Home Vacation Home Rentals By Owner In Jamestown, KY

Showing 20 Of 41 Vacation Rentals
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Exceptional(8)

$246.02

/ Nightly
Private Vacation Home

Luxury Retreat Near Lake Cumberland and Minutes to Marina, Dam & Boat Launch

Jamestown, Kentucky, United States

A mountain modern luxurious home designed for a couples' getaway features sleek, contemporary architecture offering stunning woodland views. Inside, a spacious living room boasts a cozy, modern fireplace, while outside, multiple fire pits create intimate, warm spaces under the stars. The interior is adorned with high-end finishes, blending natural wood and stone elements for a serene, upscale retreat.brbrThis stunning home features two spacious bedrooms, each equipped with a fireplace and flat-screen TV, you'll find warmth and entertainment at your fingertips. brbrThe two elegant bathrooms boast cutting-edge Bluetooth features, elevating your daily routine with modern convenience.brbrThe heart of the home is the open-concept living room and kitchen, designed to foster connection and comfort, with large windows that showcase breathtaking views.brbrOutside, the property truly shines. A wraparound deck embraces the home, providing multiple spots to relax and take in the surrounding nature. Off the master bedroom, a private sitting area waits for quiet moments. On the back deck, you'll find a sleek modern fire pit, the perfect spot for sipping your morning coffee or enjoying a glass of wine at sunset.brbrFor those seeking outdoor adventure and relaxation, a custom fire pit, designed for making s’mores and stargazing, sits surrounded by nature, offering a cozy retreat under the stars. This home is your woodland sanctuary, blending luxury with the peaceful beauty of nature.brbrProvided amenities:br- One-use paper products br- Shampoo, conditioner, body wash, and hand soap br- Linens and Towelsbr- Cornhole boardsbr- Blackstone GrillbrbrYou’re in the heart of the woods. Expect the sounds, sights, and occasional visitors that make this place special. We maintain regular pest control, but nature is part of the experience.brbrThis location is minutes away from Lake Cumberland State Resort Park and Marina and Halcombs Landing Boat Ramp 'Dam' with easy access to the water.brbrThe parking space has room for boat parking.
Bed 2

Bed

Bath 2

Bath

Sleep 4

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Exceptional(15)

$344.5

/ Nightly
Private Vacation Home

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

Jamestown, Kentucky, United States

This charming 3 bedroom, 2 bath lake house has an adorable open cottage feel and is the perfect place to enjoy a relaxing, fun getaway at Lake Cumberland. The house tucks back in the private roads of Harbor Springs, a neighborhood watch community. Has large concrete drive way spacious for several cars and/or a boat. Less than 3 miles from Jamestown Marina which allows guests to be on the water in no time. Also 20 minutes away from State Park and State Dock Marina. brbrThe house comes fully furnished with all the day to day amenities so you can leave your worries at home. Master bedroom on first floor with a King size bed and bathroom. Two bedrooms upstairs, one with two queen beds, one with one queen size bed and both share a connecting bathroom. Full kitchen with all your cooking and eating needs, including a griddle, quesadilla, waffle and tea maker. Guests will enjoy: a restful night on comfy linens, plush bath towels, a large couch with chase lounge, Wifi and Roku TV's in every room. Washer and dryer is provided and bathrooms come stocked with shampoo, conditioner and body wash.brbrFront porch faces the lake and provides seating for two (spacious for more) to enjoy the warm sun and partial view of the lake, overlooking Jamestown and Stock Dock Marina. Screen enclosed patio with comfy seating and an extra dining table to enjoy meals outside, worry free of bugs. Outside patio also has a TV for those needing their additional space to unwind. Also a perfect area to put feet up, enjoy a cup of coffee in the morning with the sun rise, or glass of wine at night with the sun set. Either one, both will get the joy of listening to nature sounds. br brRainy day no worries. Enjoy playing cards, board games or watch your favorite Netflix, Hulu or Amazon shows. Whether your here for the weekend or a week, this house will be perfect for your visit to Lake Cumberland.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

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Exceptional(12)

$494.44

/ Nightly
Private Vacation Home

Lake Cumberland Retreat w/ Deck & Views!

Jamestown, Kentucky, United States

4,746 Sq Ft | Family Friendly | Home Gym | Multi-Level DeckbrbrThis spacious 6-bed, 5-bath Jamestown vacation rental boasts plenty of space for everyone to come along on your next Lake Cumberland adventure! Spend warm summer days with the family out on the water, then unwind in the evenings on the multi-level deck. Dinner is easy with a fully equipped kitchen, dining table, and gas grill on-site, or you can visit a local restaurant nearby.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbrbr- Bedroom 1: 1 king bed br- Bedroom 2 (Office): 1 twin daybed br- Bedroom 3: 2 full beds, 2 bunk beds (full & twin)br- Bedroom 4: 1 queen bed br- Bedroom 5: 1 full bed, 1 twin bed, 2 bunk beds (twin)br- Bedroom 6: 1 king bed, 1 twin bed, 1 bunk bed (twin)br- Additional Sleeping: 1 cribbrbrINDOOR LIVINGbr- Hardwood floors, vaulted ceilingsbr- Wood-burning fireplacesbr- Smart TVs w/ cable, DVD playerbr- Board games, booksbr- Home theatre systembr- En-suite bathroom w/ jetted tubbr- Central A/C + heating, ceiling fansbrbrOUTDOOR LIVINGbr- Lake views, private yardbr- Multi-level deck, gas grillbr- 2 dining areas, ceiling fanbr- Loungersbr- Fire pit, bicyclesbrbrKITCHENbr- Fully equipped, dishwasher, stove/ovenbr- Drip coffee maker, hot water pot, ice makerbr- Refrigerator, microwavebr- Blender, toaster, spices br- Dishware/flatware, high chairbr- Separate kitchenettebrbrGENERALbr- Free WiFibr- Hair dryer, complimentary toiletriesbr- Washer & dryer, laundry detergent br- Iron/board, linens/towelsbrbrFAQbr- 1 exterior security camera (Ring doorbell, facing out)brbrACCESSIBILITYbr- 1 step required for accessbr- 3-story homebr- 2 bathrooms/2 bedrooms on 1st floor, accessible-height toilets brbrPARKINGbr- Driveway (6 vehicles)br- Boat parking allowed on-site (3 max)brbr-- THE LOCATION --brbr- Located on a spacious property with on-site access to Lake Cumberlandbr- 6 miles to Lake Cumberland Dragwaybr- 6 miles to Jamestown Marinabr- 33 miles to Dale Hollow Lakebr- 116 miles to Louisville International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- The 3-story property requires 1 step to enter and interior stairs to reach the basement and 2nd floorbr- Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed
Bed 6

Bed

Bath 5

Bath

Sleep 15

Sleeps

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Exceptional(1)

$154.34

/ Nightly
Private Vacation Home

The Lodge Lake Retreat – Family-Friendly with Private River Access

Jamestown, Kentucky, United States

Stylish Lake Retreat – Family-Friendly Getaway with Private River AccessbrWelcome to your perfect Cumberland River escape! This cozy and stylish 2-bedroom, 1-bath retreat is designed for comfort, making it an ideal spot for family vacations or a relaxing getaway with friends. With two bedrooms plus a pull-out sofa, the home sleeps up to 6 guests comfortably.brThe heart of the home is its bright, open-concept living, kitchen, and dining area. Whether you’re cooking meals together, playing games, or winding down after a day at the lake, there’s plenty of room for everyone to gather. For added convenience, the home is stocked with soap, shampoo, conditioner, and laundry essentials, including a washer and dryer with detergent provided. You’ll also find an iron and ironing board, as well as an air mattress to accommodate extra guests.brStep outside and enjoy the best of outdoor living. Relax on the large covered front porch with your morning coffee, unwind on the covered back porch in the evening, or gather around the fire pit to roast marshmallows under the stars. For adventure lovers, the property features private river access—perfect for fishing, kayaking, or simply enjoying the peaceful beauty of the Cumberland River.brTucked away on a quiet dead-end road, this retreat offers both privacy and convenience. You’ll be just 15 minutes from downtown Jamestown for local dining and shopping, and 15 minutes from Jamestown Marina for boating, swimming, and lake fun.brWhether you’re exploring the river, heading out on the lake, or simply spending time with loved ones, this retreat blends comfort, style, and family-friendly charm to create an unforgettable stay.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

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Exceptional(5)

$457.5

/ Nightly
Private Vacation Home

Lake View Home-Good for Big Group-Jamestown Marina

Jamestown, Kentucky, United States

Wake up to unbeatable views of Lake Cumberland and unwind with cocktails as you overlook the marina below. This 3BR/4BA home features two en-suite masters, a fun-filled bunk room, game room, and a dreamy back porch you have to see to believe. Just 7 minutes from Jamestown Marina, it's the perfect lake getaway for families, friends, and boaters alike.brbrThe Space:brLake Cumberland has always been our happy place! It has been a dream of ours to have a house with a view, and to share it with others interested in visiting the area!brbrThe main living space is an open concept living room, kitchen and dining space. Downstairs is also a pool table room where you can enjoy some games, beverages, etc.!brbrThe most amazing part of our home is the back porch and the view. We always say we bought it for the view and you will know why!! Pictures don’t do it justice.brbrThe property does not include a large yard space. However, there is a field directly across the street that you would be welcome to use for football, Frisbee, Cornhole, etc. There is a Cornhole set, giant beer pong game, and sidewalk chalk available for guest usebrbrThere is a gas grill (also an extra propane tank) and grilling tools for guest use.brbrThere is ample parking at this house. The two drives (upper and lower) can accommodate 6 cars comfortably, or 4 on the lower and a boat and trailer on the upper. **We do NOT recommend pulling a boat/trailer down the lower drive as it WILL scrape across the drive and potentially damage your vessel.brbrLast, if you are someone who works from home and need to get a few hours in while enjoying your trip- no worries, we've got you! In the upstairs master bedroom, there is a cloffice (closet turned office). This includes a desk, chair, and monitor for use as a second screen if needed.brbrGuest access:brGuests will have full access to the home minus a few locked owners closets. Guests will enter the home through the front door using a keypad lock. Your access code will be sent to you automatically prior to your stay.brbrOther things to note:brGuests coming with boats should note that the driveway will only accommodate a single boat at the top. There is a very sharp hill on both sides of the lower drive that may be difficult to get a boat down without causing damage. If there is more than one boat for the house, please let us know and we can recommend a place to park.
Bed 3

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Bath 3

Bath

Sleep 12

Sleeps

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Exceptional(38)

$510.48

/ Nightly
Private Vacation Home

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Jamestown, Kentucky, United States

Sunny days on the water await at this 4-bedroom, 3-bathroom vacation rental on Lake Cumberland! This home is nestled on 1 acre of wooded land and is just 10 minutes to Jamestown Marina. Boasting everything you need for a serene waterfront retreat with a screened-in deck, lake views, and outdoor dining, this home is perfect for your next worry-free vacation. When the sun sets, whip up a meal in the fully equipped kitchen or gather the group for a fun evening in the game room!brbr-- THE PROPERTY --brbr3,400 Sq Ft | Outdoor Fireplace | Private DockbrbrThe perfect retreat for families looking for a fun-filled vacation, this spacious home offers direct access to Lake Cumberland and ample outdoor entertainment space!brbrBedroom 1: King Bed, Twin Daybed | Bedroom 2: Full Bed, Futon | Bedroom 3: Twin/Full Bunk Bed w/ Twin Trundle | Bedroom 4: 2 Queen Beds | Living Room: Full Sleeper Sofa | Family Room: Full Sleeper Sofa, Full FutonbrbrOUTDOOR SPACE: Lake view, screened porch, charcoal grill, fireplace, furnished patio, dining tablebrINDOOR LIVING: 6 Smart TVs, video library, gas fireplace, jetted tub, dining table, pool table, air hockey, poker table, books, board games, ceiling fans, iPod/MP3 docking station, laptop-friendly workspace brKITCHEN: Fully equipped w/ cooking basics, kitchen island w/ seating, dishware/flatware, kettle, spices, toaster ovenbrGENERAL: Free WiFi, washer/dryer, linens/towels, iron/board, complimentary toiletries, air conditioning/heat, hair dryersbrFAQ: 4 exterior security cameras (facing dock, front, side, and back of home), steps required for accessbrFAMILY FRIENDLY: High chair, baby gate, playpen, changing table, basinetbrPARKING: Gravel driveway (4 vehicles)brbr-- THE LOCATION --brbrLAKE CUMBERLAND (on-site): Boating, swimming, watersports, bass fishing, 76 FallsbrMARINAS: Jamestown Marina (6.0 miles), Safe Harbor Jamestown (6.4 miles), Lake Cumberland State Dock (13.3 miles), Indian Hills Resort/Alligator II Marina (20.5 miles), Safe Harbor Grider Hill (26.2 miles), Marina Rowena (35.3 miles)brDRINK ‘N DINE: Jamestown Cafe (2.3 miles), Rey Azteca Mexican Grill Restaurant (2.6 miles), Giovanni's Pizza (2.9 miles), Reel Java & Creamery (5.0 miles), Creelsboro Country Store (13.1 miles)brAIRPORT: Louisville International Airport (116 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs and may be difficult for guests with limited mobilitybr- NOTE: RVs/trailers are not permitted at the property or on the road leading to the property at any timebr- NOTE: Your safety matters. This property features 4 exterior security cameras. Camera 1 is located on the front door, facing the front entry. Camera 2 is located on the upper deck, and camera 3 is located on the lower deck, both facing the back entryways. Camera 4 is located by the boat dock, facing the dock. They do not look into any interior spaces. The cameras do not record video or sound
Bed 4

Bed

Bath 3

Bath

Sleep 20

Sleeps

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Exceptional(121)

$288.83

/ Nightly
Private Vacation Home

Lake Cumberland Hideaway #2-1 Mile above Jtown Marina! Boat Parking & Fire Pit!

Jamestown, Kentucky, United States

We now have 4 amazing properties sitting above the Jamestown Marina & 2 boat ramps!brLocation, Location, Location... This amazing property is located one mile above Jamestown Resort & Marina and sits on a massive 1 acre lot surrounded by trees on 3 sides. It has a huge private drive located directly off of the main road (Kentucky 92) for all of your vehicles and boats. A picture says a thousand words so take a look at our pictures and see what we have put together for you! We love the open floor plan where the living room, kitchen and dining area are set up perfectly for entertaining or just relaxing. Check out the pictures of our comfy new sectional couch where everyone can chill, watch a movie or play games.. My favorite spot is the large covered deck where you can sit and drink your coffee while watching the sunrise or watch the abundance of wildlife. There is plenty of seating where you can gather with family & friends after boating or fishing and reflect on the days adventures, create new memories and always cook an awesome meal on the grill. The fire pit is located directly behind the house and is sitting on nearly an acre lot surrounded by trees. brbrIf you have ever stayed with us before you know we don't spare any expense when it comes to creating a luxurious place to stay with all the comforts of home! We want everyone to have a great experience while staying at one of our properties so please give feedback and let us know if you are not 100% satisfied..
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

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$246.94

/ Nightly
Private Vacation Home

THE LAKE NEST OFF JAMESTOWN SQUARE - Hot Tub, Grill, Sidewalk & Close to Lake

Jamestown, Kentucky, United States

Under NEW ownership & more pics coming soon! brbrNestled in the heart of Jamestown. Close to downtown & the lake! brbrWe invite you to come & enjoy THE LAKE NEST. Just walking distance of the town square & restaurants. Plus we are just 4 miles from Safe Harbor Jamestown Marina & 3 miles from the Lily Creek Boat ramp. Beautiful area of Lake Cumberland! brbrFeatures/Amenities: br- Hot Tub (5-person)br- 2 bedrooms (1 king & 1 queen)br- 1 queen sleeper sofa in the living roombr- 1 full bath (shower)br- Fully equipped kitchenbr- Living area with large flat screen TVbr- Washer & dryerbr- Free Wifibr- Plenty of parking for at least 3 boats/trailers br- Outdoor Grillbr- FirepitbrbrPolicies: br- NO smokingbr- NO petsbr- NO parties/events of any type such as bachelor, bachelorette, etc.br- Must be 23 years or older to reservebr- 1 security camera at the front door onlybrbrbrCheck out all our Lake Cumberland Vacation Rentals:br- The Lake House at Beaver Creek - only 1 mile from the Beaver Creek Marina in Monticello, Ky. Vrbo # 4629191brbr- The Beaver Creek Getaway - only 1 mile from Safe Harbor Beaver Creek Marina in Monticello, Ky. Vrbo # 4553133brbr- The Little Hideaway - only 1 mile from Safe Harbor Beaver Creek Marina in Monticello, Ky. Vrbo # 9474198brbr- The Lake Nest Off Jamestown Square - walking distance of town square & only 4 miles to Safe Harbor Jamestown Marina Vrbo # 5224773brbrHope you choose us for your next Lake Cumberland stay!brbrOur prices include all fees. No hidden fees.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps