House holiday rentals in Jamestown

4.87 out of 5 average rating, 139 reviews

Lakeview Blue

You will not find a better view of Lake Cumberland! Newly renovated 2022!! Previously our family home, we cherish this property. We ask anyone renting to respect the neighbors and home as we have. The Lakeview Blue House is within walking distance of Lake Cumberland, several restaurants, gas stations and a liquor store. There is a seasonally open public boat ramp directly over the hill from the home and many others including Waitsboro, Burnside Marina and Burnside Island State Park/ ramp nearby.

4.92 out of 5 average rating, 169 reviews

Home in Monticello

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

5 out of 5 average rating, 17 reviews

Home in Jamestown

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.

4.97 out of 5 average rating, 33 reviews

The Bourbon House Newly Refreshed Family Friendly

The Bourbon House is close to everything, making it easy to plan your visit. Located within 10 min or less of 6 boat ramps, less than 5 min to downtown, Master Musician Festival, Somernites Cruise, SCC, The Center and the airport. 10 min to Somersplash and Cal Ripken baseball/softball complex. Huge yard for outdoor activities and boat parking. Gameroom for the kids and kids at heart. Basketball and Fire-pit. We welcome your family to enjoy our home and the beautiful Lake Cumberland Area.

4.98 out of 5 average rating, 65 reviews

Home in Nancy

Prather Place,Spacious,Lake View,5min to Marina

Enjoy breathtaking lake views from almost every room in the house. Very open floor plan with huge kitchen/dining/living room space. Four bedrooms to sleep 11 comfortably plus additional reclining sofas on main level. Complete game room in basement with custom bar. The theater room has the largest of 8 TV's in the house at a whopping 65 inches. Over 2,000 square feet of decking with cable railing to not spoil any of the unobstructed year round views. This truly is "THE" Lake Cumberland rental.

Superhost

4.57 out of 5 average rating, 7 reviews

Take It Easy@The Easy Peasy

•Vintage 40's farmhouse w/fabulous private pool (closed for season)+ hot tub area •Centrally-located, 2 min. to boat ramp+ 7 to marina • Hidden speak-easy themed basement bar w/pool + poker tables, shuffle board,+ more (search home for entrance+code) •Equipped country kitchen+sunroom w/drink fridge, games,+ coffee bar. •Unique attic space for family fun (lake house+camp themed w/games+movies) • 5 BR, 2 full baths-1st retro styled w/soaking tub, 2nd w/double sink+walk-in shower • Pet friendly

4.83 out of 5 average rating, 53 reviews

Home in Nancy

Little blue house on the lake

Brand new wrap around deck for 2024 for outdoor enjoyment or relax in covered sunroom. Lakeside retreat where you can unwind after a day on the lake or just enjoy peaceful country living. This charming cabin-style home features 3 bedrooms and 2 bathrooms with the primary located on the main floor and 2 bedrooms with a jack and jill bathroom upstairs. Located just a mile from a boat ramp, 6-minute boat ride to Conley Bottom or 15 minute car ride to Lee’s Ford Marina or Pulaski County Park.

5 out of 5 average rating, 15 reviews

Home in Bronston

Cozy Lakehouse – ZERO Cleaning Fee, Pet Friendly!

Discover an unforgettable escape at our breathtaking Burnside vacation home, where every moment becomes a cherished memory. • Nestled on the shores of Lake Cumberland, offering breathtaking lake views. • Luxurious amenities: Spacious 4BR, beautiful deck, screened-in sunroom with a view! • Endless entertainment: Fire pit & fully equipped game room for all ages. • Relaxation awaits: with a serene patio deck & modern comforts. • Ideal for large groups: Accommodates 14 guests, pet-friendly.

4.97 out of 5 average rating, 29 reviews

Home in Russell Springs

Lake Top Cabin #10

Completely remodeled lake view home at top of Lake Cumberland Marina. A spacious covered porch with a swing for those summer days and nights. 2 picnic tables and a grill for outdoor grilling days. A large deck with stunning views of the lake. Perfect for enjoying your morning coffee or evening wine after a great day on the lake. Perfect for large families or groups. Sleeps 10. Pets are welcome. Backyard is spacious for kids to play. Plenty of parking for your boats and vehicles. .

4.96 out of 5 average rating, 53 reviews

Home in Monticello

Vacationers delight at Conley Bottom

Don’t let the price fool you. We do Vacation right in this home. Less than a quarter mile from Conley Bottom Marina, this house is great for anyone looking to get away for the weekend. Your boat can be kept in the driveway, we have a golf cart you can rent during your stay, as well, to explore the area and drive down to the marina. Conley Bottom offers everything from the boat ramp, boat rentals, water sports, fishing. Five golf courses located within a half hour of the house

4.98 out of 5 average rating, 95 reviews

Spectacular View of Lake Cumberland- Entire House

Enjoy the famous sunsets over Lake Cumberland from our spacious 48 foot deck and lower patio. This home is perfect for any family on vacation to this gorgeous area. With the nearest boat dock (Lees Ford Marina) being a mile away. Interested in biking or hiking? Pulaski County Park (4mi) is a great spot for both! After a fun day out and about come back to our newly updated kitchen, or enjoy a summer nights cruise to one of our local restaurants. We can't wait to book with you!