Book Holiday Homes in Jamestown

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Featured Holiday Homes in Jamestown

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Monticello
The price is AU$583 per night from 7 Jan to 8 Jan
AU$583
includes taxes & fees
7 Jan - 8 Jan 2025
When you stay at this vacation home in Monticello, you'll be on a lake and within a 5-minute drive of Cumberland River.
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

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

Monticello
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Marina.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Little blue house on the lake

Little blue house on the lake

Nancy
When you stay at this vacation home in Nancy, you'll be on a lake and 9 minutes by foot from Cumberland River.
Little blue house on the lake
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"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

Nancy
With a stay at this vacation home in Nancy, you'll be on a lake, and 16.1 mi (26 km) from Mill Springs National Battlefield Visitor Center and 16.8 mi (27 km) ...
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Jamestown
With a stay at this vacation home in Jamestown, you'll be 8.5 mi (13.6 km) from Lake Cumberland State Resort Park and 12 mi (19.3 km) from Wolf Creek National ...
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
Lake House near Green River Lake and minutes from several marinas.

Lake House near Green River Lake and minutes from several marinas.

Columbia
Located in Columbia, this vacation home is on a lake, within a 15-minute drive of Green River Lake and Casey Creek.
Lake House near Green River Lake and minutes from several marinas.
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina

Lake Cumberland Home 1/2 Mi to Beaver Creek Marina

Monticello
When you stay at this vacation home in Monticello, you'll be 14 minutes by car from Cumberland River.
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina
Dale Hollow Lake getaway tucked in the woods, one minute from the lake!

Dale Hollow Lake getaway tucked in the woods, one minute from the lake!

Byrdstown
Located in Byrdstown, this vacation home is within a 15-minute drive of Eagle Cove Marina and Star Point Marina.
Dale Hollow Lake getaway tucked in the woods, one minute from the lake!
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Jamestown
The price is AU$672 per night from 5 Jan to 6 Jan
AU$672
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at this vacation home in Jamestown, you'll be 5 minutes by car from Cumberland River.
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
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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.

Jamestown Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Jamestown vacation homes are the perfect way for you to wing it.

Holiday houses in Jamestown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Jamestown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Jamestown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Jamestown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Jamestown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Jamestown Holiday Homes essential information

Accommodation
169 Holiday Homes
Lowest Price
AU$142
Highest Price
AU$672
Popular accommodation
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!, 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍 , Little blue house on the lake, "Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake, Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community, Lake House near Green River Lake and minutes from several marinas., Lake Cumberland Home 1/2 Mi to Beaver Creek Marina, Dale Hollow Lake getaway tucked in the woods, one minute from the lake!, Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Top trending hotels in Jamestown

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

3 out of 5
5465 State Park Rd, Jamestown, KY
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 3 Jan to 4 Jan
AU$142
includes taxes & fees
3 Jan - 4 Jan 2025
With a stay at Lake Cumberland State Resort Park in Jamestown, you'll be 5.6 mi (9 km) from Lake Cumberland State Resort Park and 9.4 mi (15.2 km) from Wolf ...
Lake Cumberland State Resort Park
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Jamestown
When you stay at this cottage in Jamestown, you'll be on a lake and 7 minutes by foot from Cumberland River.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Jamestown
When you stay at this vacation home in Jamestown, you'll be on the waterfront and 14 minutes by car from Cumberland River.
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
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Secluded Jamestown Cabin w/ Fire Pit!

Secluded Jamestown Cabin w/ Fire Pit!

Jamestown
When you stay at this cabin in Jamestown, you'll be 4 minutes by foot from Cumberland River.
Secluded Jamestown Cabin w/ Fire Pit!
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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.

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^Subject to availability and chosen travel dates.