Family-friendly holiday 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.

Comfort · Location · Quiet

Kentucky Coal Cabin 2 min from Lake Cumberland

Come explore the Lake Cumberland area in style with a fully stocked cabin, everything you will need for a great stay!! A home away from home!! 5 beds, a fully stocked kitchen, beautiful front porch/deck with rocking chairs to enjoy all the summer nights, a huge firepit and a fireplace inside!! Hike, fish and explore your way through Wolf Creek Dam and all the amenities it has to offer including a National Fish Hatchery, play area, splash pad, great food and boat ramps. The State Dock is 2 min!!

Indoor spaces · Family · Parking

The Bourbon House - No Cleaning Fees

Take it easy at this unique Kentucky Bourbon themed getaway only 10 minutes away from Lake Cumberland via the Jamestown Marina with No Cleaning Fees. 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.

Indoor spaces · Kitchen · Decor

Tiny LakeView Cottage~Pets~Best Sunset~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.

Kitchen · Family · Air conditioning

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!☆

Kitchen · Family · Walkability

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.

Family · Indoor spaces · View

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.

Kitchen · Value · Sleep quality

Modern Home near Lake Cumberland/Hot tub/Fire pit

Welcome to your perfect getaway! This modern, 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.

Indoor spaces · Family · Nearby

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!

Kitchen · Family · Access

Lake Daze Blue Cottage <1 Mile to Jamestown Marina

Cozy 2 Bedroom Cottage located minutes from Jamestown Marina and Beautiful Lake Cumberland. Spacious house exhibits 2 large bedrooms and 1 full bath. Ample room to sleep 8 comfortably. Scenic wooded views, property is surrounded by woods but with a short walk on the path through the woods you can walk through Timber Point resort to grab a bite or coffee at the Reel Java cafe. Ample parking for boats and vehicles with two entrances.

Kitchen · Family · Parking

Weekend at Bernie's Cabin at Lake Cumberland KY

Cozy A-frame with the rustic-but-comfortable balance just right. Queen bed and bath downstairs, two more queens in the loft, sleeps 6. Big kitchen island, gas grill (no charcoal), drip coffee, WiFi that beats the city. Wraparound porch, fire pit, and deer that wander through daily. Minutes from Jamestown Marina, room to park a boat on site. Self check-in smart lock. No dishwasher, no pets. Slow mornings, fast boat launches.

Kitchen · Indoor spaces · Value

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.

Family · Kitchen · Comfort