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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

4.86 out of 5 average rating, 148 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.

A cottage is seen surrounded by vibrant autumn foliage, with a gravel driveway leading to the entrance. The architecture features a gabled roof and a spacious front porch, providing an inviting entry point to the home.

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, 107 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, 124 reviews

Lake Cumberland 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 charming country house is depicted, featuring a red metal roof and a welcoming porch. Two chairs are placed on the porch, overlooking a grassy yard. The backdrop reveals gentle hills under a clear blue sky, creating a serene outdoor setting.

Home in Knifley

4.99 out of 5 average rating, 101 reviews

The ranch house. Relax and unwind

Quiet, peaceful, country setting. There are country roads for walking and bike riding. For the boaters and fishermen, we are just minutes away from Arnold’s landing boat ramp and also Holmes Bend marina on beautiful Green River lake. For the hunting enthusiast, there are 20,000 plus acres of public land available for spring and fall hunting, with an abundance of turkey and deer. Close to Campbellsville University and Lindsey Wilson in Columbia. Lake Cumberland is also a short drive away.

A historic farmhouse features a welcoming front porch with seating. Steps lead from a wooden walkway to the entrance, surrounded by well-maintained greenery and flower beds. The building showcases a metal roof and traditional white siding, providing charm and character.

Home in Russell Springs

4.77 out of 5 average rating, 151 reviews

The Little FarmHouse

Historic farmhouse in a peaceful country setting. Home was built by World war 2 veteran! Kitchen has all your basic needs ;Crock pot, Coffee maker and toaster , washer and dryer for your convenience! The bathroom and one bedroom is on main floor and upstairs are 2 more bedrooms plus a tiny sunroom with a daybed and a trundle bed that’s great for kids. Lovely front porch where wildlife can often be seen! Convenient location with driveway right off of HWY 80 and 5 miles from town

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.

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, 132 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, 58 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 rustic home with a metal roof features a spacious porch that wraps around its exterior. Stairs lead up to the main entrance, and the porch offers areas that are screened in. A gravel area is visible at the front, providing parking space.

Home in Jamestown

4.82 out of 5 average rating, 68 reviews

New Rustic home near State Dock!

Great getaway! 1 mile from State Dock entrance. This new rustic home has 3 bd, 2 bath, open kitchen, fireplace in living room, loft master bedroom, full wrap around porch with a partial screened in area with great views. We have a nice size covered porch to relax and enjoy something on the grill. This home has parking for multiple vehicles or even for a boat. Come check out our lovely home to make your lake days memorable!

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!

Vacation rentals for every style

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Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Jamestown house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Burnside

4.79 out of 5 average rating, 75 reviews

Majestic View (6E) View, Fun, Lake, Pool

The two-story building features a welcoming yellow entrance and expansive covered decks on both levels. A gravel driveway leads up to the property, with trees lining the background and a soft sunset sky providing a warm backdrop.

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 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, 3 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

An aerial view captures the clubhouse area featuring a large swimming pool surrounded by sunbathers. Nearby, two tennis courts and playground equipment are visible, along with a grassy area bordered by trees. Several parked cars and walkways suggest access to various amenities.

Home in Pulaski County

5 out of 5 average rating, 19 reviews

Lake-Front Woodson Bend 14-1

Weekly house rentals

Top guest favorite

A living room features fully reclining furniture arranged around a patterned rug. Two lamps illuminate the cozy seating area. A wall sign reads 'LAKE LIFE.' An open view leads to the dining area, which is visible through a wide entryway.

Home in Russell Springs

5 out of 5 average rating, 33 reviews

Ina's Place

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, 87 reviews

Clayton House

The exterior of a charming home showcases a welcoming front porch with two black rocking chairs. Lush greenery and neatly arranged flower beds enhance the inviting entrance. A pathway leads to the door, with a vast lawn extending in the background under a clear blue sky.

Home in Monticello

4.88 out of 5 average rating, 25 reviews

Cozy farmhouse close to lake!

A charming house is set against a backdrop of lush greenery, surrounded by tall trees. The well-maintained lawn features a manicured appearance, while the welcoming front porch is highlighted by a red entry mat. A clear blue sky complements the serene forest setting.

4.89 out of 5 average rating, 76 reviews

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

Top guest favorite

The exterior of a single-story home features a green metal roof and light beige siding. A wooden deck with steps leads to the front door, flanked by large windows. Trees provide shade on the front lawn, and landscaped areas enhance the entryway.

Home in Elk Horn

5 out of 5 average rating, 11 reviews

Linny’s Landing

Top guest favorite

A spacious wooden deck showcases a hot tub with jets, surrounded by outdoor seating, including chairs arranged in a circle. The backdrop features a peaceful landscape of trees and open pasture, with soft evening light enhancing the serene atmosphere.

5 out of 5 average rating, 25 reviews

Near Lake! Hot Tub + King Suite + Fire Pit +Arcade

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, 21 reviews

NEW 4br 3ba Barndo Overlooking Lake Cumberland

A bright blue cabin exterior is complemented by a spacious wrap-around deck, featuring two wooden lounge chairs and an outdoor grill. Natural wood decking showcases an inviting space for relaxation, while large windows provide views of surrounding trees.

4.77 out of 5 average rating, 60 reviews

Little blue house on the lake

Private house rentals

The open-concept kitchen and dining area blend seamlessly with the living space. Features include wooden cabinetry, a stone island with seating, and modern appliances. Natural light illuminates the area, showcasing a cozy seating arrangement by a striking stone fireplace.

5 out of 5 average rating, 20 reviews

Fawn Run on Lake Cumberland

Top guest favorite

A newly constructed duplex is showcased against a vibrant sunset, with a metal roof and a spacious porch. The surrounding grassy area is bordered by leafless trees, providing a serene outdoor setting. A gravel driveway leads up to the entrance, enhancing accessibility.

Home in Campbellsville

5 out of 5 average rating, 44 reviews

The Last Cast Unit A

Top guest favorite

A wooden deck with a sturdy railing offers a view of trees and a calm river. The landscape is framed by lush greenery, enhancing the peaceful outdoor setting. The sky is overcast, adding a serene ambiance to the scene.

Home in Bronston

4.97 out of 5 average rating, 34 reviews

Lowe Tide Log Cabin-2 story plus loft water view

A cozy living area features two olive green sofas adorned with decorative pillows. A coffee table sits at the center, accompanied by a basket of throws. A large artwork of a rooster hangs on the wall, alongside nature-themed prints. Soft lighting is provided by table lamps.

Home in Columbia

4.92 out of 5 average rating, 50 reviews

Abells Spring Branch

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

4.93 out of 5 average rating, 29 reviews

Lake House "Dar Bida" Monticello

Top guest favorite

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

4.96 out of 5 average rating, 53 reviews

Little Green House of Shipley

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

Top guest favorite

The exterior of the home features a welcoming porch with outdoor seating, surrounded by lush greenery. A paved driveway leads to the garage, with ample grassy area nearby. The architecture includes a combination of brick and siding, complemented by a clear blue sky overhead.

Home in Columbia

5 out of 5 average rating, 23 reviews

Three-A Hideaway

Quick stats about house rentals in Jamestown

Total rentals
20 properties
Nightly prices starting at
G$20,913 GYD 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