House holiday rentals in Jamestown

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Top-rated house rentals in Jamestown

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Top Guest favourite
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, 189 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.

Guest favourite
A comfortable living area features a brown sofa and a light gray armchair, positioned around an area rug. Nautical-themed decor is visible on the walls, including a ship's wheel and an anchor. Natural light filters through curtains, illuminating the space.
Home in Russell Springs
5 out of 5 average rating, 7 reviews

Eagle's Nest Lake Retreat

Your family will be close to everything when you stay at this centrally-located vacation home. Our newly renovated retreat is sitting less than 8 miles from the water nestled right at the heart of Lake Cumberland. Our home is fully equipped for your family and friends. We have a large driveway and there is plenty of room to park your boat, personal watercraft or trailer if you choose to dock your boat for the weekend. Our home is located just next door to the well-known Eagle's Nest RV Park.

Top Guest favourite
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, 147 reviews

Countryside stay near Cumberland Falls-SF Railway

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 favourite
The front porch features a spacious lounge chair and a classic rocking chair, inviting relaxation at sunset. Soft lighting illuminates the area, highlighting the details of the white columns and the warm tones of the evening sky visible in the background.
Home in Russell Springs
5 out of 5 average rating, 116 reviews

Gran's Place

This newly renovated 4th generation family farmhouse sitting on 13 acres is centrally located in Russell Springs, just minutes from Lake Cumberland. We are just off the Cumberland Parkway (a short and easy drive to both Columbia and Somerset), close to Russell County Hospital, and within a mile to most fast-food chains, restaurants, gas, and grocery. Our goal is to make your stay as enjoyable as possible while visiting the Lake Cumberland area. We do ask that there be no smoking in the home.

Guest favourite
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
4.97 out of 5 average rating, 108 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.

Top Guest favourite
A spacious outdoor seating area features a comfortable sectional sofa with soft cushions and accent pillows. A coffee table, adorned with a potted plant, is positioned in front. Beyond, a firepit with multiple chairs invites relaxed gatherings, set against a backdrop of lush trees.
Home in Monticello
4.99 out of 5 average rating, 100 reviews

Lake Access, SPA, FirePit, KING En-suites

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 1.2 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

Top Guest favourite
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.

Guest favourite
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, 61 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!

Superhost
A hot tub is situated on a wooden deck beneath a pergola adorned with string lights. Soft blue water glows, reflecting the warm ambiance. A dining set with light-colored chairs is visible in the background, creating a relaxed outdoor space.
Home in Russell Springs
4.8 out of 5 average rating, 245 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 favourite
Home in Jamestown
5 out of 5 average rating, 73 reviews

Modern Mountain Retreat | Fireplace & Luxe Design

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.

Top Guest favourite
A modern chalet exterior features a striking combination of wood and metal, showcasing large windows that invite natural light. A small deck extends from the upper level, set against a backdrop of lush greenery. The entrance is marked by a concrete pathway leading to the main door.
Home in Somerset
4.91 out of 5 average rating, 127 reviews

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

Top Guest favourite
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, 119 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.

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