House vacation rentals in Jamestown

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Top-rated house rentals in Jamestown

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
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, 158 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.

Top guest favorite
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, 188 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 favorite
A well-maintained cabin is set amidst a lush green landscape, featuring a sloped metal roof and a spacious front porch with steps leading to the entrance. A gravel driveway curves in front of the home, providing access to the property surrounded by trees.
Home in Albany
5 out of 5 average rating, 12 reviews

Hooked on the Lake - 6 miles from Marina Rowena

Your perfect getaway adventure awaits! Just 6 miles from Marina@Rowena, our cozy retreat is ideally located near a beautiful lake for boating, fishing and relaxing on the water. After a day of adventure, unwind in a comfortable space with a fully equipped kitchen. With ample parking for your trailer and easy access to nature, our home is the perfect base for your next outdoor escape. Please note: The lake is a short drive, not within walking distance as listed by Airbnb’s default map features.

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, 144 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 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
4.98 out of 5 average rating, 107 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.

Superhost
The historic farmhouse, set in a peaceful country setting, features a welcoming front porch with rocking chairs. Lush greenery and hydrangeas frame the entrance, while the steps lead to the door beneath a gabled roof. Sunlight highlights the well-maintained exterior.
Home in Russell Springs
4.77 out of 5 average rating, 153 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.

Guest favorite
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!

Top guest favorite
Home in Jamestown
5 out of 5 average rating, 70 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.

Guest favorite
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
4.9 out of 5 average rating, 119 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 favorite
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.

Guest favorite
A newly remodeled house with a dark exterior is situated on a lush green lawn, surrounded by trees. The structure features a unique roofline and several windows that offer natural light, creating a connection with the outdoor scenery.
Home in Jamestown
4.96 out of 5 average rating, 45 reviews

4 bed 2 bath by Jamestown Marina

Welcome to Cocktail Cove! This 4 bedroom 2 bath house has been newly remodeled and we are excited to share it with you! You couldn’t ask for a better location when visiting Lake Cumberland! Located in Jamestown, KY, we are only 2 miles from Jamestown Marina, 2 miles from Lily Creek boat ramp, and just 5 miles from the town of Russell Springs. Literally everything you need is just minutes away!

Popular amenities for Jamestown house rentals

When is the best time to visit Jamestown?

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Avg. priceﺩ.ﺇ551ﺩ.ﺇ551ﺩ.ﺇ555ﺩ.ﺇ569ﺩ.ﺇ643ﺩ.ﺇ661ﺩ.ﺇ679ﺩ.ﺇ657ﺩ.ﺇ602ﺩ.ﺇ621ﺩ.ﺇ643ﺩ.ﺇ595
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Quick stats about house rentals in Jamestown

  • Total vacation rentals

    Explore 20 vacation rentals in Jamestown

  • Nightly prices starting at

    Jamestown vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

  • Verified guest reviews

    Over 590 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Jamestown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Jamestown rentals

  • 4.9 Average rating

    Jamestown stays are highly rated by guests—averaging 4.9 out of 5!

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