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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, 142 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, 174 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

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, 18 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

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

5 out of 5 average rating, 105 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 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, 8 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.

The exterior of a wooden cabin is presented, featuring a rustic design and a welcoming front porch. A combination of light and dark wood panels creates visual interest, while landscaped gravel areas enhance the entryway. Natural surroundings complement the tranquil lakeside atmosphere.

Home in Jamestown

4.85 out of 5 average rating, 26 reviews

Lily's Paradise Lake House

Wanting to plan a getaway with friends and family? Let Lily's Paradise take care of you. Our lake house is here to help you unwind and have fun. Our lake house is located minutes away from the beautiful Lake Cumberland. We are located in the center of Jamestown and only minutes away from Russell Springs and Somerset. Enjoy time at the lake only 3 miles from Lily Creek Boat Ramp, 1 mile from Pepe's Mexican Grill, 2.5 miles from Mini Indy, 0.8 miles from Dollar General Market and much more.

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

4.92 out of 5 average rating, 13 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!☆

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, 16 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 exterior of a single-story house is presented, featuring a light grey facade with a distinct address number. A driveway leads up to the entrance, flanked by manicured landscaping. The surrounding trees are in early spring foliage, and a clear blue sky is visible overhead.

Home in Jamestown

5 out of 5 average rating, 73 reviews

Marina Views, Good for Big Group-Discount Specials

****SPECIALS ENDING SOON *** Fall for Savings: Grab Your Lake Escape Now! Book your fall trip to the lake and enjoy a ***50% discount*** on your nightly rate for trips booked between 9/2/2025-11/30/2025 (blackout dates apply). This promotion will end on June 20th. Summer Weekday Special: Book your trip on any weekday and receive 25% off your nightly rate! This promotion applies to any weekday night (M-F) from June 1-August 31. This promotion will end on June 30th.

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, 128 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

4.92 out of 5 average rating, 49 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 exterior view of a house features a welcoming front porch with two comfortable seating areas. Lush green grass surrounds the property, and large trees provide shade, creating a serene outdoor space. The entrance is highlighted by a prominent front door with a lantern above.

Home in Jamestown

4.9 out of 5 average rating, 20 reviews

Cozy Lake Time Retreat

Kick back and relax in this calm, stylish space. Perfect location for visiting the lake or family. Come stay at our 3 bedroom 2 bath home that is centrally located in Jamestown for easy access to multiple docks. The home is adequately furnished with everything you would need to enjoy your time at Lake Cumberland. It sits in the 1.5 acres so there is plenty of room to gather and enjoy the outdoors. *Master bedroom upstairs has very low ceilings.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations 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 tranquil saltwater pool is surrounded by a white fence, featuring a single lounge chair and two additional chairs positioned nearby. Clear blue water reflects the sky, while green trees are visible in the background, enhancing the peaceful outdoor setting.

Home in Campbellsville

4.89 out of 5 average rating, 45 reviews

Beautiful sunrises near Green River Lake NO pets

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, 7 reviews

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

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

4.72 out of 5 average rating, 53 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

4.77 out of 5 average rating, 13 reviews

Take It Easy@The Easy Peasy

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

4.79 out of 5 average rating, 19 reviews

Burnside Bungalow, w/ dock, pool & firepit

Top guest favorite

A spacious living area features a stone fireplace and colorful wall art, with a vibrant mural depicting sunflowers. Comfortable seating is arranged around a central coffee table, and large windows allow natural light to fill the room, enhancing the welcoming atmosphere.

Home in Burnside

4.94 out of 5 average rating, 18 reviews

Gallery on the South Fork (9R) Lake, Pool, Art

A heated swimming pool is surrounded by lounge chairs and umbrellas, with a diving board extending over the water. The pool's clear blue water reflects the bright sky, while a building is visible in the background, providing access to additional amenities.

Home in Russell County

Lake Cumberland Ky State Park Q6

Top guest favorite

Home in Pulaski County

5 out of 5 average rating, 16 reviews

Lake-Front Woodson Bend 14-1

Weekly house rentals

Top guest favorite

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, 15 reviews

Fawn Run on Lake Cumberland

Top guest favorite

A one-story farmhouse is shown under a clear blue sky, featuring a light-colored exterior and a metal roof. A wide driveway leads to the carport, with well-maintained greenery surrounding the property and colorful flower beds at the base of the porch.

Home in Greensburg

5 out of 5 average rating, 21 reviews

Hillview Haven

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, 91 reviews

The ranch house. Relax and unwind

A modern floating home is depicted on tranquil waters, featuring large windows and a spacious deck. Comfortable outdoor seating is arranged near a fire pit on a well-maintained surface. Surrounding greenery is visible, enhancing the peaceful lakefront setting.

Home in Russell Springs

5 out of 5 average rating, 3 reviews

On-Water 20

Top guest favorite

The image displays a cozy living area featuring a comfortable brown sofa and a glass coffee table, with large windows that provide natural light. A view of Lake Cumberland is visible through the window, showcasing the calm water and rocky shoreline.

5 out of 5 average rating, 15 reviews

Lake cottage; 6m walk (1,100f to water); Nancy, KY

Top guest favorite

The exterior of the Riverside Retreat features a charming two-story home with a gabled roof and a welcoming entrance. A stone pathway leads to the front door, framed by subtly lit landscaping and blooming flowers. Lush greenery is visible in the background, enhancing the tranquil setting.

Home in Peytonsburg

5 out of 5 average rating, 16 reviews

Riverside Retreat

Top guest favorite

The exterior of Foster Lodge is showcased, featuring a charming brick facade under a partly cloudy sky. Surrounding landscaping includes manicured grass and several trees, with autumn leaves providing a seasonal touch. A walkway leads to the front entrance, enhancing the inviting appearance of the home.

Home in Campbellsville

5 out of 5 average rating, 65 reviews

Foster Lodge at Green River Lake - Pet Friendly

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

4.93 out of 5 average rating, 46 reviews

NEW Barndo: 5 Minutes From Lake Cumberland Marina

Private 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, 16 reviews

Luxury Lake Home! Dock Holidays Lake View Inn

A charming farmhouse is surrounded by lush greenery, with a spacious front yard. The entrance features two wooden doors flanked by hanging flower pots, leading to a covered porch adorned with blue seating. A concrete pathway guides visitors to the entrance.

4.92 out of 5 average rating, 13 reviews

Elisi's Cozy Nook 3.2 mile from Marina Rowena.

Top guest favorite

A single-story brick home is framed by lush greenery, featuring a dark exterior with a welcoming front porch and a circular window. A spacious driveway leads to an attached garage, while the surrounding lawn is neatly maintained, providing ample outdoor space.

Home in Columbia

5 out of 5 average rating, 12 reviews

Dale's Place

Top guest favorite

A cozy living area features floral patterned sofas arranged around a white coffee table. Ceiling fans provide ventilation, while nautical decor, including crossed oars, adorns the walls. Natural light fills the space from nearby windows, with a view leading into the kitchen area.

Home in Russell Springs

4.97 out of 5 average rating, 29 reviews

Lake Top Cabin #10

Top guest favorite

Home in Somerset

4.98 out of 5 average rating, 93 reviews

New Lakefront Luxury: Hot Tub, Arcade,Serene Views

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

4.93 out of 5 average rating, 46 reviews

Abells Spring Branch

A modern two-story home is nestled among trees, featuring a spacious outdoor deck. The structure showcases large glass windows, allowing natural light to fill the interior. A golf pad is visible in the foreground, set against a backdrop of a vibrant sunset sky.

Home in Burnside

4.95 out of 5 average rating, 39 reviews

Lake Cumberland Luxury! Lake views, golf, hot tub

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

4.9 out of 5 average rating, 62 reviews

Buggs Cabin- water view & close to town and lake

Quick stats about house rentals in Jamestown

Total rentals
20 properties
Nightly prices starting at
G$20,915 GYD before taxes and fees
Total number of reviews
440 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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