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 NZ$637 per night from 7 Jan to 8 Jan
NZ$637
includes taxes & fees
7 Jan - 8 Jan 2025
Book a stay at this family-friendly vacation home in Monticello. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions ...
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, private pools, and a garden. Popular attractions Burnside Marina and Zollicoffer ...
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
Stay at this vacation home in Nancy. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Lake Cumberland Winery and Zollicoffer Park are ...
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
Stay at this vacation home in Nancy. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attraction Lake Cumberland Winery is located ...
"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
Stay at this vacation home in Jamestown. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attraction 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
Stay at this vacation home in Columbia. Enjoy free WiFi, a garden, and patios. Popular attractions Casey Creek and Green River Lake are located nearby.
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy patios, cable/satellite TV service, and in-room washers/dryers. Popular attraction Lake ...
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
Stay at this vacation home in Byrdstown. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions 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 NZ$735 per night from 24 Dec to 25 Dec
NZ$735
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this family-friendly vacation home in Jamestown. Enjoy free WiFi, a garden, and patios. Popular attraction Lake Cumberland State Resort Park is ...
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
168 Holiday Homes
Lowest Price
NZ$157
Highest Price
NZ$735
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 NZ$157 per night from 3 Jan to 4 Jan
NZ$157
includes taxes & fees
3 Jan - 4 Jan 2025
Stay at this 3-star family-friendly holiday park in Jamestown. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. ...
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
Stay at this cottage in Jamestown. Enjoy an in-room coffeemaker and air conditioning. Popular attraction Lake Cumberland State Resort Park is located ...
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
Book a stay at this family-friendly vacation home in Jamestown. Enjoy a garden, furnished patios, and in-room washers/dryers. Popular attraction Lake Cumberland ...
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
Stay at this cabin in Jamestown. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attraction Lake Cumberland State Resort Park is ...
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.