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.

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!☆

HOT TUB~Fishing BoatRamp~LakeCumberland~RiverCabin

Welcome to The Campsite (Cabin 4) at Cabins on the Cumberland, family traditions start here. *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, we do have other cabins available for your larger groups. Read our important notes below prior to booking.

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.

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.

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!

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.

Turkey's Roost at Foggy Bottom

Located close to the Cumberland River, Lake Cumberland and Wolf Creek Dam, this cozy cabin is perfect for solo adventurers, couples in need of a quiet retreat, or small families looking for some outdoor fun - both human children and pet children welcome! The hill to this property is very steep, and there is no turn around for a boat. Just let us know if you are bringing a boat, and we will let you know where you can park it.

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.

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

Lake Cumberland State Park Villa

Fish, hike, swim in the heated pool, play putt putt golf, enjoy archery courses, horseback riding, play basketball, tennis or pickleball all while nestled in the Apple Valley Resort! Your 2 Bedroom, 2 Bath Townhome awaits! There is also a Gazebo with several picnic tables, grills, a playground, a boat shed and more!!! We look forward to hosting you, your friends & family!! Pool is closed for season.