
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 Dream Lake House
Looking for an enchanted get away close to the lake? Look no further. Only 5 minutes to Lake Cumberland and 5 minutes to Somerset, This TS decorated tiny is your dream come true! Walk into a Swifty's dream, with welcoming friendship bracelets! Tiny house is equipped with full size kitchen and full bathroom! Queen size luxury mattress and a pull-out sofa makes this big enough for the whole family! You will find a towel warmer, stocked coffee bar, w/d, grill and much more! This s a must see!!!

Tiny LakeView Cottage~Pets! 1 nights available
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.

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!

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.

Page's Legacy: Spring Getaway at the Lake
All rooms have a view of the lake and the deck overlooks Dale Hollow. We are a mile from Wolf River Boat Dock. The suite is downstairs with a private entrance. There are walking paths that encompasses 3 acres on the property. The private deck has a fire pit for chilly mornings to enjoy coffee or relaxing evening. There are some great day trips I have added to the "Host Guidebook" Click on "More about this location" and scroll to the bottom and click on "Show Host Guidebook"

The Little FarmHouse
Historic farmhouse in a peaceful country setting. Home was built by World war 2 veteran! Kitchen has all your basic needs ;Crock pot, Coffee maker and toaster , washer and dryer for your convenience! The bathroom and one bedroom is on main floor and upstairs are 2 more bedrooms plus a tiny sunroom with a daybed and a trundle bed that’s great for kids. Lovely front porch where wildlife can often be seen! Convenient location with driveway right off of HWY 80 and 5 miles from town

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.

Beautiful Cabin 4 mins from Cumberland Lake
Kick back and relax in this stylish 1-bedroom cabin with a loft that includes 2 twin beds and a queen pull-out sleeper sofa. A fully stocked kitchen, beautiful front porch/deck with rocking chairs, a swing, and a fire pit to enjoy the beautiful nights. The State Dock, Wolf Creek Dam, and Cumberland River are just 4 minutes away! Make sure to explore Wolf Creek Dam and all the amenities it has to offer!

Studio Cottage on the Square
The Cottage on Town Square is centrally located to everything you'll need on your stay in Jamestown. The cottage is located just 3 miles from the Safeharbor Jamestown Marina. The layout of our "cottage" is a studio master (King Bed) with a separate bunk room (top and bottom twins) and full bath. You will have you're own private parking in the back and there's plenty of room for your boat as well.
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

Private Luxury Dome • Hot Tub • Dale Hollow Lake

Retreat: Hot Tub & Huge Deck!

Sleeps 12 · Lakeview · Arcade · Hot Tub

4BR at Lake Cumberland - Hot Tub, Near Boat Ramps

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

HotTub~Riverfront~Firepit~PingPong~Lake Cumberland
Family- and pet-friendly home rentals

Hilltop Haven

Kentucky Coal Cabin 2 min from Lake Cumberland

Lake House "Dar Bida" Monticello

Plush Yome Tucked in the Woods

Lake Cumberland Marina - The Blue Alligator

Peaceful Stay near Falls, Conley Bottom & Burnside

Lake Daze Blue Cottage <1 Mile to Jamestown Marina

The Caelestis Yurt
Family-friendly home rentals with a pool

Lake Cumberland State Park Villa

Joplin at Villager Resort-Pool,Boat slip/dock

Lakeside Hideaway I - lakefront w/hot tub

White Oak Cottage - Resort Pool, Boat Slip

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
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 $136 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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