Search Deals on
Pleasureville Vacation Packages

Build your package with 2 more options

Pleasureville Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Price was $466, price is now $377 per person
$377
per person
Aug 27 - Aug 31
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
Book a stay at this luxury hotel in Cincinnati. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Paycor Stadium and Great American Ball Park are located nearby.

Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Save 100% on your flight
Price was $739, price is now $571 per person
$571
per person
Aug 27 - Aug 31
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
Book a stay at this business-friendly hotel in Covington. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Paycor Stadium and Great American Ball Park are located nearby.

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Price was $730, price is now $569 per person
$569
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kentucky Kingdom and Churchill Downs are located nearby.

The Purple Martin

The Purple Martin

2 out of 5
Price was $1,642, price is now $1,309 per person
$1,309
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this golf hotel in Prospect. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Chamberlain Pointe Shopping Center and Old Brownsboro Crossing Shopping Center are located nearby.
Amazing property… I would come back in a heartbeat!

Reviewed on Jun 19, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Price was $815, price is now $651 per person
$651
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Kingdom and Fourth Street Live! are located nearby.

Beaumont Inn

Beaumont Inn

2 out of 5
Price was $775, price is now $622 per person
$622
per person
Oct 13 - Oct 19
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Stay at this hotel in Harrodsburg. Enjoy free WiFi, an outdoor pool, and a 24-hour front desk. Popular attractions Young Park and Fort Harrod State Park are located nearby.

Clarion Pointe Harrodsburg-Danville

Clarion Pointe Harrodsburg-Danville

2.5 out of 5
Price was $696, price is now $561 per person
$561
per person
Oct 13 - Oct 19
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Book a stay at this business-friendly hotel in Harrodsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions The Big Stream Park and Fort Harrod State Park are located nearby.
The room was very clean and wasn't bothered by anything verry nice stay quiet. The staff got me checked in and out quickly.

Reviewed on Jul 17, 2026

Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North

2.5 out of 5
Price was $718, price is now $584 per person
$584
per person
Oct 13 - Oct 19
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Book a stay at this business-friendly hotel in Georgetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Horse Park and The Pavillion are located nearby.
Clean and friendly staff.

Reviewed on Jul 21, 2026

Pleasureville Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $730, price is now $569 per person
$569
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Central Business District
Save 100% on your flight
Price was $739, price is now $571 per person
$571
per person
Aug 27 - Aug 31
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
The Purple Martin

The Purple Martin

2 out of 5
Price was $1,642, price is now $1,309 per person
$1,309
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $815, price is now $651 per person
$651
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)

Pleasureville Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Harrodsburg-Danville

Clarion Pointe Harrodsburg-Danville

2.5 out of 5
Price was $696, price is now $561 per person
$561
per person
Oct 13 - Oct 19
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $1,170, price is now $936 per person
$936
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Beaumont Inn

Beaumont Inn

2 out of 5
Price was $775, price is now $622 per person
$622
per person
Oct 13 - Oct 19
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North

2.5 out of 5
Price was $718, price is now $584 per person
$584
per person
Oct 13 - Oct 19
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Tue, Sep 22 - Wed, Oct 7
JFK
John F. Kennedy Intl.
LEX
Blue Grass
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 22 from John F. Kennedy Intl. to Blue Grass, returning Wed, Oct 7, priced at $281 found 1 day ago
Bargain Flight
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
LEX
Blue Grass
$285 Roundtrip, found 4 days ago
$285
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Sep 29 from Los Angeles Intl. to Blue Grass, returning Sat, Oct 3, priced at $285 found 4 days ago
Bargain Flight
Tue, Sep 22 - Tue, Oct 6
SEA
Seattle - Tacoma Intl.
LEX
Blue Grass
$291 Roundtrip, found 4 days ago
$291
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Sep 22 from Seattle - Tacoma Intl. to Blue Grass, returning Tue, Oct 6, priced at $291 found 4 days ago
Delta
Mon, Oct 12 - Mon, Oct 19
IAH
George Bush Intercontinental
LEX
Blue Grass
$319 Roundtrip, found 22 hours ago
$319
Roundtrip
found 22 hours ago
Select Delta flight, departing Mon, Oct 12 from George Bush Intercontinental to Blue Grass, returning Mon, Oct 19, priced at $319 found 22 hours ago