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Woodson Bend Resort getaway on Lake Cumberland.

*Price includes $10 per night additional fee charged by Woodson Bend Resort. Relaxing two-bedroom, two-bath condominium at beautiful Woodson Bend Resort on Lake Cumberland. 24-hour security, golf, swimming, exercise room, basketball, volleyball, pickleball, tennis, coin laundry, driving range, magnificent views of Lake Cumberland. Two bedrooms accommodate four guests; a futon and reclining loveseat accommodate additional guests. Golf cart rentals through the golf Pro Shop. Sorry, no pets.

The Green Mini Stay @ 92 Rentals

Located closer to town, our mini stays are best suited for someone simply needing a private and easy place to crash. We send you the door code so you can easily check yourself in at your convenience. Enjoy television on the Roku device on the tv. Our mini stays are complete with bath (and fresh towels), microwave, coffee maker and mini fridge. (Not a complete working kitchen, but a simple and small kitchenette). You’ll find you stay with us clean, comfortable, and enjoyable.

The Blue Mini Stay @ 92 Rentals

Located closer to town, our mini stays are best suited for someone simply needing a private and easy place to crash. We send you the door code so you can easily check yourself in at your convenience. Enjoy television on the Roku device on the tv. Our mini stays are complete with bath (and fresh towels), microwave, coffee maker and mini fridge. (Not a complete working kitchen, but a simple and small kitchenette). You’ll find you stay with us clean, comfortable, and enjoyable.

Lake Home at The T-Box (20-3 WB) - Golf, Pool

Welcome to Lake Home at the Tee Box – Your Lake Home Away From Home Discover Relaxation and Fun Whether you prefer gazing at the scenery from the second-story sunroom or unwinding in the cozy living room for a movie night, Lake Home at the Tee Box has it all. This charming 3-bedroom, 2-bath condo overlooks the picturesque hole #7 on the Woodson Bend Golf Course. Enjoy breathtaking views or curl up for a cozy evening, offering the perfect blend of relaxation and entertainment.

Family Lake Time (102-1) Golf, Pool, Pickleball

Welcome to Family Lake Time – Your Waterfront Condo! Discover Luxurious Lakeside Living Welcome to Family Lake Time, your exquisite 4-bedroom, 3-bath lower-level condo designed for up to 8 guests. With stunning panoramic lake views, this spacious retreat is perfect for unforgettable family getaways. The inviting living room features ample comfortable seating, creating a warm gathering space, while each uniquely styled bedroom is crafted for ultimate relaxation.

Lake Escapes on the Square

The whole group will be comfortable in this spacious and unique space located right on the square in Jamestown. Bedroom 1 - Queen Bed Bedroom 2 - Full Bed Located 3.5 miles from Jamestown Marina, 12 miles to Wolf Creek Dam, 13 miles to State Dock, 0.8 miles to Dollar General Market, walking distance to Reel Java, Giovanni’s Pizza & Snap’s Soda Shop! 2 parking space maximum NO ROOM FOR BOATS OR TRAILERS This apartment is located upstairs!

The Retro Suite (500B) Fun, Lake, Golf carts, Food

Welcome to “Retro Suite” – Your 1950s-Inspired Lakeside Getaway Step Back in Time with the Retro Suite Embark on a journey to the “good ol’ days” with our Retro Suite, a whimsical 1950s-inspired haven where bold, playful colors bring back the charm of a bygone era. From the moment you arrive, you’ll feel the nostalgia with encounters of iconic American figures and a vintage record player spinning tunes from Elvis Presley and The Beatles.

Number Two Fairway (38-4) - Golf, Pool, Pickleball

Welcome to Number Two Fairway – Your Home Away From Home Discover Relaxation and Golfing Bliss Welcome to Number Two Fairway at Woodson Bend Golf Course. This elegant condo, featuring stunning hardwood and tile flooring, is perfect for both large and intimate gatherings, with modern, cozy décor creating an inviting ambiance. After a day on the course, unwind in the expansive living room or sip a cocktail on the screened-in back porch.

Beauty on the 7th Fairway (65-3) Golf Pool Tennis

Welcome to Beauty on the 7th Fairway – Your Golfing Retreat Discover Stylish Elegance and Modern Comfort Welcome to Beauty on the 7th Fairway, a luxurious 3-bedroom, 2-bathroom condo that perfectly blends stylish elegance with modern comfort. The lavish living room, featuring a chic shiplap accent wall, smart TV, and cozy electric fireplace, invites you to unwind on the plush Lazy Boy sectional, complete with a sofa-sleeper.

The Rustic Suite (500A)Fun, Lake, Golf carts, Food

Welcome to “Rustic Suite” – Your Charming Retreat at Lake Cumberland Escape to the Rustic Suite Perched high above the breathtaking Daniel Boone National Forest, the Rustic Suite is a charming retreat that offers sweeping views of the Big South Fork section of Lake Cumberland. Whether you’re seeking a peaceful escape or an adventure-filled getaway, this studio promises both comfort and rustic elegance.

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.

Lakeside Oasis (7-2 WB) Golf, Pool, Pickleball

Welcome to Lakeside Oasis, your ideal retreat for unforgettable gatherings and peaceful escapes. This contemporary two-bedroom, one-bath condo comfortably accommodates up to six guests and features beautiful hardwood floors and stylish furnishings. Start your day with a cup of coffee on the screened-in porch, taking in the breathtaking views and the calming atmosphere of lakeside living.