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House vacation rentals in Jamestown

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Top-rated house rentals in Jamestown

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An outdoor seating area is presented on a wooden deck overlooking a serene lake view. Comfortable furniture, including a sofa and chairs, surrounds a glass-topped table. An umbrella provides shade, and a small fire pit adds to the inviting space amidst greenery.

Home in Somerset

4.87 out of 5 average rating, 150 reviews

Lakeview Blue

You will not find a better view of Lake Cumberland! Newly renovated 2022!! Previously our family home, we cherish this property. We ask anyone renting to respect the neighbors and home as we have. The Lakeview Blue House is within walking distance of Lake Cumberland, several restaurants, gas stations and a liquor store. There is a seasonally open public boat ramp directly over the hill from the home and many others including Waitsboro, Burnside Marina and Burnside Island State Park/ ramp nearby.

The cozy living room features a mix of modern and rustic design elements. A dark leather sofa faces a stone fireplace, flanked by two bright armchairs. Natural light pours in through multiple windows, highlighting wooden beams and rich wall textures, creating a warm gathering space.

Home in Monticello

4.92 out of 5 average rating, 182 reviews

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

Top guest favorite

A spacious living area features a modern sofa with decorative pillows. Large opening doors showcase views of the covered porch and surrounding greenery, allowing natural light to fill the space. A wall-mounted television and fireplace are also present, enhancing the inviting atmosphere.

Home in Somerset

4.97 out of 5 average rating, 111 reviews

Garage Door to the Wilderness!

Welcome to this stylish and sleek tiny home that's perfect for modern living! With ample space to sleep 4, features a bathroom complete with a beautifully tiled custom shower. The kitchen is a chef’s delight, black cabinetry and elegant granite counters.Enjoy the seamless flow of heated tile flooring throughout, leading you to the covered back porch where you can sip your morning coffee! The back garage door offers easy access to nature’s beauty. Located 5 minutes from either town or the lake!

Top guest favorite

An outdoor seating area is arranged around a fire pit, with chairs positioned for comfort. The night sky glows softly from the moonlight, casting a gentle light on the surroundings. Trees are faintly visible in the background, enhancing the serene atmosphere.

Home in Bronston

4.99 out of 5 average rating, 128 reviews

Countryside getaway near Conley & Burnside

Welcome to our countryside getaway nestled on almost 5 acres within 5-20 miles of Burnside, Lee's Ford, and Conley Bottom Marinas. Enjoy the day on Lake Cumberland. Come back to relax, eat, drink & be merry. Gather around the outside barbecue area and fire pit or snuggle up inside next to the fireplace, playing games or watching a movie. Whether you are on a couple's retreat, fishing buddy's getaway, or family vacation - the house and outdoor area provide plenty of room to relax and enjoy.

Top guest favorite

A spacious living area features a large leather sectional sofa and a teal armchair, complemented by a decorative ottoman. A flat-screen television is mounted on the wall opposite a large window, with natural light illuminating the light wood flooring.

Home in Jamestown

5 out of 5 average rating, 12 reviews

Lake Vibes

Your Lake Cumberland retreat! Located just minutes from Lake Cumberland, this home offers the perfect escape for your next getaway. Located just 2 miles from Jamestown Marina, with easy boat access and great proximity to fantastic restaurants, and recreation, this is the perfect spot for those who love the outdoors, adventure, or relaxation! The home offers a horseshoe drive for an easy in and out, and features a garage on site for boat storage, as well as an out building, both with electric.

Top guest favorite

The exterior of a modern blue house is showcased, featuring multiple large windows that allow natural light to enter. A freshly paved driveway leads up to the home, while a sign indicating the house number is positioned nearby. Lush greenery surrounds the property.

Home in Jamestown

5 out of 5 average rating, 20 reviews

The Bourbon House

Take it easy at this unique Kentucky Bourbon themed getaway only 10 minutes away from Lake Cumberland via the Jamestown Marina. The Bourbon House has two queen beds in their own bedrooms and a full sized pull out sofa with 2 full bathrooms. It has a fully equipped kitchen but is only 5 minutes away from Jamestown Square with 3 different delicious restaurant options. Enjoy the peace of being in the country on the back patio facing the woods, with a fire in the fire pit.

Top guest favorite

The cottage features a green metal roof and a welcoming front porch with multiple wooden rocking chairs. Two planters are positioned at either side of the entrance, and a outdoor grill is visible near the porch. A gravel path leads up to the door, with lush greenery in the background.

4.94 out of 5 average rating, 134 reviews

Avery Acres

Country setting located 2 miles from Lake Cumberland with 3 boat ramps within an 8 mile drive. Fryman landing closest ramp to 76 Falls 2 miles,Marina @ Rowena 5.8 miles,Carter Dock Road 7.8 miles. Within 20 minute drive Grider Hill Marina and 1/2 hour drive to Dale Hollow Lake. Fire pit and outdoor gas grill supplied. We are on central time zone check in time is 4:00 PM and checkout is 11:00 AM We are pet friendly however there is a fee of $50 with a 2 pet limit.

The kitchen features a modern design with white cabinets and granite countertops. Stainless steel appliances are showcased, alongside open shelving displaying various dishware. Four blue metal stools are positioned around the kitchen island, and a window allows natural light to enter.

Home in Jamestown

4.9 out of 5 average rating, 60 reviews

Lake Life Dot Calm (Slip Available)

Welcome to your new peaceful retreat less than 2 miles from Jamestown Marina and Lilly Creek boat ramp. SLIP RENTAL available. ROOM TO PARK your boat and trailer in the driveway! Take a walk down the street (or ride one of our bikes) to see gorgeous lake views! This 3 bedroom, 3 bathroom house has what you need for your stay! Each bedroom has its own full bathroom. Remodeled kitchen, game room in the garage, smart TVs, great back deck, and much more!

A charming cottage is set among greenery, featuring a spacious deck with a pergola. A well-maintained yard provides a sunny space, with trees offering shade and privacy. An outside staircase connects the deck to the lower level, adding accessibility to the home.

Home in Russell Springs

4.8 out of 5 average rating, 241 reviews

Driftwood Cottage with HotTub on Lake Cumberland

Gorgeous cottage with seasonal lake view overlooking Lake Cumberland . The Marina which has boat slips, boat dock , boat rentals and restaurant are a quick jog down the hill. Enjoy the lake view from the Hot tub on the deck,amazing on even a winter day! The home has a big yard with trees for privacy . 2 bedrooms on main floor. Loft has 1 bedroom plus a day bed with trundle in open area overlooking downstairs. Outside staircase and inside spiral stairs

Top guest favorite

Home in Jamestown

5 out of 5 average rating, 57 reviews

Midnight Pearl

A mountain modern luxurious home designed for a couples' getaway features sleek, contemporary architecture offering stunning mountain 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.

A spacious outdoor deck is illuminated with warm lighting, featuring a large bar area with high-top chairs. A cozy seating area with additional chairs is visible, surrounded by trees, creating a peaceful atmosphere for relaxation in the evening.

Home in Jamestown

4.88 out of 5 average rating, 26 reviews

Harbor Hilltop at Cumberland

Lake Cumberland Retreat | Near Safe Harbor Marina Relax at this peaceful cottage just steps from Safe Harbor Marina and 6 minutes from Lily Creek boat ramp. This 3-bedroom, 2-bath home sleeps 8 guests with 5 beds and has boat parking. Unwind on the huge deck, screened porch, or by the fire pit in a quiet neighborhood. Perfect for fishing, boating, or just enjoying the lake. Book your stay today!

Top guest favorite

Home in Science Hill

4.97 out of 5 average rating, 117 reviews

TT’s Treehouse

Cozy studio guesthouse with beautiful oak vaulted ceiling overlooking scenic woods and creek just 10-15 minutes from boat ramp on Lake Cumberland. Covered porch around guesthouse with gas grill access. Kitchen fully stocked. Full size sofa couch, and 2 full size floor mattresses in loft. Free wifi available. Onsite boat parking available. Fire pit and fire table available-both outside. No smoking.

Vacation rentals for every style

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Cabins

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Hotels

Stylish accommodations with great services and amenities

Unique stays

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Popular amenities for Jamestown house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

Home in Monticello

5 out of 5 average rating, 11 reviews

Cumberland Belle Lakehouse-5bedrm,10bed,5bath

The exterior of the cottage displays a covered porch with comfortable seating for relaxation. A propane grill is situated nearby on a concrete patio, surrounded by landscaping featuring black stones. The cottage is framed by green grass and a clear blue sky, enhancing the outdoor space.

Home in Somerset

5 out of 5 average rating, 4 reviews

White Oak Cottage - Resort Pool, Boat Slip

A private pool is set against a lush, green backdrop, surrounded by blue adirondack chairs for relaxation. The clear water reflects the sky, while a well-maintained patio area is featured, offering scenic views of the nearby waterfront.

Home in Monticello

4.74 out of 5 average rating, 57 reviews

Private pool and hot tub overlooking the Lake !

A comfortable living area is presented, featuring a gray sofa adorned with throw pillows. A round wooden table occupies the center, topped with decorative items, including a lamp and a small book. Light filters through sheer curtains, highlighting the patterned area rug.

Home in Burnside

4.9 out of 5 average rating, 10 reviews

Kellerman’s at VillagerResort-Pool, Boat slip/dock

A spacious living area is highlighted by a high vaulted ceiling and a striking spiral staircase. Light-colored furnishings and neutral walls create an open atmosphere, while natural light floods through large windows, showcasing a cozy seating arrangement and a central coffee table.

Home in Burnside

4.89 out of 5 average rating, 57 reviews

Hillside Haven (108E) Fun, Lake, Golf carts, Pool

A spacious patio area features a large smoker and gas grill. In the background, an in-ground pool is visible, complete with a slide and surrounded by a secure fence. Lush trees provide shade, and the sky is clear with a hint of blue.

Home in Somerset

5 out of 5 average rating, 4 reviews

Cumberland Classic/Boat Ramp/Private Pool/Bar/City

A charming white bungalow is framed by a well-maintained lawn and colorful flower beds. A red roof adds a pop of color, and the welcoming entrance features a brick pathway leading to the front door. American flags adorn the porch, enhancing the inviting exterior.

Home in Somerset

4.83 out of 5 average rating, 23 reviews

Burnside Bungalow, w/ dock, pool & firepit

Top guest favorite

A screened-in porch features comfortable seating, including a sectional sofa and decorative pillows. A coffee table is positioned in the center, complemented by a small refrigerator and a lamp. Large windows offer views of the surrounding nature, and ceiling fans provide ventilation.

Home in Pulaski County

5 out of 5 average rating, 19 reviews

Lake-Front Woodson Bend 14-1

Weekly house rentals

A charming cottage is nestled among greenery, offering a welcoming porch with seating. The roof is designed with a warm red hue that complements the natural surroundings. The mountains in the background provide a serene view, enhancing the outdoor atmosphere.

Home in Whitley City

5 out of 5 average rating, 3 reviews

Lake Cumberland Forest Cottage!

Home in Greensburg

4.96 out of 5 average rating, 27 reviews

Hillview Haven

A modest green house is situated on a grassy lawn, featuring a flat front yard. Steps lead to a welcoming porch with two red chairs, inviting relaxation. The house is framed by a large tree, and a clear sky can be seen above.

Home in Highway

4.95 out of 5 average rating, 55 reviews

Little Green House of Shipley

The charming lake house is situated on a gently sloping hill, surrounded by tall trees with vibrant autumn foliage. A spacious wrap-around deck encircles the home, providing a great outdoor area for relaxation. The exterior features a combination of stone and siding, enhancing its natural appeal.

4.9 out of 5 average rating, 79 reviews

Waterfalls, fishing pond, lake view, and 8 acres!

Top guest favorite

The exterior view showcases a well-maintained brick home set on a grassy lawn. A flagpole stands prominently, flanked by lush trees, with fields visible in the background under a clear blue sky. The asphalt driveway leads to a garage, emphasizing the property's spaciousness.

Home in Columbia

5 out of 5 average rating, 26 reviews

Three-A Hideaway

Top guest favorite

A charming yellow house is situated on a grassy area near a tranquil body of water. The property displays a green metal roof and features a small patio with a black table and chairs. Nearby trees provide shade and natural beauty.

Home in Monticello

4.96 out of 5 average rating, 56 reviews

Vacationers delight at Conley Bottom

The exterior of a stylish Barndaminium is showcased, featuring a blue metal siding and large glass garage door. Two stories are visible, with evenly spaced windows and a welcoming front porch adorned with seating. Green grass and trees frame the property, reflecting a serene environment.

Home in Russell Springs

5 out of 5 average rating, 22 reviews

NEW 4br 3ba Barndo Overlooking Lake Cumberland

Top guest favorite

Home in Monticello

5 out of 5 average rating, 14 reviews

Cozy Countryside Cottage at Lake Cumberland

Private house rentals

Top guest favorite

The exterior view of Fawn Run showcases a spacious covered porch featuring seating arrangements for relaxation. The property is surrounded by trees, providing a sense of seclusion, while a grassy area extends in front of the home, enhancing its natural appeal.

5 out of 5 average rating, 21 reviews

Fawn Run on Lake Cumberland

Top guest favorite

The log cabin is set among tall trees, featuring a spacious deck with seating. Red accents highlight the windows, contrasting with the natural wood finish. The serene surroundings suggest a peaceful retreat, with glimpses of green foliage and the water visible in the background.

Home in Bronston

4.97 out of 5 average rating, 34 reviews

Lowe Tide Log Cabin-2 story plus loft water view

Top guest favorite

A newly remodeled single-story home features a welcoming front porch with wooden railings. The exterior is complemented by a metal roof and large windows, allowing natural light to fill the interior. Lush greenery surrounds the property, enhancing its inviting appearance.

Home in Jamestown

5 out of 5 average rating, 11 reviews

Linkview Getaway | Boat Parking

An outdoor deck area features a wooden table complemented by an orange lantern and a rustic gray lantern. Lush green trees provide a natural backdrop, and a glimpse of the lake is visible in the distance under a clear blue sky.

Home in Wayne County

4.94 out of 5 average rating, 32 reviews

Lake House "Dar Bida" Monticello

Home in Jamestown

4.74 out of 5 average rating, 81 reviews

Twin Creeks Retreat!

Top guest favorite

The exterior of the home features a well-maintained lawn with greenery surrounding a decorative sign. A welcoming door in a warm tone is complemented by white trim and multiple windows. A light fixture hangs near the entrance, illuminating the pathway.

Home in Columbia

4.94 out of 5 average rating, 89 reviews

Clayton House

Top guest favorite

The charming farmhouse features a welcoming exterior with a covered front porch, two rocking chairs, and a decorative sign. A well-maintained lawn frames the entrance, while the home is adorned with an American flag and surrounded by neatly arranged shrubbery.

Home in Russell Springs

5 out of 5 average rating, 112 reviews

Gran's Place

Home in Somerset

4.75 out of 5 average rating, 28 reviews

Cumberland Cottage

Quick stats about house rentals in Jamestown

Total rentals
20 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
20 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

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