Holiday rentals in Jamestown

Little Cabin in the Woods

Welcome to our cozy one-bedroom cabin nestled in the heart of Russell Springs /ColumbiKentucky! This charming cabin is perfect for travelers seeking tranquility and relaxation. Surrounded by lush forests you'll enjoy the gentle breezes rustling through the trees.The cabin features a comfortable queen size bed a fully equipped kitchen and a cozy living area. Outside you can unwind on the spacious deck or stargaze at night.Book now and create unforgettable memories in Kentucky's scenic countryside

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.

Game Center~Riverfront Views~Family~Basketball

Welcome to The Buoy - Cabin 9 at Cabins on the Cumberland, your family’s new getaway tradition. (ONE UNIT IN OUR TRIPLEX) *Private boat ramp to the Cumberland River *20 Min to Lake Cumberland *Pickleball / Basketball & Playground *Game Center w/ Pool, PingPong, Arcades, Shuffleboard *Private Firepit *Barrel Saunas *Dog-friendly *Pack-n-play, high chair NOTE: This is a cabin community of 12 cabins, we do have other cabins available for your larger groups. Read important notes prior to booking.

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.

Tiny LakeView Cottage~Pets! 1 nights available

We welcome your fur babies!! Kayaks available! Ice maker! Coffee pot w/coffee & creamer! Adorable, cozy tiny house with two decks & bonfire pit overlooking Lake Cumberland! It is located in Monticello, Ky, in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. On a dead end street, so very peaceful. Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

The Cozy Cabell Cottage

It’s time for an adventure at our vacation rental, Cabell Cottage. With Lake Cumberland only 5 minutes away via the Cabell landing....really your boat is 5 minutes from being in the water; the cottage can be your base for all things fun on the lake (swimming, boating, and fishing). Did I CATCH your interest with fishing. However, if it’s a retreat you seek, the cottage is also for you as it sits in a quiet, very pretty, rural area of Wayne County, Kentucky, where 5 can sleep easily.

Studio @ 219 - close to LWU, lakes, parkway

Our studio apartment is a recently remodeled extension of our home. Rest easy and assured, knowing that we are right next door to help you in any way! We are located within 2 miles of Lindsey Wilson University, between Green River Lake and Lake Cumberland and within one mile of the Cumberland Pkwy. We are ready to welcome guests who are in town for events, visiting family, vacationing, or just passing through! We look forward to taking care of you while you’re traveling!

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 Lodge

Stylish 2BR/1BA retreat with private Cumberland River access. Sleeps 6 with open-concept living, full kitchen, and pull-out sofa. Relax on the covered front & back porches, gather around the fire pit, or fish and kayak right from the property. Nestled on a quiet dead-end road yet only 15 min to Jamestown & Jamestown Marina. Perfect for families or friends seeking comfort, style, and a peaceful getaway with the whole family at this peaceful place to stay.

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!

New near Jamestown Dock - B

Great getaway! 4 miles from Jamestown Marina and 10 mins from State Dock. This apartment has 2 bd, 1 bath, open kitchen, living room. This apartment sits inside a small warehouse up a set of stairs with a large open driveway to make for easy access in and out with your boat. Over all there is plenty of room to relax and enjoy your stay! * This apartment is on the 2nd floor so there will be some steps to climb to get to it.

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.