Holiday rentals with outdoor seating in Jamestown

5 out of 5 average rating, 31 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.

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.

5 out of 5 average rating, 16 reviews

Riverfront~Firepit~Fishing~20 Min Lake Cumberland

Welcome to The Anchor (Cabin 7) at Cabins on the Cumberland, your family’s new 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 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.

4.93 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, 91 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!

Cottage in Russell Springs

The exterior of the cottage features a modern design with a prominent triangular roof and large front windows. A small patio area with two chairs is visible to the side of the entrance. Surrounding greenery enhances the natural setting of the property.

5 out of 5 average rating, 14 reviews

Timberview Cottage

Welcome to your perfect getaway! This brand-new, 2 bedroom, 1 bath cottage offers the ideal blend of comfort, privacy, and fun. Nestled on a peaceful, wooded 2-acre lot, you'll enjoy a serene country setting with all the conveniences of being just minutes from town and multiple Lake Cumberland marinas. Whether you're here to boat, explore, or simply unwind, this cottage makes the perfect home base. Relax in the hot tub under the stars or head out and be lake-side in no time.

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.

5 out of 5 average rating, 5 reviews

Cabin in Monticello

Hidden Creek Schoolhouse

Located between Dale Hollow Lake and Lake Cumberland, tucked in a Hollow down a quiet track, you’ll find a schoolhouse from way back. Built in 1919, cozy and sweet, with original wooden floors and charm complete. The creek hums low when the time is right, and summer skies glow soft and bright. Lakes are near if you choose to roam, but the Hollow feels like home. Spring blooms, autumn glows, winter hushes with snow; at Hidden Creek, time slows in a storybook place.

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!

4.8 out of 5 average rating, 242 reviews

A hot tub is situated on a wooden deck beneath a pergola adorned with string lights. Soft blue water glows, reflecting the warm ambiance. A dining set with light-colored chairs is visible in the background, creating a relaxed outdoor space.

Home in Russell Springs

Driftwood Cottage with HotTub on Lake Cumberland

Gorgeous cottage with seasonal lake view overlooking Lake Cumberland . The Marina which has boat slips, boat dock , boat rentals and restaurant are a quick jog down the hill. Enjoy the lake view from the Hot tub on the deck,amazing on even a winter day! The home has a big yard with trees for privacy . 2 bedrooms on main floor. Loft has 1 bedroom plus a day bed with trundle in open area overlooking downstairs. Outside staircase and inside spiral stairs

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.

4.97 out of 5 average rating, 36 reviews

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!

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.

4.89 out of 5 average rating, 53 reviews

New near Jamestown Dock - B

Great getaway! 4 miles from Jamestown Marina and 10 mins from State Dock. This apartment has 2 bd, 1 bath, open kitchen, living room. This apartment sits inside a small warehouse up a set of stairs with a large open driveway to make for easy access in and out with your boat. Over all there is plenty of room to relax and enjoy your stay! * This apartment is on the 2nd floor so there will be some steps to climb to get to it.

Popular amenities for Jamestown outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday 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

4.94 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

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

4.98 out of 5 average rating, 105 reviews

A hot tub is situated on a deck, surrounded by a wooden railing. Colorful artwork depicting Somerset, Kentucky, serves as a backdrop. Twinkling string lights hang above, casting a gentle glow, while the landscape features trees and a scenic lake view at sunset.

Home in Somerset

Lake Cumberland Luxury: Hot Tub-Arcade-Epic Views

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

4.97 out of 5 average rating, 34 reviews

A wooden deck is featured, equipped with a gas grill, a large umbrella, and a dining set that includes a table and four chairs. The surrounding trees provide a natural backdrop, enhancing the outdoor living space.

Home in Burkesville

Boating Mecca: Near Dale Hollow Lake & Golf!

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.

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.

Apartment 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.

Apartment in Russell Springs

4.45 out of 5 average rating, 11 reviews

Resort Clubhouse

An open kitchen and dining area is displayed, featuring a dining table with six chairs. The kitchen includes a range, coffee maker, and shelves with dishware. Adjacent to the area, a comfortable seating arrangement and a television are positioned, surrounded by wood-look flooring and soft wall colors.

4.98 out of 5 average rating, 44 reviews

New near Jamestown Dock - A

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

4.93 out of 5 average rating, 44 reviews

The newly constructed cabin features a welcoming wooden exterior with a spacious deck surrounded by trees. Large windows and a central chimney are visible, allowing natural light to fill the interior spaces while blending harmoniously with the forested surroundings.

Cabin in Russell Springs

Lake Daze Cabin

5 out of 5 average rating, 16 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!

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

Superhost

An aerial view captures the surrounding greenery of a wooded area with a lakeside house positioned at the bottom. Nearby, the State Dock marina is visible along the shoreline, surrounded by various boats, offering insight into the outdoor recreational opportunities available.

4.75 out of 5 average rating, 8 reviews

Harbor Hideaway! A getaway for 2 up to 14 guests

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