House holiday rentals in Jamestown

4.93 out of 5 average rating, 215 reviews

A cottage is seen surrounded by vibrant autumn foliage, with a gravel driveway leading to the entrance. The architecture features a gabled roof and a spacious front porch, providing an inviting entry point to the home.

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 firepits outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

LocationValueQuiet

5 out of 5 average rating, 4 reviews

The Lake Nest Off Jamestown Square - Hot Tub!

Enjoy the HOT TUB at The Lake Nest! - Walking distance of town square to restaurants via sidewalk close by - Approx. 4 miles to Jamestown Marina - 3 miles to Lily Creek Boat Ramp Beautiful neighborhood in town & close to lake - 2 bedroom with 3 beds (1 King, 1 Queen & 1 Queen Sleeper Sofa) - 1 full bath - Fully equipped kitchen - Hot tub - Plenty of parking & more! No parties, no smoking, no pets, etc. Note: 1 security camera on the front porch for security purposes only. No other cameras.

LocationAccuracyQuiet

5 out of 5 average rating, 30 reviews

The Bourbon House - No Cleaning Fees

Take it easy at this unique Kentucky Bourbon themed getaway only 10 minutes away from Lake Cumberland via the Jamestown Marina with No Cleaning Fees. 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.

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A screened porch featuring a mix of red and blue chairs arranged around a table, surrounded by large windows that overlook a lush green setting. Soft lighting is provided by hanging bulbs, enhancing the inviting space.

4.91 out of 5 average rating, 32 reviews

Jamestown - KY Lake Cottage | Boat Parking

Welcome to your seasonal getaway at Harbor Springs Cottage near beautiful Lake Cumberland! Inside, our three private bedrooms offer a haven of comfort for you and your guests, ensuring a restful night's sleep after a day of lake time. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Harbor Springs Cottage has got you covered. ☆Book your stay at Harbor Springs Cottage today and discover why life truly is better by the lake. Your perfect retreat awaits!☆

FamilyLocationIndoor spaces

4.99 out of 5 average rating, 114 reviews

Home in Monticello

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 1.2 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

FamilyLocationDecor

4.82 out of 5 average rating, 111 reviews

The cabin features a green metal roof and a welcoming front porch. Lush green grass surrounds the entrance, complemented by neatly arranged shrubs. An American flag is displayed, and large windows provide natural light, enhancing the inviting appeal of the property.

Home in Columbia

Stunning Cabin Near Green River Lake

Welcome to paradise featuring a beautiful 3 Bedroom, 2 Bath cabin with a covered front porch and private deck overlooking the serene woods. Guests can enjoy the hot tub, WiFi, and so much more. This cabin has 2 Bedrooms and a Bath on the main level including 1 King Bed and 1 Queen Bed. There is 1 Bedroom and a Bath upstairs with 2 Queen Beds. This property is within half a mile from a boat dock to Green River Lake. The nearest store is located only 3.1 miles on New Columbia Hwy.

ValueFamilyComfort

4.87 out of 5 average rating, 137 reviews

Home in Nancy

Large Pond View, 2 min to Lake! Hot tub

Cozy 3 bedroom house w Large pond view and only 2 min to Lee’s Ford Marina @ the Lake! Outdoor Living at the fullest! Featuring an outdoor kitchen, blackstone grill, 2 on deck propane fire pits, 2 large smart TVs, plenty of seating!!! a wood fire pit just steps away, we don’t provide propane, if it’s there use it, not u have to re-fill King Bed in master Full Bed in guest Queen Bed in Loft w ladder access, not ideal for seniors or small children WiFi Hot tub is working

LocationFamilyAmenities

4.77 out of 5 average rating, 162 reviews

The historic farmhouse, set in a peaceful country setting, features a welcoming front porch with rocking chairs. Lush greenery and hydrangeas frame the entrance, while the steps lead to the door beneath a gabled roof. Sunlight highlights the well-maintained exterior.

Home in Russell Springs

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

ValueFamilyBarbecue

5 out of 5 average rating, 11 reviews

Charming A-frame with Lake Cumberland Views

Step back in time and unwind at this charming A-frame lakeside house, where stunning lake views and a groovy 70s vibe await! Nestled right by the water overlooking Jamestown Marina, just a few miles from the boat ramp. This mid-century gem is the perfect blend of nostalgic style and modern comfort. Whether you're relaxing on the deck, watching the sun set over the water, or curled up inside with a good book, you’ll feel the peace and nostalgia that this retro paradise offers.

ValueLocationSleep quality

The kitchen features a modern design with white cabinets and granite countertops. Stainless steel appliances are showcased, alongside open shelving displaying various dishware. Four blue metal stools are positioned around the kitchen island, and a window allows natural light to enter.

4.91 out of 5 average rating, 69 reviews

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!

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5 out of 5 average rating, 3 reviews

Rack N' Reel Retreat-Jamestown Marina - No Animals

A rustic, fun-filled getaway just 1.5 miles from Jamestown Marina on Lake Cumberland—perfect for families, fishermen, or a guys' retreat. This home features a full-size pool table, dart board, and plenty of parking for boats and trailers. The walls are decorated with a collection of mounted animals from around the world, giving the house a trophy-lodge atmosphere. Multiple common areas to spread out and relax, but still feel like you're all together!

LocationHospitality

A rustic home with a metal roof features a spacious porch that wraps around its exterior. Stairs lead up to the main entrance, and the porch offers areas that are screened in. A gravel area is visible at the front, providing parking space.