Cheap Vacations in Lake Cumberland

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Flight deals to Lake Cumberland

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

Mon, Dec 29 - Fri, Jan 9
IAH
Houston
LEX
Lexington
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Dec 29 from Houston to Lexington, returning Fri, Jan 9, priced at $251 found 3 days ago
Thu, Jan 8 - Sun, Jan 11
SAN
San Diego
LEX
Lexington
$286 Roundtrip, found 1 day ago
$286
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Jan 8 from San Diego to Lexington, returning Sun, Jan 11, priced at $286 found 1 day ago
Thu, Feb 26 - Sun, Mar 1
LAX
Los Angeles
LEX
Lexington
$289 Roundtrip, found 4 days ago
$289
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Feb 26 from Los Angeles to Lexington, returning Sun, Mar 1, priced at $289 found 4 days ago

Top rated hotels for your Lake Cumberland vacation

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

3 out of 5
5465 State Park Rd Jamestown KY
2.93 mi from city center
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When you stay at Lake Cumberland State Resort Park in Jamestown, you'll be 6 minutes by car from Lowgap Island.
Pool
Pet friendly
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Jamestown KY
5.53 mi from city center
$558 nightly
The price is $615 total per night
$615 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
When you stay at this vacation home in Jamestown, you'll be on the waterfront, within a 5-minute drive of The Park at Jamestown Square and Judicial Center Fountain Park.
Kitchen
Washer
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

Monticello KY
20.49 mi from city center
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Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.
Pool
Hot Tub
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.