Jamestown Vacation Rentals

Compare 5 vacation rentals.
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Make Jamestown your next getaway

Jamestown, KY vacation rentals

Top Jamestown property types

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House rentals

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Popular amenities for Jamestown vacation rentals

Popular
Dog-friendly Internet Lake view
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
4 Bedroom | 3 Bath | Sleeps 20

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre! - Jamestown, KY

$415 avg / night
(excludes fees and taxes)
4.89 (9)
Lake Cumberland Retreat w/ Deck & Views!
6 Bedroom | 5 Bath | Sleeps 15

Lake Cumberland Retreat w/ Deck & Views! - Jamestown, KY

$476 avg / night
(excludes fees and taxes)
5.0 (1)
Fun w/ Family! Lakefront Gem in Jamestown w/ Dock
3 Bedroom | 2.5 Bath | Sleeps 10

Fun w/ Family! Lakefront Gem in Jamestown w/ Dock - Jamestown, KY

$350 avg / night
(excludes fees and taxes)
2 Mi to Lake Cumberland: Family-Friendly Retreat!
3 Bedroom | 2 Bath | Sleeps 10

2 Mi to Lake Cumberland: Family-Friendly Retreat! - Jamestown, KY

$174 avg / night
(excludes fees and taxes)
2 Mi to Lake Cumberland Access: Home w/ Grill
4 Bedroom | 2 Bath | Sleeps 11

2 Mi to Lake Cumberland Access: Home w/ Grill - Jamestown, KY

$196 avg / night
(excludes fees and taxes)

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Browse more vacation rental amenities in Jamestown

Water view | Waterfront | A/C | Washer/dryer | Balcony | Bikes | Pool table | Kayaks | Snowbird-friendly

Recent Jamestown guest reviews

From the moment we arrived, this property felt like a dream come true. The panoramic lake views from the deck were absolutely breathtaking—morning coffee never tasted so good. Inside, every detail was perfect: the layout made it feel spacious yet cozy, everything was spotless, and the thoughtful organization made settling in effortless. You can tell the owners truly care about creating a special experience. This is, without a doubt, one of the finest places to stay in the Lake Cumberland area. If I could give it more than five stars, I would in a heartbeat. I’m already looking forward to coming back and making more memories here!
Zachary . | Aug 2025
Great place to hang out with family.
Brian . | Jan 2025
2nd time we Have Been there. And will definitely be back Private and quiet and awesome view at the back of the property.
Eddie . | Nov 2024
Jamestown vacation rental FAQ

Yes. 11 of our Jamestown vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Jamestown vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Jamestown team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Jamestown, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

Appalachian Mountains   |   Russell Springs   |   Faubush   |   Seventy Six   |   Columbia   |   Monticello   |   Nancy   |   Albany   |   Burkesville   |   Bronston   |   Burnside   |   Somerset   |   Byrdstown   |   Kentucky
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