
Cumberland Cultural Heritage Highway Vacations from $400
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The Latest Cumberland Cultural Heritage Highway vacation packages
Price found within the past 48 hours. Click for updated prices.


The Grady
Downtown Louisville
Price was $824, price is now $639 per person
$639
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.4/10 Exceptional! (1,000 reviews)
Always one my favorite places to stay!! However, Mark downstairs made some long mornings quite pleasurable with his attentive service and friendly tableside manner. Told us a lot of cool things about the history of the area and hotel. Shout out to Chef for the great breakfasts as well!!
Reviewed on Aug 26, 2025

The Brown Hotel
Downtown Louisville
Price was $635, price is now $508 per person
$508
per person
Oct 24 - Oct 27
just found
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9.4/10 Exceptional! (1,053 reviews)
The hotel is beautiful and the staff were all so friendly and helpful. We had dinner at the restaurant and the food was definitely some of the best we've had! And our waiter Chris was attentive and had a great sense of humor and made our night very enjoyable. The room was clean and spacious only complaint I have is the bed was not very comfortable and not memory foam but a traditional mattress where you could feel every single movement during the night which is a downside for us because my hubby and I toss and turn a lot and we are used to a softer memory foam bed. Amy at check in was delightful and helpful and so was the lady at check out but I didn't catch her name. So other than the mattress our stay was wonderful and I'd definitely stay here again especially if they upgrade the mattresses.
Reviewed on Aug 24, 2025


Embassy Suites Louisville East
Price was $523, price is now $440 per person
$440
per person
Oct 24 - Oct 27
just found
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
It was extremely clean. It was in a very quiet area. I have always enjoyed my stays at embassy suites hotels
Reviewed on Jul 27, 2025
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Red Roof Inn Somerset, KY
1201 S Highway 27, Somerset, KY
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Aug 31 to Sep 1
$72 total
Aug 31 - Sep 1
Total with taxes and fees

Lake Cumberland State Resort Park
5465 State Park Rd, Jamestown, KY
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $116 total per night from Sep 8 to Sep 9
$116 total
Sep 8 - Sep 9
Total with taxes and fees

Holiday Inn Express & Suites Glasgow by IHG
208 Wall Street, Glasgow, KY
$130 nightly
The price is $143 total per night from Sep 28 to Sep 29
$143 total
Sep 28 - Sep 29
Total with taxes and fees
9/10 Wonderful! (725 reviews)
"Very close to everything quite at night. Breakfast was great!! Would stay here again."
Reviewed on Aug 24, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.