Family-friendly vacation rentals in Jamestown

The Lake Nest Off Jamestown Square - Hot Tub!

Enjoy the HOT TUB at The Lake Nest! - Walking distance of town square to restaurants via sidewalk close by - Approx. 4 miles to Jamestown Marina - 3 miles to Lily Creek Boat Ramp Beautiful neighborhood in town & close to lake - 2 bedroom with 3 beds (1 King, 1 Queen & 1 Queen Sleeper Sofa) - 1 full bath - Fully equipped kitchen - Hot tub - Plenty of parking & more! No parties, no smoking, no pets, etc. Note: 1 security camera on the front porch for security purposes only. No other cameras.

Tiny LakeView Cottage~Pets Welcome! Kayaks!

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.

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!☆

HotTub~Riverfront~Firepit~PingPong~Lake Cumberland

Welcome to The Woodlands (Cabin 5) at Cabins on the Cumberland, your family’s new getaway tradition. *Private boat ramp to the Cumberland River *20 Min to Lake Cumberland *Pickleball / Basketball & Playground *NEW hot tub *Game Center w/ Pool, PingPong, Arcades, Shuffleboard *Private Firepit *Barrel Saunas *Dog-friendly *Pack-n-play & high chair NOTE: This is a cabin community and we do have other cabins available for larger groups. Read our important notes below prior to booking.

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.

The Stable @ Bluegrass Gables

Enjoy some retro vibes in this converted barn. Indulge your senses, from the smell of the pine shiplap to the sounds of the wind chimes on the breezy covered porch or some vintage vinyl on the victrola turntable. Light a fire and watch the flames dance in the wood burning stove. Enjoy sips of your favorite beverage from a rocking chair with a view of the Appalachian foothills. Soak in the hot tub! Vintage china, glassware, art, vinyl, furniture, games, it's all in the details.

Charming A-frame with Lake Cumberland Views

Step back in time and unwind at this charming A-frame lakeside house, where stunning lake views and a groovy 70s vibe await! Nestled right by the water overlooking Jamestown Marina, just a few miles from the boat ramp. This mid-century gem is the perfect blend of nostalgic style and modern comfort. Whether you're relaxing on the deck, watching the sun set over the water, or curled up inside with a good book, you’ll feel the peace and nostalgia that this retro paradise offers.

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

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.

Crow's Nest (A.K.A. Roughing It) at Foggy Bottom

Crow's Nest, A.K.A. Roughing it, is a small one room cabin located in a wooded area by a running stream. There is no bathroom (you will have access to campground bathhouse), there is twin bunkbed, as well as a fold out chair bed, and a small kitchen area with limited kitchen amenities. It is a very private place where you can sit on the front porch, listen to the creek and possibly see the local wild life.

The Dock House

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.

Romantic Retreat | Fireplaces, Fire Pits & Views

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.