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Holiday Rentals in Jamestown

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Bedrooms

Bathrooms

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5 km
58 rentals in Jamestown.
LAKE CUMBERLAND: Above JAMESTOWN MARINA�Laking, Hiking, Relaxing. Pet Friendly., holiday rental in Jamestown
LAKE CUMBERLAND: Above JAMESTOWN MARINA�Laking, Hiking, Relaxing. Pet Friendly., holiday rental in Jamestown
LAKE CUMBERLAND: Above JAMESTOWN MARINA�Laking, Hiking, Relaxing. Pet Friendly., holiday rental in Jamestown

LAKE CUMBERLAND: Above JAMESTOWN MARINA�Laking, Hiking, Relaxing. Pet Friendly.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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LAKE CUMBERLAND: AMAZING☀️Year-Round Lake Views. Minutes from JAMESTOWN MARINA, holiday rental in Jamestown
LAKE CUMBERLAND: AMAZING☀️Year-Round Lake Views. Minutes from JAMESTOWN MARINA, holiday rental in Jamestown
LAKE CUMBERLAND: AMAZING☀️Year-Round Lake Views. Minutes from JAMESTOWN MARINA, holiday rental in Jamestown

LAKE CUMBERLAND: AMAZING☀️Year-Round Lake Views. Minutes from JAMESTOWN MARINA

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Studio apartment with bunkroom just 3 miles from Jamestown Marina!, holiday rental in Jamestown
Studio apartment with bunkroom just 3 miles from Jamestown Marina!, holiday rental in Jamestown
Studio apartment with bunkroom just 3 miles from Jamestown Marina!, holiday rental in Jamestown

Studio apartment with bunkroom just 3 miles from Jamestown Marina!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Unit B - 2 queen beds, 1 full bath, queen sleeper sofa, close to lake, holiday rental in Jamestown
Unit B - 2 queen beds, 1 full bath, queen sleeper sofa, close to lake, holiday rental in Jamestown
Unit B - 2 queen beds, 1 full bath, queen sleeper sofa, close to lake, holiday rental in Jamestown

Unit B - 2 queen beds, 1 full bath, queen sleeper sofa, close to lake

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lake House Hideaway #2-Only 1 Mile from Jamestown Marina!, holiday rental in Jamestown
Lake House Hideaway #2-Only 1 Mile from Jamestown Marina!, holiday rental in Jamestown
Lake House Hideaway #2-Only 1 Mile from Jamestown Marina!, holiday rental in Jamestown

Lake House Hideaway #2-Only 1 Mile from Jamestown Marina!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community, holiday rental in Jamestown
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community, holiday rental in Jamestown
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community, holiday rental in Jamestown

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lake Cumberland custom log cabin home on 32 wooded acres, holiday rental in Jamestown
Lake Cumberland custom log cabin home on 32 wooded acres, holiday rental in Jamestown
Lake Cumberland custom log cabin home on 32 wooded acres, holiday rental in Jamestown

Lake Cumberland custom log cabin home on 32 wooded acres

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Ultimate Getaway on Lake Cumberland, Great Location and Rare Private Dock & Ramp, holiday rental in Jamestown
Ultimate Getaway on Lake Cumberland, Great Location and Rare Private Dock & Ramp, holiday rental in Jamestown
Ultimate Getaway on Lake Cumberland, Great Location and Rare Private Dock & Ramp, holiday rental in Jamestown

Ultimate Getaway on Lake Cumberland, Great Location and Rare Private Dock & Ramp

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat., holiday rental in Jamestown
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat., holiday rental in Jamestown
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat., holiday rental in Jamestown

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Lake House Hideaway #1, Only 2 miles from Jamestown Marina!!, holiday rental in Jamestown
Lake House Hideaway #1, Only 2 miles from Jamestown Marina!!, holiday rental in Jamestown
Lake House Hideaway #1, Only 2 miles from Jamestown Marina!!, holiday rental in Jamestown

Lake House Hideaway #1, Only 2 miles from Jamestown Marina!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 Bdrm Lake House Getaway - Three Minutes To Launch!, holiday rental in Jamestown
3 Bdrm Lake House Getaway - Three Minutes To Launch!, holiday rental in Jamestown
3 Bdrm Lake House Getaway - Three Minutes To Launch!, holiday rental in Jamestown

3 Bdrm Lake House Getaway - Three Minutes To Launch!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic Union Chapel Elementary School near Cumberland River & Lake, holiday rental in Jamestown
Historic Union Chapel Elementary School near Cumberland River & Lake, holiday rental in Jamestown
Historic Union Chapel Elementary School near Cumberland River & Lake, holiday rental in Jamestown

Historic Union Chapel Elementary School near Cumberland River & Lake

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Lake Cumberland Cabin Hideaway-Only 2 miles from Jamestown Marina, holiday rental in Jamestown
Lake Cumberland Cabin Hideaway-Only 2 miles from Jamestown Marina, holiday rental in Jamestown
Lake Cumberland Cabin Hideaway-Only 2 miles from Jamestown Marina, holiday rental in Jamestown

Lake Cumberland Cabin Hideaway-Only 2 miles from Jamestown Marina

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Family Lake House nestled in the woods of Lake Cumberland!, holiday rental in Jamestown
Family Lake House nestled in the woods of Lake Cumberland!, holiday rental in Jamestown
Family Lake House nestled in the woods of Lake Cumberland!, holiday rental in Jamestown

Family Lake House nestled in the woods of Lake Cumberland!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 18
Match: Sleeps
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Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland, holiday rental in Jamestown
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland, holiday rental in Jamestown
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland, holiday rental in Jamestown

Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cumberland Get-A-Way located at entrance of State Park, holiday rental in Jamestown
Cumberland Get-A-Way located at entrance of State Park, holiday rental in Jamestown
Cumberland Get-A-Way located at entrance of State Park, holiday rental in Jamestown

Cumberland Get-A-Way located at entrance of State Park

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 28
Match: Sleeps
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Lake house. Less than 3 miles from beautiful Lake Cumberland., holiday rental in Jamestown
Lake house. Less than 3 miles from beautiful Lake Cumberland., holiday rental in Jamestown
Lake house. Less than 3 miles from beautiful Lake Cumberland., holiday rental in Jamestown

Lake house. Less than 3 miles from beautiful Lake Cumberland.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!, holiday rental in Jamestown
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!, holiday rental in Jamestown
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!, holiday rental in Jamestown

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Lake Cumberland Jamestown New Home near State Park & Boat Ramps, holiday rental in Jamestown
Lake Cumberland Jamestown New Home near State Park & Boat Ramps, holiday rental in Jamestown
Lake Cumberland Jamestown New Home near State Park & Boat Ramps, holiday rental in Jamestown

Lake Cumberland Jamestown New Home near State Park & Boat Ramps

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Hodgepodge Lodge, holiday rental in Jamestown
The Hodgepodge Lodge, holiday rental in Jamestown
The Hodgepodge Lodge, holiday rental in Jamestown

The Hodgepodge Lodge

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Camper on campsite, holiday rental in Jamestown
Camper on campsite, holiday rental in Jamestown
Camper on campsite, holiday rental in Jamestown

Camper on campsite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Unit A  - 2 queen beds, 1 full bath, sleeper sofa, close to lake, holiday rental in Jamestown
Unit A  - 2 queen beds, 1 full bath, sleeper sofa, close to lake, holiday rental in Jamestown
Unit A  - 2 queen beds, 1 full bath, sleeper sofa, close to lake, holiday rental in Jamestown

Unit A - 2 queen beds, 1 full bath, sleeper sofa, close to lake

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Renovated Cabin near Wolf Creek Marina & multiple boat ramps w/ full kitchen, holiday rental in Jamestown
Renovated Cabin near Wolf Creek Marina & multiple boat ramps w/ full kitchen, holiday rental in Jamestown
Renovated Cabin near Wolf Creek Marina & multiple boat ramps w/ full kitchen, holiday rental in Jamestown

Renovated Cabin near Wolf Creek Marina & multiple boat ramps w/ full kitchen

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!, holiday rental in Jamestown
New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!, holiday rental in Jamestown
New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!, holiday rental in Jamestown

New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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B - New near Jamestown Dock, holiday rental in Jamestown
B - New near Jamestown Dock, holiday rental in Jamestown
B - New near Jamestown Dock, holiday rental in Jamestown

B - New near Jamestown Dock

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Near Jamestown Dock - A, holiday rental in Jamestown
New Near Jamestown Dock - A, holiday rental in Jamestown
New Near Jamestown Dock - A, holiday rental in Jamestown

New Near Jamestown Dock - A

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy camper at Wolf Creek RV Park, holiday rental in Jamestown
Cozy camper at Wolf Creek RV Park, holiday rental in Jamestown
Cozy camper at Wolf Creek RV Park, holiday rental in Jamestown

Cozy camper at Wolf Creek RV Park

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Cozy, stylish cabin 2 mins away from Cumberland Lake!, holiday rental in Jamestown
Cozy, stylish cabin 2 mins away from Cumberland Lake!, holiday rental in Jamestown
Cozy, stylish cabin 2 mins away from Cumberland Lake!, holiday rental in Jamestown

Cozy, stylish cabin 2 mins away from Cumberland Lake!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy Cumberland Cottage in Jamestown, KY! Only 2-miles from the marina!, holiday rental in Jamestown
Cozy Cumberland Cottage in Jamestown, KY! Only 2-miles from the marina!, holiday rental in Jamestown
Cozy Cumberland Cottage in Jamestown, KY! Only 2-miles from the marina!, holiday rental in Jamestown

Cozy Cumberland Cottage in Jamestown, KY! Only 2-miles from the marina!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Secluded Jamestown Cabin w/ Fire Pit!, holiday rental in Jamestown
Secluded Jamestown Cabin w/ Fire Pit!, holiday rental in Jamestown
Secluded Jamestown Cabin w/ Fire Pit!, holiday rental in Jamestown

Secluded Jamestown Cabin w/ Fire Pit!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lovely private cabin at Wolf Creek Marina sleeps 6, holiday rental in Jamestown
Lovely private cabin at Wolf Creek Marina sleeps 6, holiday rental in Jamestown
Lovely private cabin at Wolf Creek Marina sleeps 6, holiday rental in Jamestown

Lovely private cabin at Wolf Creek Marina sleeps 6

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Kentucky Coal Cabin 2 min from Lake Cumberland and Wolf Creek Dam, holiday rental in Jamestown
Kentucky Coal Cabin 2 min from Lake Cumberland and Wolf Creek Dam, holiday rental in Jamestown
Kentucky Coal Cabin 2 min from Lake Cumberland and Wolf Creek Dam, holiday rental in Jamestown

Kentucky Coal Cabin 2 min from Lake Cumberland and Wolf Creek Dam

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11, holiday rental in Jamestown
Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11, holiday rental in Jamestown
Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11, holiday rental in Jamestown

Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Lake Cumberland, minutes from Jamestown dock!, holiday rental in Jamestown
Lake Cumberland, minutes from Jamestown dock!, holiday rental in Jamestown
Lake Cumberland, minutes from Jamestown dock!, holiday rental in Jamestown

Lake Cumberland, minutes from Jamestown dock!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Close to Jamestown Marina -5-7  min drive, holiday rental in Jamestown
Close to Jamestown Marina -5-7  min drive, holiday rental in Jamestown
Close to Jamestown Marina -5-7  min drive, holiday rental in Jamestown

Close to Jamestown Marina -5-7 min drive

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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New Rustic Home Near State Dock, holiday rental in Jamestown
New Rustic Home Near State Dock, holiday rental in Jamestown
New Rustic Home Near State Dock, holiday rental in Jamestown

New Rustic Home Near State Dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lake Cumberland Cabin w/ Views & Fishing, holiday rental in Jamestown
Lake Cumberland Cabin w/ Views & Fishing, holiday rental in Jamestown
Lake Cumberland Cabin w/ Views & Fishing, holiday rental in Jamestown

Lake Cumberland Cabin w/ Views & Fishing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW!!The Overlook * Harbor Springs-2 miles from Jtown Marina! Lake View+Parking!, holiday rental in Jamestown
NEW!!The Overlook * Harbor Springs-2 miles from Jtown Marina! Lake View+Parking!, holiday rental in Jamestown
NEW!!The Overlook * Harbor Springs-2 miles from Jtown Marina! Lake View+Parking!, holiday rental in Jamestown

NEW!!The Overlook * Harbor Springs-2 miles from Jtown Marina! Lake View+Parking!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Endless Summer Getaway - 1 mile away from Jamestown Marina!, holiday rental in Jamestown
Endless Summer Getaway - 1 mile away from Jamestown Marina!, holiday rental in Jamestown
Endless Summer Getaway - 1 mile away from Jamestown Marina!, holiday rental in Jamestown

Endless Summer Getaway - 1 mile away from Jamestown Marina!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Time Cottage, 3 Bedroom 2 Bath, <3 Mile from Jamestown, holiday rental in Jamestown
Lake Time Cottage, 3 Bedroom 2 Bath, <3 Mile from Jamestown, holiday rental in Jamestown
Lake Time Cottage, 3 Bedroom 2 Bath, <3 Mile from Jamestown, holiday rental in Jamestown

Lake Time Cottage, 3 Bedroom 2 Bath, <3 Mile from Jamestown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cocktail Cove 4 bedroom 2 bath by Jamestown Marina, holiday rental in Jamestown
Cocktail Cove 4 bedroom 2 bath by Jamestown Marina, holiday rental in Jamestown
Cocktail Cove 4 bedroom 2 bath by Jamestown Marina, holiday rental in Jamestown

Cocktail Cove 4 bedroom 2 bath by Jamestown Marina

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Brand New Lake Cumberland Cottage Jamestown, KY, holiday rental in Jamestown
Brand New Lake Cumberland Cottage Jamestown, KY, holiday rental in Jamestown
Brand New Lake Cumberland Cottage Jamestown, KY, holiday rental in Jamestown

Brand New Lake Cumberland Cottage Jamestown, KY

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Harbor Hilltop at Cumberland, holiday rental in Jamestown
Harbor Hilltop at Cumberland, holiday rental in Jamestown
Harbor Hilltop at Cumberland, holiday rental in Jamestown

Harbor Hilltop at Cumberland

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dream cabin  with mancave and views of Lake Cumberland., holiday rental in Jamestown
Dream cabin  with mancave and views of Lake Cumberland., holiday rental in Jamestown
Dream cabin  with mancave and views of Lake Cumberland., holiday rental in Jamestown

Dream cabin with mancave and views of Lake Cumberland.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!, holiday rental in Jamestown
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!, holiday rental in Jamestown
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!, holiday rental in Jamestown

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury Cottage with pool 2.1 miles from beautiful Lake Cumberland -#2, holiday rental in Jamestown
Luxury Cottage with pool 2.1 miles from beautiful Lake Cumberland -#2, holiday rental in Jamestown
Luxury Cottage with pool 2.1 miles from beautiful Lake Cumberland -#2, holiday rental in Jamestown

Luxury Cottage with pool 2.1 miles from beautiful Lake Cumberland -#2

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Cottage with pool, 2.1 miles from beautiful Lake Cumberland, holiday rental in Jamestown
Luxury Cottage with pool, 2.1 miles from beautiful Lake Cumberland, holiday rental in Jamestown
Luxury Cottage with pool, 2.1 miles from beautiful Lake Cumberland, holiday rental in Jamestown

Luxury Cottage with pool, 2.1 miles from beautiful Lake Cumberland

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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THE LINKVIEW GETAWAY 4 bed/2 bath. 3 m to Jamestown Marina. 1 m from town square, holiday rental in Jamestown
THE LINKVIEW GETAWAY 4 bed/2 bath. 3 m to Jamestown Marina. 1 m from town square, holiday rental in Jamestown
THE LINKVIEW GETAWAY 4 bed/2 bath. 3 m to Jamestown Marina. 1 m from town square, holiday rental in Jamestown

THE LINKVIEW GETAWAY 4 bed/2 bath. 3 m to Jamestown Marina. 1 m from town square

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hidden Woods Cottage - Jamestown, Boat Parking & Pet friendly, holiday rental in Jamestown
Hidden Woods Cottage - Jamestown, Boat Parking & Pet friendly, holiday rental in Jamestown
Hidden Woods Cottage - Jamestown, Boat Parking & Pet friendly, holiday rental in Jamestown

Hidden Woods Cottage - Jamestown, Boat Parking & Pet friendly

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great place to gather near Lake Cumberland, holiday rental in Jamestown
Great place to gather near Lake Cumberland, holiday rental in Jamestown
Great place to gather near Lake Cumberland, holiday rental in Jamestown

Great place to gather near Lake Cumberland

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 58
Frequently Asked Questions about Jamestown