Holiday rentals with a patio in Jamestown

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.

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 Boat Haus Guesthouse

A rustic barn-do-minium on the Cumberland River. Come enjoy this relaxing space with friends, family or fishing enthusiasts. Located on the Cumberland River, known for its beautiful views and plentiful trout fishing and only 14 miles from Lake Cumberland’s Halcomb boat ramp. As a renter, you have access to our private community river boat ramp adjacent to the guesthouse. Perfect for a smaller group of fishing enthusiasts or family of 4. For larger group search Airbnb for "Trout Haus"

Hidden Creek Schoolhouse

Not all escapes are found on maps; some are found in time. Tucked into a quiet hollow between Dale Hollow Lake and Lake Cumberland sits a 1919 schoolhouse where stories linger and life slows. Original wood floors whisper history, the seasonal creek hums when it pleases, and the skies put on a show in every season. Wander to the lakes or stay wrapped in the stillness…spring blooms, autumn glows, winter hushes. Hidden Creek is a storybook stay you step into, not rush through. Book early!

Timberview Cottage

Welcome to your perfect getaway! This brand-new, 2 bedroom, 1 bath cottage offers the ideal blend of comfort, privacy, and fun. Nestled on a peaceful, wooded 2-acre lot, you'll enjoy a serene country setting with all the conveniences of being just minutes from town and multiple Lake Cumberland marinas. Whether you're here to boat, explore, or simply unwind, this cottage makes the perfect home base. Relax in the hot tub under the stars or head out and be lake-side in no time.

Bluegrass Fables @ Beaver Creek

At Bluegrass Fables, your story begins with breathtaking vistas of Lake Cumberland. Perched on a mountain above Beaver Creek's confluence with the main channel, this luxury retreat offers a modern lodge aesthetic and a million-dollar view. Immerse yourself in nature’s beauty, luxury finishes, and a setting that feels like the start of an unforgettable tale. Whether for friendship, family, or solitude, this is more than just a getaway; it’s the next chapter of your story.

Weekend at Bernie's Cabin at Lake Cumberland KY

Cozy, Renovated A Frame Cabin. Updated kitchen with large island and eat in area. Updated bathroom. One bedroom downstairs with queen bed. Loft upstairs with two additional queen beds. 2 smart TVs. WiFi better than you can find in the city. Perfect getaway close to Lake Cumberland, Lily Creek Ramp or Jamestown Marina. Room to park a small boat. Large wrap around porch and fire pit make for perfect outdoor space. Come enjoy our home away from home! Absolutely no pets.

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.

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!

Lake Escapes on the Square

The whole group will be comfortable in this spacious and unique space located right on the square in Jamestown. Bedroom 1 - Queen Bed Bedroom 2 - Full Bed Located 3.5 miles from Jamestown Marina, 12 miles to Wolf Creek Dam, 13 miles to State Dock, 0.8 miles to Dollar General Market, walking distance to Reel Java, Giovanni’s Pizza & Snap’s Soda Shop! 2 parking space maximum NO ROOM FOR BOATS OR TRAILERS This apartment is located upstairs!

Welcome to your Dream Lake Home

Welcome to a place to forget your cares. This stylish home is perfect for family or group trips. Stunning lake views year round, 5 bedrooms/3 baths, games for kids or adults including foosball and ping-pong, a grilling area and full kitchen to prepare your catch of the day, a cozy electric fireplace, and a boat ramp less than 1 mile for easy access to all your water activites. Come see why they say "Lake life is the best life!"

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.