Family-friendly holiday rentals in Jamestown

Garage Door to the Wilderness!

Welcome to this stylish and sleek tiny home that's perfect for modern living! With ample space to sleep 4, features a bathroom complete with a beautifully tiled custom shower. The kitchen is a chef’s delight, black cabinetry and elegant granite counters.Enjoy the seamless flow of heated tile flooring throughout, leading you to the covered back porch where you can sip your morning coffee! The back garage door offers easy access to nature’s beauty. Located 5 minutes from either town or the lake!

Riverfront~Firepit~Fishing~20 Min Lake Cumberland

Welcome to The Anchor (Cabin 7) at Cabins on the Cumberland, your family’s new tradition. *Private boat ramp to access the Cumberland River *Pickleball/Basketball Court & Playground *Sleeps 6, this is ONE unit of our TRIPLEX *20 min drive to Halcomb’s Landing - access to Lake Cumberland *Firepit *2 min Creelsboro Country Store *Pack-n-play and high chair NOTE: This is a cabin community, we do have other cabins available for your larger groups. Read our important notes below prior to booking.

Country stay near the Falls-Polar Express Railway

Welcome to our countryside getaway nestled on almost 5 acres within 5-20 miles of Burnside, Lee's Ford, and Conley Bottom Marinas. Enjoy the day on Lake Cumberland. Come back to relax, eat, drink & be merry. Gather around the outside barbecue area and fire pit or snuggle up inside next to the fireplace, playing games or watching a movie. Whether you are on a couple's retreat, fishing buddy's getaway, or family vacation - the house and outdoor area provide plenty of room to relax and enjoy.

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.

Home by Wolf Creek Marina & Boat Ramp Pets Welcome

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.

Dixie Mtn. Hideout

Enjoy a breath taking Mountain view from your private log cabin as you drink your morning coffee. With memory foam beds you will wake refreshed and ready to enjoy all the Lake Cumberland area has to offer. Within 5 miles to General Burnside Sate Park and boat ramp and Burnside Marina. Your vacation home is only 10 miles from downtown Somerset, somernites car cruise capital! Boat parking available with turn around. Dixie Mtn. Hideout, when you're away from home, we welcome you home!

Page's Legacy: Favorite Fall Getaway

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"

Studio @ 219 - close to LWU, lakes, parkway

Our studio apartment is a recently remodeled extension of our home. Rest easy and assured, knowing that we are right next door to help you in any way! We are located within 2 miles of Lindsey Wilson University, between Green River Lake and Lake Cumberland and within one mile of the Cumberland Pkwy. We are ready to welcome guests who are in town for events, visiting family, vacationing, or just passing through! We look forward to taking care of you while you’re traveling!

Small cabin close to town

Cabin was built by my grandparents about 40 years ago using timber cut from the land. Cabin is about 5 miles from town but feels country. Road is quite, with just local traffic, local being the people that live on the road. Very quite setting. Great place to relax where ever you find yourself, wither it is in the house, on one of the porches, or in the yard. House also has a fire pit in the back yard, & a charcoal gill if you want to grill out. We are pet friendly!

Crow's Nest (A.K.A. Roughing It) at Foggy Bottom

Crow's Nest, A.K.A. Roughing it, is a small one room cabin located in a wooded area by a running stream. There is no bathroom (you will have access to campground bathhouse), there is twin bunkbed, as well as a fold out chair bed, and a small kitchen area with limited kitchen amenities. It is a very private place where you can sit on the front porch, listen to the creek and possibly see the local wild life.