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House vacation rentals in Jamestown

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Top-rated house rentals in Jamestown

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Top guest favorite

The exterior of a new construction home is visible, featuring a blend of wood and dark siding. A spacious porch, supported by wooden beams, invites relaxation, while tall trees surround the property, enhancing the sense of seclusion. Natural landscaping complements the tranquil setting.

Home in Jamestown

5 out of 5 average rating, 25 reviews

Onyx House

Take a break and unwind at this peaceful oasis, surrounded by nature. Minutes to Lake Cumberland State Resort Park & Marina and Halcombs Landing Boat Ramp ‘Dam’-you’ll have easy access to the water. Outdoor seating with 3 decks, outdoor tv, and fire pit allows for great social entertainment and a perfect place to unwind. 2 private bedrooms downstairs (queen), with a 4 bed (full) loft upstairs. 2 bathrooms down stairs-one with walk-in shower, one with tub/shower. The kitchen is fully equipped.

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.

A screened porch featuring a mix of red and blue chairs arranged around a table, surrounded by large windows that overlook a lush green setting. Soft lighting is provided by hanging bulbs, enhancing the inviting space.

Home in Jamestown

4.89 out of 5 average rating, 19 reviews

Jamestown - KY Lake Cottage | Boat Parking

Welcome to your seasonal getaway at Harbor Springs Cottage near beautiful Lake Cumberland! Inside, our three private bedrooms offer a haven of comfort for you and your guests, ensuring a restful night's sleep after a day of lake time. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Harbor Springs Cottage has got you covered. ☆Book your stay at Harbor Springs Cottage today and discover why life truly is better by the lake. Your perfect retreat awaits!☆

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, 19 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

4.89 out of 5 average rating, 56 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 modern tiny home is nestled among trees, featuring a light blue exterior and a striking yellow front door. Large windows allow natural light to fill the space. A red bench is positioned on the concrete patio, providing a welcoming outdoor seating option.

Home in Somerset

4.96 out of 5 average rating, 111 reviews

Cottage close to the Lake

Discover your scenery retreat in this 1-bedroom, new tiny home nestled in the woods, just 6 minutes from Lees Ford Marina. Experience the calming sounds of nature while sipping your morning coffee on the covered back porch. The fully equipped kitchen allows you to prepare your favorite meals, or you can indulge in fine dining just a short drive away. This delightful property offers the perfect blend of tranquility and convenience.

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

4.86 out of 5 average rating, 65 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

The modern mountain home is illuminated at night, highlighted by exterior lighting that accentuates its sleek design. A spacious deck invites outdoor relaxation, with a pergola and seating area visible. Large windows allow for glimpses of the interior, creating a warm ambiance against the night sky.

Home in Jamestown

5 out of 5 average rating, 55 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!

A spacious wooden deck surrounds the guesthouse, showcasing a modern architectural design with a vaulted roof. Comfortable seating and tables are arranged, complemented by potted floral arrangements. Large windows invite natural light, and the surrounding trees create a serene environment.

Home in Science Hill

4.97 out of 5 average rating, 116 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

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

A spacious living area features a high wooden ceiling with exposed beams, large windows, and a stunning stone fireplace. A large wooden dining table is surrounded by benches and chairs, while plush seating options offer comfort and relaxation. Natural light floods the room, enhancing its inviting ambiance.

Home in Burkesville

4.52 out of 5 average rating, 27 reviews

'Ledge Lodge' Burkesville Getaway: Pool & Views!

Top guest favorite

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 circular fire pit area is surrounded by five red Adirondack chairs set atop gravel. The sunny outdoor space features a neatly arranged stone perimeter, with a grassy area beyond, creating an inviting atmosphere for gatherings.

Home in Somerset

4.75 out of 5 average rating, 20 reviews

The Easy Peasy/Boat Ramp/Pool/Hot Tub/Speak Easy

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

4.82 out of 5 average rating, 22 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

A well-lit swimming pool is surrounded by lounge chairs on a concrete deck. The pool's water glows in a vibrant blue hue under the night sky, while several green umbrellas add a touch of color. The area features a secure fence and trees in the background.

Home in Burnside

4.67 out of 5 average rating, 9 reviews

Blue Lagoon at VillagerResort,Pool,Boat slip/dock

Weekly house rentals

Top guest favorite

A spacious outdoor deck features a round table surrounded by six chairs. The inviting space overlooks Lake Cumberland and is framed by tall trees, providing a serene view of the water and distant hills under a clear sky.

Home in Monticello

5 out of 5 average rating, 22 reviews

Luxury Lake Home! Dock Holidays Lake View Inn

A charming farmhouse features light grey siding and a red metal roof. The front porch is adorned with two white rocking chairs and potted plants. Large windows on the side invite natural light, and a spacious lawn surrounds the home, enhancing its serene rural setting.

Home in Greensburg

4.96 out of 5 average rating, 28 reviews

Restored 1940s Farmhouse Near Wedding Venue

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

The spacious kitchen features modern appliances, a large island with seating, and a rustic wooden ceiling that enhances the airy atmosphere. A dining area is visible with an expansive table and multiple chairs, complemented by large windows allowing natural light to fill the space.

5 out of 5 average rating, 33 reviews

Retreat at Wolf Creek

The exterior of a modern cottage is depicted, featuring gray siding and a welcoming front porch. A well-maintained lawn surrounds the driveway leading to a two-car garage. The home is set against a backdrop of trees, creating a peaceful rural ambiance.

Home in Somerset

4.92 out of 5 average rating, 25 reviews

Cumberland Cottage

A spacious barndo-style home features a covered porch with seating, set against a backdrop of lush greenery. The exterior includes large windows and a gravel driveway, providing ample parking space. The mix of white siding and dark roofing adds a modern touch to the country setting.

Home in Russell Springs

4.86 out of 5 average rating, 50 reviews

Barndo: 5 Minutes From Lake Cumberland Marina

Top guest favorite

A single-story home is displayed with a covered porch and outdoor seating area. The exterior features a mix of dark siding and light accents. A gravel driveway leads up to the entrance, surrounded by greenery and trees, creating a calm and spacious environment.

Home in Burkesville

5 out of 5 average rating, 36 reviews

Camping with the Cows near Dale Hollow Lake

A rustic cabin is presented with a welcoming brick facade, showcasing a simple covered porch with a bench. Flanking the entrance are two windows that allow natural light to enter. The surrounding area is lush with greenery and features a gravel pathway leading up to the door.

Home in Somerset

4.91 out of 5 average rating, 70 reviews

Buggs Cabin- water view & close to town and lake

Private house rentals

The outdoor entertainment area is illuminated at night, featuring bar seating and a television mounted above a bar. The fire pit is located at the center, providing warmth and ambiance, while a swing seat is visible in the background.

Home in Jamestown

4.89 out of 5 average rating, 9 reviews

Little Indian Retreat

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, 10 reviews

Linkview Getaway | Boat Parking

An aerial view captures the vicinity of the home, showcasing nearby landmarks like Jamestown Marina, located 3.5 miles away, and Lake Cumberland. Main Street is visible, surrounded by residential areas and green spaces under a bright sky.

Home in Jamestown

5 out of 5 average rating, 20 reviews

Catch and Relax on Main!

Top guest favorite

A modern farmhouse is captured on a cloudy day, featuring a combination of dark wood and stone facades. Large windows provide natural light, framed by a gently sloping green lawn. The symmetrical design highlights the welcoming entrance and overhanging roofline.

5 out of 5 average rating, 8 reviews

Mimi’s Place

Aerial view showcases the Airbnb nestled among lush greenery along the shoreline of Lake Cumberland. Expansive waters are visible, framed by rolling hills and dense forests. The property includes a spacious driveway leading to a picturesque home, emphasizing a serene natural landscape.

Home in Jamestown

4.73 out of 5 average rating, 79 reviews

Twin Creeks Retreat!

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

A classic Golden Tee 3D golf arcade game is displayed prominently, featuring a vibrant screen showcasing a golf course scene. The arcade cabinet includes buttons and a trackball for gameplay, providing an entertaining option for guests of all ages.

Home in Jamestown

5 out of 5 average rating, 6 reviews

The Getaway

Top guest favorite

A game room features a shuffleboard table with an illuminated edge, a foosball table, and a double-net basketball setup. The space is accentuated by a ceiling fan and wooden ceiling, while a cozy hanging egg chair provides a relaxing spot. Dark walls contrast with light flooring.

Home in Russell Springs

5 out of 5 average rating, 26 reviews

Ravenwood Retreat~NEW-4 KING beds-Games-Hot Tub!

Quick stats about house rentals in Jamestown

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ367 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