
Family-friendly holiday rentals in Jamestown
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Top-rated family-friendly rentals in Jamestown
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Onyx House
Take a break and unwind at this peaceful oasis, surrounded by nature. Minutes to Lake Cumberland State Resort Park & Marina and Halcombs Landing Boat Ramp ‘Dam’-you’ll have easy access to the water. Outdoor seating with 3 decks, outdoor tv, and fire pit allows for great social entertainment and a perfect place to unwind. 2 private bedrooms downstairs (queen), with a 4 bed (full) loft upstairs. 2 bathrooms down stairs-one with walk-in shower, one with tub/shower. The kitchen is fully equipped.

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.

The ranch house. Relax and unwind
Quiet, peaceful, country setting. There are country roads for walking and bike riding. For the boaters and fishermen, we are just minutes away from Arnold’s landing boat ramp and also Holmes Bend marina on beautiful Green River lake. For the hunting enthusiast, there are 20,000 plus acres of public land available for spring and fall hunting, with an abundance of turkey and deer. Close to Campbellsville University and Lindsey Wilson in Columbia. Lake Cumberland is also a short drive away.

Jabez Gem by Wolf Creek & boat ramps, pet friendly
Tiny home near Lake Cumberland, Wolf Creek Marina (4.5 miles) Dudley boat ramp (1.2 miles). Beach Grove boat ramp (1.5 miles) Harris grocery (3 miles) Mill spring battle field visitors center is close by (15 miles) 30 minute drive to the Somerset, which has breweries & restaurants. Opening soon Horse Soldier bourbon!! Hour drive to Cumberland falls park. It has a bedroom, kitchen and full shower. Bring your boat and your furry friends to our peaceful tiny home. We hope to see you soon!

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.

Da Bears Den Lakeside Retreat
Nestled just above Lake Cumberland Marina (Alligator II) There’s room for everyone at this modern and rustic Lake Cabin. Our large Deck is perfect for your next retreat. This property features a King Master Bedroom, Full Bunk Room for the Kiddos, and Double Queen Beds in our spacious loft. The Kitchen is fully stocked with all the essentials and this Cabin also has Laundry Center. Linens are included. WiFi Internet and Flat Screen TV's throughout. PETS WELCOME!

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.

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.

8-Acre Escape: Fishing Pond, Waterfalls, Disc Golf
Escape to our peaceful Kentucky lake house on an 8-acre private retreat on Lake Cumberland. Perfect for families and nature lovers, this pet-friendly home offers stunning views, a private pond, waterfalls, and a cozy fireplace. Enjoy modern amenities like Starlink internet and a fully equipped kitchen. A year-round destination for relaxation and adventure.

Nancy Kentucky - The Faubush Cabin
Log cabin from the 1800s that was moved to this location from Jackson County Kentucky complete with original stone fireplace. Located near multiple boat ramps and marinas on Lake Cumberland. Quiet setting with lots of wildlife just outside of Nancy Kentucky.
Popular amenities for Jamestown family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Lakehouse with a View

1/2 mile from Lake Cumberland Marina & NEW HOT TUB

Retreat: Hot Tub & Huge Deck!

Sleeps 12 · Lakeview · Arcade · Hot Tub

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

The Farmhouse at Brainard Valley Ranch

The Enchanted Hideaway /Pet Friendly with Hot Tub!

23 Acre Lake Cumberland: Boats & Fishing Oasis
Family- and pet-friendly home rentals

Kentucky Coal Cabin 2 min from Lake Cumberland

Little Cabin in the Woods

Horse & Buggy Country Inn

Ina's Place

HillTop Hideaway #9

Lake House "Dar Bida" Monticello

Dixie Mtn. Hideout

Lake Cumberland Marina - The Blue Alligator
Family-friendly home rentals with a pool

Gated Golf Course Condo w/view of Lake Cumberland

4 bedroom, private pool 8 person hot tub

Cozy Cabin w/Hot Tub in Lake Cumberland Resort, KY

Burnside Bungalow, w/ dock, pool & firepit

Whispering Woods Cottage | Hot Tub | Pool

Lake-Front Woodson Bend 14-1

Gidget at Villager Resort-Pool,Boat slip/dock

Woodson Bend Resort Golf/Pool/Pickleball and More!
Quick stats about holiday rentals that are family-friendly in Jamestown

Total holiday rentals
Explore 20 holiday rentals in Jamestown

Nightly prices starting at
Jamestown holiday rentals start at $135 NZD per night before taxes and fees

Verified guest reviews
Over 990 verified reviews to help you choose

Wi-Fi availability
20 of Jamestown holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Jamestown rentals

4.9 Average rating
Jamestown stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Russell County
- Family-friendly rentals Kentucky
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