Vacation rentals with outdoor seating in Jamestown

4.95 out of 5 average rating, 235 reviews

A charming log cabin is depicted with a green metal roof and a welcoming front porch. An American flag is displayed prominently, while a patio umbrella provides shade over a table and chairs. Surrounding greenery enhances the natural setting.

Cabin in Liberty

Sandy Acres Hobbit - Near Galilean Home - Liberty

Sandy Acres Hobbit Cabin is a one bedroom 2 Log Beds with Loft via ladder... nestled in the majestic hills of Kentucky, on 30 Acres 5 miles south of Liberty. Family owned and run. Our non-smoking, pet friendly ($20), log cabin has central heat and air conditioning, Log Beds, with all the comforts of home. Cable TV-DVD player and High Speed WI-FI service. Quiet getaway. Perfect for the single, couple or small family looking for adventure. SandyAcresCabins Liberty, KY. Click on Picture for More.

5 out of 5 average rating, 15 reviews

A welcoming cabin features a spacious front porch with rocking chairs and warm lighting. A circular stone firepit is surrounded by green Adirondack chairs, inviting relaxation by the fire. The cabin is nestled among trees, providing a serene setting at dusk.

Cabin in Jamestown

Riverfront~Firepit~Fishing~20 Min Lake Cumberland

Welcome to The Anchor - Cabin 7 at Cabins on the Cumberland, your family’s new getaway tradition. *Private boat ramp to access the Cumberland River *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 *Fully stocked coffee bar included *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.

4.95 out of 5 average rating, 219 reviews

A covered deck area features comfortable seating and overlooks a lush landscape with a serene lake in the distance. Sunlight filters through the trees, illuminating the wooden flooring and creating a peaceful retreat for relaxation.

Tiny home in Monticello

*Tiny LakeView Cottage* Pets welcome! Kayaks

We welcome your fur babies!! ATV trail to lake! Ice maker! Coffee! Adorable 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. Also has an ATV trail to lake!! Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

The exterior of a new construction home is visible, featuring a blend of wood and dark siding. A spacious porch, supported by wooden beams, invites relaxation, while tall trees surround the property, enhancing the sense of seclusion. Natural landscaping complements the tranquil setting.

5 out of 5 average rating, 18 reviews

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.

A spacious living area features a large leather sectional sofa and a teal armchair, complemented by a decorative ottoman. A flat-screen television is mounted on the wall opposite a large window, with natural light illuminating the light wood flooring.

5 out of 5 average rating, 8 reviews

Lake Vibes

Your Lake Cumberland retreat! Located just minutes from Lake Cumberland, this home offers the perfect escape for your next getaway. Located just 2 miles from Jamestown Marina, with easy boat access and great proximity to fantastic restaurants, and recreation, this is the perfect spot for those who love the outdoors, adventure, or relaxation! The home offers a horseshoe drive for an easy in and out, and features a garage on site for boat storage, as well as an out building, both with electric.

4.9 out of 5 average rating, 79 reviews

A cozy living area is depicted, featuring a gray sofa adorned with decorative pillows. A mounted television is positioned on the wall, while a mirror is visible beside a door framed by light gray walls. A yellow throw blanket adds a welcoming touch to the space.

Tiny home in Nancy

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!

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.

4.92 out of 5 average rating, 13 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!☆

4.91 out of 5 average rating, 64 reviews

The exterior of a renovated A-frame cabin is surrounded by lush trees. Large glass windows provide a view into the interior. A spacious deck features comfortable seating and a patio umbrella, inviting relaxation in a natural setting.

Cabin in Jamestown

Renovated cabin minutes to Jamestown Marina

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 exterior of a modern blue house is showcased, featuring multiple large windows that allow natural light to enter. A freshly paved driveway leads up to the home, while a sign indicating the house number is positioned nearby. Lush greenery surrounds the property.

5 out of 5 average rating, 16 reviews

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.

4.96 out of 5 average rating, 114 reviews

A cozy fire pit area is surrounded by several rustic chairs, positioned on a gravel surface. The serene Cumberland River can be seen in the background, bordered by lush greenery and trees, creating a peaceful outdoor setting.

Cabin in Burkesville

The riverside Cumberland Cabin

A sweet little remote cabin located in Burkesville directly on the Cumberland River. It has a total of four queen beds. Renovated inside and out with two fire pits. Outstanding coffee bar included. It has a wifi booster and a full lineup of sports channels on Dish Network. It is the perfect get away to simply unplug and reset! 11 miles to Bodock Farms wedding venue. 19 miles to Sulpher Creek , Mikes landing and Dale Hollow State Park.

4.97 out of 5 average rating, 29 reviews

A covered outdoor seating area features a dark wicker furniture set, including four armchairs with soft cushions and a matching coffee table. A large area rug with a blue and white pattern grounds the space, while potted plants add greenery.

Apartment in Jamestown

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 modern mountain home is illuminated at night, highlighted by exterior lighting that accentuates its sleek design. A spacious deck invites outdoor relaxation, with a pergola and seating area visible. Large windows allow for glimpses of the interior, creating a warm ambiance against the night sky.