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Corydon Capitol State Historic Site

9.0/10 (20 reviews)
You can spend time exploring the galleries in Corydon Capitol State Historic Site during your travels in Corydon. While you're in the area, find time to visit its casinos.
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Indiana University Southeast

Explore the campus of Indiana University Southeast as part of your travels around New Albany. Wander the riverfront in this family-friendly area.
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Harrison Spring

Explore the great outdoors at Harrison Spring, a lovely green space in Corydon. While in this family-friendly area, you can enjoy the restaurants.
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Jeffersonville - Clarksville Hotel Deals

Radisson Hotel Louisville North

Radisson Hotel Louisville North

505 Marriott Drive Clarksville IN
Fully refundableReserve now, pay when you stay
$60 nightly
$68 total
Aug 31 - Sep 1
Total with taxes and fees
7/10 Good! (3,348 reviews)
"My family and I were looking forward to staying at this hotel for our weekend trip based on the reviews we had read concerning how clean previous visitors were saying it was and nice it was. I'm not sure what folks standards are for cleanliness, but it's definitely far off! I can understand the hotel ..."

Reviewed on Aug 23, 2026

Radisson Hotel Louisville North
Derby Hotel & Suites

Derby Hotel & Suites

505 K Marriot Dr Clarksville IN
Fully refundableReserve now, pay when you stay
$55 nightly
$62 total
Aug 31 - Sep 1
Total with taxes and fees
6.8/10 (179 reviews)
"The room was ok nothing like the website portrayed. The staff was friendly. I had to pay a $50 deposit incase any damages were done to the room which I've never had to do. I better not see that charge on my card. I won't be returning."

Reviewed on Aug 23, 2026

Derby Hotel & Suites
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination

Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination

11999 Casino Center Drive SE Elizabeth IN
$84 nightly
$93 total
Sep 23 - Sep 24
Total with taxes and fees
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination
See all 2,381 properties in Jeffersonville - Clarksville
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.

Find the Best Jeffersonville - Clarksville Vacation Packages

Jeffersonville - Clarksville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Louisville Intl. Airport (SDF)
Population
21,900

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