Holiday rentals with outdoor seating in Jamestown

The cabin is embraced by trees and features a spacious front porch with multiple seating areas. Soft lighting illuminates the exterior, highlighting the welcoming entrance and natural surroundings. A gravel pathway leads to the porch, enhancing the rustic charm of the setting.

5 out of 5 average rating, 11 reviews

Firepit~Arcade Games~River Boat Ramp~Pickleball

Welcome to The Oar - Cabin 8 at Cabins on the Cumberland, your family’s new getaway tradition. *Private boat ramp to access the Cumberland River *Pickleball/Basketball Court & Playground *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 *Pack-n-play, 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.

5 out of 5 average rating, 32 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.

5 out of 5 average rating, 34 reviews

The exterior of a spacious cabin features a combination of light-colored siding and stone accents. A large grass area surrounds the home, complemented by a metal roof overhanging the front porch. Parking space is available on the gravel pad beside the cabin.

Cabin in Nancy

Lake Cumberland, Sauna, Fall Festivals, Wolf Creek

Looking for a relaxing lake cabin with water access for fishing, boating or swimming? How about health/fitness with our Infrared Sauna? Like Fall/Winter Festivals too? Check out our local holiday destination Bear Wallow Farm (on FB). Pumpkin Patches, Tube Rides, Hayrides, Selfie spots, fabulous foods and special seasonal beverages! Relax with the whole family at this peaceful cabin. A 1/2 mile from lake access, gravel beach, boat launch, fishing & swimming. Just 6 miles to Wolf Creek Marina.

4.93 out of 5 average rating, 238 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! 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.

4.87 out of 5 average rating, 92 reviews

A tiny home is depicted with a metal exterior and a sloped roof. A front porch area features several chairs in various colors arranged on gravel, providing a welcoming space for guests. A single white door and a nearby window are also visible.

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!

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, 20 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.

4.94 out of 5 average rating, 135 reviews

The cottage features a green metal roof and a welcoming front porch with multiple wooden rocking chairs. Two planters are positioned at either side of the entrance, and a outdoor grill is visible near the porch. A gravel path leads up to the door, with lush greenery in the background.

Home in Albany

Avery Acres

Country setting located 2 miles from Lake Cumberland with 3 boat ramps within an 8 mile drive. Fryman landing closest ramp to 76 Falls 2 miles,Marina @ Rowena 5.8 miles,Carter Dock Road 7.8 miles. Within 20 minute drive Grider Hill Marina and 1/2 hour drive to Dale Hollow Lake. Fire pit and outdoor gas grill supplied. We are on central time zone check in time is 4:00 PM and checkout is 11:00 AM We are pet friendly however there is a fee of $50 with a 2 pet limit.

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.

4.9 out of 5 average rating, 61 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!

4.97 out of 5 average rating, 36 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.

Flat 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!

5 out of 5 average rating, 63 reviews

Modern Mountain Retreat | Fireplace & Luxe Design

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.

4.87 out of 5 average rating, 23 reviews

A heated pool is surrounded by lounge chairs beneath bright blue skies, with a shaded gazebo visible in the background. Poolside amenities include umbrellas and pool steps leading into the water, creating a relaxing environment for guests.

Tower in Russell County

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.

A newly remodeled house with a dark exterior is situated on a lush green lawn, surrounded by trees. The structure features a unique roofline and several windows that offer natural light, creating a connection with the outdoor scenery.

4.96 out of 5 average rating, 45 reviews

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!

Popular amenities for outdoor seating rentals in Jamestown

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.92 out of 5 average rating, 186 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

4.95 out of 5 average rating, 19 reviews

A charming farmhouse is surrounded by lush greenery, with a spacious front yard. The entrance features two wooden doors flanked by hanging flower pots, leading to a covered porch adorned with blue seating. A concrete pathway guides visitors to the entrance.

Home in Albany

Elisi's Cozy Nook 3.2 mile from Marina Rowena.

5 out of 5 average rating, 16 reviews

The modern white house is nestled among vibrant autumn foliage, with touches of red, orange, and yellow throughout the landscape. A gravel driveway leads to the home, which features large windows and outdoor seating. A dark structure is visible in the background.

Home in Nancy

New Modern Lake House at Wolf Creek Marina

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, 22 reviews

Jamestown - KY Lake Cottage | Boat Parking

4.94 out of 5 average rating, 17 reviews

A modern two-story house features a sleek black exterior, complemented by wooden accents. The front porch includes several outdoor chairs, providing a welcoming entrance. Large windows enhance the building's design, while the surrounding trees create a natural backdrop, emphasizing the peaceful setting.

Home in Nancy

Retreat: Hot Tub & Huge Deck!

5 out of 5 average rating, 34 reviews

A living room features fully reclining furniture arranged around a patterned rug. Two lamps illuminate the cozy seating area. A wall sign reads 'LAKE LIFE.' An open view leads to the dining area, which is visible through a wide entryway.

Home in Russell Springs

Ina's Place

4.99 out of 5 average rating, 91 reviews

Home in Monticello

Hot Tub, Fire Pit, King En-suites, Holiday Ready,

4.89 out of 5 average rating, 85 reviews

A charming house is set against a backdrop of lush greenery, surrounded by tall trees. The well-maintained lawn features a manicured appearance, while the welcoming front porch is highlighted by a red entry mat. A clear blue sky complements the serene forest setting.

Home in Nancy

Waterfalls, fishing pond, lake view, and 8 acres!

Apartment rentals with outdoor seating

A spacious bed with a white and blue color scheme is positioned against a deep blue accent wall. Two bedside lamps provide soft lighting on either side. A decorative sign titled 'The Cottage' is displayed above the headboard, while a stylish rug covers the wooden floor.

Flat in Jamestown

5 out of 5 average rating, 8 reviews

Studio Cottage on the Square

A modern kitchen is equipped with stainless steel appliances, including a microwave and an oven. Wooden cabinets provide ample storage space, while a countertop offers a workspace for meal preparation. A window allows natural light, enhancing the clean and functional layout.

Flat in Albany

5 out of 5 average rating, 3 reviews

Spacious cozy beautiful getaway.

An indoor pool area features an elongated pool with clear water, surrounded by light-colored walls and several lounge chairs. A handrail provides access to the water, while large windows allow natural light to fill the space.

Flat in Russell Springs

4.45 out of 5 average rating, 11 reviews

Resort Clubhouse

4.89 out of 5 average rating, 53 reviews

A living area is showcased with a leather couch facing a flat-screen television. A coffee table is centered on a decorative rug. A wall clock and air conditioning unit are visible, while a doorway leads to additional rooms.

Flat in Jamestown

New near Jamestown Dock - B

Other holiday rentals with outdoor seating

Superhost

The cabin exterior is viewed from below, showcasing a spacious front deck with a wooden railing and potted flowers. A grill is visible at the center, surrounded by outdoor furniture. The steeply pitched roof adds architectural interest against a backdrop of greenery.

5 out of 5 average rating, 14 reviews

Kentucky Coal Cabin 2 min from Lake Cumberland

Superhost

A wooden deck extends from the cabin, featuring a single chair and a small grill. The entrance is marked by a screen door that opens to the interior. Surrounding trees provide a natural backdrop, enhancing the outdoor setting.

4.72 out of 5 average rating, 18 reviews

Wolf's Den at Foggy Bottom

The A-Frame cabin is surrounded by lush greenery, offering a tranquil setting. A welcoming wooden deck extends from the entrance, providing access to the interior. Nearby, a spacious garage is visible, maintaining the harmonious aesthetic of the natural landscape.

4.88 out of 5 average rating, 48 reviews

Lake Cumberland Cabin - Spa, Firepit, Scenic Views

4.89 out of 5 average rating, 18 reviews

The exterior of a multi-level cabin is framed by lush green trees, showcasing wooden siding and a covered porch. A set of wide stairs leads to the entrance, while a spacious wooden deck provides an area for outdoor activities.

Treehouse in Burkesville

Cabin in the Trees Burkesville - Fishing Retreat

4.96 out of 5 average rating, 25 reviews

A wooden sign hangs from a post displaying 'Lakeside Lodge' against a backdrop of a rustic cabin and lush greenery. The cabin showcases a stone chimney and a steep roof, surrounded by trees, with a gravel driveway leading up to the entrance.

Cabin in Monticello

Lakeside Lodge Cabin

4.98 out of 5 average rating, 59 reviews

A cozy living space is shown, featuring a red recliner and a beige sofa. Checkered curtains adorn the window, allowing natural light to enter. A decorative wreath hangs on the wall, and a TV is mounted above a unit, enhancing the functionality of the area.

Cottage in Monticello

Clean and cozy, only 150 yards away from water.

Yurt in Cumberland County

A yurt is positioned amidst tall trees, surrounded by a gravel pathway. The outdoor deck extends towards the wooded area, allowing for views of the landscape. A modern structure is visible nearby, complementing the natural setting.

4.88 out of 5 average rating, 82 reviews

The Caelestis Yurt