Family-friendly holiday rentals in Jamestown

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.

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 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.

Weekend at Bernie's Cabin at Lake Cumberland KY

Cozy, Renovated A Frame Cabin. Updated kitchen with large island and eat in area. Updated bathroom. One bedroom downstairs with queen bed. Loft upstairs with two additional queen beds. 2 smart TVs. WiFi better than you can find in the city. Perfect getaway close to Lake Cumberland, Lily Creek Ramp or Jamestown Marina. Room to park a small boat. Large wrap around porch and fire pit make for perfect outdoor space. Come enjoy our home away from home! Absolutely no pets.

The Bourbon House

Take it easy at this unique Kentucky Bourbon themed getaway only 10 minutes away from Lake Cumberland via the Jamestown Marina. The Bourbon House has two queen beds in their own bedrooms and a full sized pull out sofa with 2 full bathrooms. It has a fully equipped kitchen but is only 5 minutes away from Jamestown Square with 3 different delicious restaurant options. Enjoy the peace of being in the country on the back patio facing the woods, with a fire in the fire pit.

Lake Life Dot Calm (Slip Available)

Welcome to your new peaceful retreat less than 2 miles from Jamestown Marina and Lilly Creek boat ramp. SLIP RENTAL available. ROOM TO PARK your boat and trailer in the driveway! Take a walk down the street (or ride one of our bikes) to see gorgeous lake views! This 3 bedroom, 3 bathroom house has what you need for your stay! Each bedroom has its own full bathroom. Remodeled kitchen, game room in the garage, smart TVs, great back deck, and much more!

Driftwood Cottage with HotTub on Lake Cumberland

Gorgeous cottage with seasonal lake view overlooking Lake Cumberland . The Marina which has boat slips, boat dock , boat rentals and restaurant are a quick jog down the hill. Enjoy the lake view from the Hot tub on the deck,amazing on even a winter day! The home has a big yard with trees for privacy . 2 bedrooms on main floor. Loft has 1 bedroom plus a day bed with trundle in open area overlooking downstairs. Outside staircase and inside spiral stairs

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.

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

Lake Cumberland State Park Villa

Fish, hike, swim in the heated pool, play putt putt golf, enjoy archery courses, horseback riding, play basketball, tennis or pickleball all while nestled in the Apple Valley Resort! Your 2 Bedroom, 2 Bath Townhome awaits! There is also a Gazebo with several picnic tables, grills, a playground, a boat shed and more!!! We look forward to hosting you, your friends & family!! Pool is closed for season.

4 bed 2 bath by Jamestown Marina

Welcome to Cocktail Cove! This 4 bedroom 2 bath house has been newly remodeled and we are excited to share it with you! You couldn’t ask for a better location when visiting Lake Cumberland! Located in Jamestown, KY, we are only 2 miles from Jamestown Marina, 2 miles from Lily Creek boat ramp, and just 5 miles from the town of Russell Springs. Literally everything you need is just minutes away!

Lily Creek Cottage

Relax with the family at this quaint, and peaceful cottage in Jamestown, Ky. @Lake Cumberland!! This cute little cottage is all you need after enjoying a fun day on the water, boating, or fishing. conveniently located only 5 minutes from Safe Harbor boat Marina (Jamestown, Ky.) and 2 miles from Lily Creek boat ramp!! Pet friendly (limit 2 pets please) Handicap accessible ramp front door.