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Monticello Vacation Packages

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Monticello Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

2.5 out of 5
Price was $661, price is now $557 per person
$557
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Louisville Slugger Museum and KFC Yum Center are located nearby.
Nice stay

Reviewed on Aug 24, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Save 100% on your flight
Price was $1,696, price is now $1,235 per person
$1,235
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip 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 KFC Yum Center and Louisville Slugger Museum are located nearby.
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

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Price was $1,726, price is now $1,337 per person
$1,337
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions KFC Yum Center and Louisville Slugger Museum are located nearby.

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Price was $1,734, price is now $1,368 per person
$1,368
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip 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 Churchill Downs and L&N Federal Credit Union Stadium are located nearby.
Clean room and helpful staff. Breakfast options were not enough.

Reviewed on Aug 24, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Price was $1,267, price is now $1,011 per person
$1,011
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this family-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Louisville Slugger Museum are located nearby.
Loved Moxy. Staff was outstanding. Perfect location. Very quiet for downtown Louisville.

Reviewed on Aug 23, 2026

The Reserve on Main

The Reserve on Main

4 out of 5
Save 100% on your flight
Price was $3,704, price is now $2,997 per person
$2,997
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Stay at this aparthotel in Louisville. Enjoy free WiFi, onsite spa services, and cable TV channels. Popular attractions Louisville Slugger Museum and KFC Yum Center are located nearby.

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Price was $666, price is now $558 per person
$558
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip 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 L&N Federal Credit Union Stadium are located nearby.
The staff was extremely nice and helpful starting the min we checked in

Reviewed on Aug 24, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Price was $1,199, price is now $1,007 per person
$1,007
per person
Sep 30 - Oct 4
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Louisville Slugger Museum are located nearby.

Monticello Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination

Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $734, price is now $547 per person
$547
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Louisville (SDF)
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $771, price is now $595 per person
$595
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $1,090, price is now $877 per person
$877
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Louisville (SDF)
The Reserve on Main

The Reserve on Main

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $3,704, price is now $2,997 per person
$2,997
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)

Monticello Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination

Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $880, price is now $665 per person
$665
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Louisville (SDF)
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $1,696, price is now $1,235 per person
$1,235
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $1,726, price is now $1,337 per person
$1,337
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was $1,045, price is now $813 per person
$813
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)

Top Flight Deals

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

Breeze Airways
Thu, Nov 12 - Sun, Nov 15
TPA
Tampa Intl.
SDF
Louisville Intl.
$142 Roundtrip, found 15 hours ago
$142
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Tampa Intl. to Louisville Intl., returning Sun, Nov 15, priced at $142 found 15 hours ago
Delta
Fri, Sep 18 - Sat, Sep 19
DEN
Denver Intl.
SDF
Louisville Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 18 from Denver Intl. to Louisville Intl., returning Sat, Sep 19, priced at $237 found 2 days ago
Delta
Tue, Sep 22 - Sat, Oct 3
DFW
Dallas-Fort Worth Intl.
SDF
Louisville Intl.
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 22 from Dallas-Fort Worth Intl. to Louisville Intl., returning Sat, Oct 3, priced at $240 found 4 days ago
Bargain Flight
Tue, Oct 6 - Tue, Oct 13
MSP
Minneapolis - St. Paul Intl.
SDF
Louisville Intl.
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Oct 6 from Minneapolis - St. Paul Intl. to Louisville Intl., returning Tue, Oct 13, priced at $241 found 1 day ago