Family-friendly vacation 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 favorite
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 favorite
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 favorite
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
4.85 out of 5 average rating, 103 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!

Guest favorite
A screened porch featuring a mix of red and blue chairs arranged around a table, surrounded by large windows that overlook a lush green setting. Soft lighting is provided by hanging bulbs, enhancing the inviting space.
Home in Jamestown
4.88 out of 5 average rating, 25 reviews

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!☆

Superhost
Cabin in Jamestown
5 out of 5 average rating, 3 reviews

Bee Hive Cabin at Lake Cumberland KY

Step into this bright and open, cozy cabin retreat. With 3 comfy queen beds, you’ll have plenty of space to unwind. Out back, the cabin borders peaceful woods where deer often wander by. Gather around the cozy fire pit under the stars, fire up the grill for a cookout, and make memories that last. Less than 2 miles from Jamestown Marina and Lily Creek boat ramps, 15 miles to Wolf Creek Dam. Whether you’re here to fish, boat, hike, or simply relax, The Bee Hive is the perfect home base.

Top guest favorite
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 favorite
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 favorite
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 favorite
A spacious entryway features a striking artwork installation on the black wall, complemented by a spiral staircase leading to the upper level. Comfortable seating includes a tufted leather chair and a plush sofa, with a round wooden coffee table at the center on a decorative area rug.
Guesthouse in Somerset
4.98 out of 5 average rating, 215 reviews

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

Top guest favorite
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.

Top guest favorite
A modern chalet exterior features a striking combination of wood and metal, showcasing large windows that invite natural light. A small deck extends from the upper level, set against a backdrop of lush greenery. The entrance is marked by a concrete pathway leading to the main door.
Home in Somerset
4.91 out of 5 average rating, 169 reviews

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

Popular amenities for Jamestown family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Jamestown

  • Total vacation rentals

    Explore 20 vacation rentals in Jamestown

  • Nightly prices starting at

    Jamestown vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

  • Verified guest reviews

    Over 990 verified reviews to help you choose

  • Wi-Fi availability

    20 of Jamestown vacation 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!