House vacation rentals in Jamestown

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Top-rated house rentals in Jamestown

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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, 176 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, 22 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.

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.

Guest favorite

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.

Guest favorite

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

4.88 out of 5 average rating, 16 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!☆

Superhost

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, 149 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

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, 17 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 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.

Home in Albany

4.94 out of 5 average rating, 129 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.

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

4.89 out of 5 average rating, 54 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 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

4.88 out of 5 average rating, 24 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.

Guest favorite

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, 77 reviews

Lake View Home-Good for Big Group-Jamestown Marina

This house has one of the most amazing views! Looking right over Jamestown and State Dock Marinas, you have a perfect morning view for coffee and can overhear the marina festivities over cocktails in the evening! Only about 7 minutes (2.6 miles) to Jamestown Marina! The most loved part of our home is the back porch and the view. We always say we bought it for the view and you will know why!! Pictures don’t do it justice.

Top guest favorite

A newly renovated ranch-style home is presented, featuring a light-colored exterior and a welcoming front porch. Lush green grass surrounds the property, and a spacious driveway accommodates vehicles. Trees line the background, adding to the serene setting.

Home in Russell Springs

4.98 out of 5 average rating, 54 reviews

The Hubb

Nice, newly renovated 4 bedroom, 2 bath house with lots of room for entertainment. Large kitchen/dining room with room for 12+. Perfect house for indoor and outdoor living. In town and just a short driving distance to either Jamestown Marina or Lake Cumberland Marina. Nice 30’ driveway with a place to charge your boat. New for 2023 we now have a fire pit and new outdoor furniture for more indoor/outdoor living space!