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.

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Top guest favourite
The exterior of a new construction home is visible, featuring a blend of wood and dark siding. A spacious porch, supported by wooden beams, invites relaxation, while tall trees surround the property, enhancing the sense of seclusion. Natural landscaping complements the tranquil setting.
Home in Jamestown
5 out of 5 average rating, 35 reviews

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.

Top guest favourite
The front porch features a spacious lounge chair and a classic rocking chair, inviting relaxation at sunset. Soft lighting illuminates the area, highlighting the details of the white columns and the warm tones of the evening sky visible in the background.
Home in Russell Springs
5 out of 5 average rating, 117 reviews

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.

Guest favourite
A tiny home is depicted with a metal exterior and a sloped roof. A front porch area features several chairs in various colors arranged on gravel, providing a welcoming space for guests. A single white door and a nearby window are also visible.
Tiny home in Nancy
4.86 out of 5 average rating, 104 reviews

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!

Top guest favourite
Home in Monticello
4.99 out of 5 average rating, 109 reviews

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 1.2 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

Top guest favourite
Cottage in Monticello
5 out of 5 average rating, 109 reviews

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.

Guest favourite
Home in Jamestown
5 out of 5 average rating, 6 reviews

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.

Superhost
The exterior of the cabin showcases a distinct A-frame design, featuring wooden siding and a blue front door. Surrounding greenery adds a natural touch, while a wooden walkway leads to the entrance. The setting is tranquil, framed by bare trees.
Cabin in Russell Springs
4.83 out of 5 average rating, 111 reviews

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!

Top guest favourite
Home in Jamestown
5 out of 5 average rating, 83 reviews

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.

Guest favourite
Cottage in Nancy
4.89 out of 5 average rating, 106 reviews

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.

Guest favourite
An open kitchen and dining area is displayed, featuring a dining table with six chairs. The kitchen includes a range, coffee maker, and shelves with dishware. Adjacent to the area, a comfortable seating arrangement and a television are positioned, surrounded by wood-look flooring and soft wall colors.
Flat in Jamestown
4.98 out of 5 average rating, 52 reviews

New near Jamestown Dock - A

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 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!

Top guest favourite
A rustic log cabin with a stone chimney is surrounded by lush greenery. The front porch features a wooden railing and an American flag hanging prominently. Steps lead to the entrance, showcasing the cabin's historical craftsmanship and natural setting.
Home in Wayne County
4.99 out of 5 average rating, 146 reviews

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.

Top guest favourite
Home in Jamestown
5 out of 5 average rating, 19 reviews

Linkview Getaway | Boat Parking

Newly remodeled, spacious, comfortable and relaxing. Plenty of parking for several vehicles, boats and trailers. Hope you choose us for your next Lake Cumberland stay.

Popular amenities for Jamestown family-friendly rentals

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 £59 per night before taxes and fees

  • Verified guest reviews

    Over 990 verified reviews to help you choose

  • Wifi availability

    20 of Jamestown holiday rentals include wifi 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!