Holiday rentals with outdoor seating in Jamestown

5 out of 5 average rating, 11 reviews

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.

Cabin in Jamestown

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.

4.99 out of 5 average rating, 134 reviews

An outdoor seating area is arranged around a fire pit, with chairs positioned for comfort. The night sky glows softly from the moonlight, casting a gentle light on the surroundings. Trees are faintly visible in the background, enhancing the serene atmosphere.

Home in Bronston

Country stay near the Falls-Polar Express Railway

Welcome to our countryside getaway nestled on almost 5 acres within 5-20 miles of Burnside, Lee's Ford, and Conley Bottom Marinas. Enjoy the day on Lake Cumberland. Come back to relax, eat, drink & be merry. Gather around the outside barbecue area and fire pit or snuggle up inside next to the fireplace, playing games or watching a movie. Whether you are on a couple's retreat, fishing buddy's getaway, or family vacation - the house and outdoor area provide plenty of room to relax and enjoy.

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.

4.9 out of 5 average rating, 178 reviews

The exterior of the tiny house is presented, featuring a clean driveway and well-maintained lawn. Four outdoor chairs are arranged in a cozy seating area, surrounded by greenery and shaded by trees. The building displays a modern design with contrasting black and white elements.

Home in Somerset

Tandy Tiny House

Welcome to Tandy Tinyhouse! This Adorable 1Br is Brand New and has everything you need! Very Modern Kitchen w/tiled backsplash, Microwave, Keurig, Refrigerator, Range and Granite Counters. LTV Flooring and 10ft Ceilings throughout. En-suite features a Barn door and Tiled Shower. Washer/Dryer Combo just off of the Kitchen Area. Amazing location 3 minutes to Downtown Somerset and 10 minutes to Lees Ford Marina. You will want to stay here again and again! Please leave mini split 68 or above

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.

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

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.

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!

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.

Apartment in Jamestown

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.

5 out of 5 average rating, 61 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 Jamestown outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

The outdoor entertainment area is illuminated at night, featuring bar seating and a television mounted above a bar. The fire pit is located at the center, providing warmth and ambiance, while a swing seat is visible in the background.

4.91 out of 5 average rating, 11 reviews

Little Indian Retreat

5 out of 5 average rating, 34 reviews

A shaded outdoor dining area features a table surrounded by chairs, set on a wooden deck. String lights hang overhead, and the expansive view of the lake and surrounding hills is visible in the background, enhancing the serene outdoor experience.

Home in Russell Springs

Welcome to your Dream Lake Home

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

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

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!

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

The exterior of a wooden cabin is presented, featuring a rustic design and a welcoming front porch. A combination of light and dark wood panels creates visual interest, while landscaped gravel areas enhance the entryway. Natural surroundings complement the tranquil lakeside atmosphere.

4.85 out of 5 average rating, 27 reviews

Lily's Paradise Lake House

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, 14 reviews

Lake Vibes

Apartment rentals with outdoor seating

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

4.98 out of 5 average rating, 44 reviews

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.

Apartment in Jamestown

New near Jamestown Dock - A

4.92 out of 5 average rating, 13 reviews

The entrance of Woodson Bend Resort is marked by a stone sign set within a landscaped garden. Lush green plants surround the sign, creating a welcoming view among the trees that provide a natural backdrop.

Apartment in Bronston

Woodson Bend Resort getaway on Lake Cumberland.

A spacious living area is highlighted by a large sectional sofa arranged around a central ottoman. A decorative rug features a geometric pattern, while light walls and tropical accents create a fresh atmosphere. The room is illuminated by natural light from sliding glass doors leading outside.

Apartment in Bronston

5 out of 5 average rating, 3 reviews

Beauty on the 7th Fairway (65-3) Golf Pool Tennis

Apartment in Pulaski County

Blue Heron (60-4) - Golf, Pool, Pickleball

4.83 out of 5 average rating, 29 reviews

The studio suite features a spacious bed with a textured blanket, complemented by rustic barn wood accents. A dining area with a wooden table and four chairs is visible, along with a fully equipped kitchen. Large windows brighten the space, framed by simple blinds.

Apartment in Burnside

The Rustic Suite (500A)Fun, Lake, Golf carts, Food

4.74 out of 5 average rating, 23 reviews

A well-lit sleeping area features a spacious bed with a white quilt and black accent pillows. Two bedside lamps provide soft lighting, while a painting hangs above the bed. A patterned chair adds to the decor, with long curtains framing the window.

Apartment in Somerset

Lake Lovers Paradise

Condo rentals with outdoor seating

Paradise By The Pool (53-3) Golf, Pool, Pickleball

The family room features two comfortable sofas and a coffee table, with large windows allowing natural light to fill the space. The dining area, visible through an open layout, contains a wooden table with chairs, adjacent to a well-equipped kitchen.

4.88 out of 5 average rating, 8 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

A spacious living area features a comfortable dark sofa with decorative pillows, a light table with a lamp, and a patterned chair. Large windows allow natural light, while a door leads to an outdoor space. A textured rug enhances the inviting atmosphere.

Green Lite Lakeview (105-1) Lake, Golf, Pool

A spacious living area features a large sectional sofa adorned with colorful cushions, complemented by an oversized bean bag. Natural light brightens the room through sliding glass doors that lead to an outdoor space, with an open-flow view of a well-equipped kitchen.

4.75 out of 5 average rating, 20 reviews

Lake Cumberland Resort Condo w/ Direct Lake Access

The entrance sign for Woodson Bend Resort is framed by natural stone and surrounded by well-maintained landscaping. Tall trees stand in the background, creating a serene setting that invites guests into the resort.

4.75 out of 5 average rating, 40 reviews

Lakefront Condo and Woodson Bend Resort

An inviting open-concept living area features comfortable seating arrangements, including a spacious sectional and recliner. Natural light enters through large windows, complementing the warm tones of the walls. The fully equipped kitchen is visible in the background, and a dining area with bar stools is accessible nearby.

4.46 out of 5 average rating, 13 reviews

On the Green (71-4) WB - Golf, Pool, Pickleball

The kitchen space features white cabinetry paired with sleek black appliances. A central island with bar seating provides a casual dining option. Natural light enters through the nearby window, illuminating the wooden countertop and hardwood flooring.

4.85 out of 5 average rating, 34 reviews

Lovely 3-bedroom lake condo with golf and a pool

A spacious living area is highlighted by comfortable seating, including two dark leather sofas and an armchair. Soft lighting is provided by two lamps on side tables. Framed artwork featuring tranquil landscapes is displayed on the wall, creating a welcoming ambiance.