Holiday rentals with outdoor seating in Jamestown

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, 16 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 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.

4.99 out of 5 average rating, 135 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, 238 reviews

The exterior of the cabin features a wooden facade with dark green accents. A spacious screened-in porch is accessible via a set of steps. Rocking chairs are arranged on the porch, and colorful flower beds line the base of the structure, complemented by landscaping stones.

Cabin in Burnside

The Enchanted Hideaway /Pet Friendly with Hot Tub!

Come relax at the Enchanted Hideaway Cabin just minutes from beautiful Lake Cumberland within the gated Lake Cumberland Resort. This 2 BR 2BA cabin offers much to love including open concept kitchen, dining, and living room area, washer and dryer, screened-in porches, grill, fire pit and much more! And you will love the private hot tub on the back porch! There are 3 community swimming pools in the resort with one only a short walk from the cabin. Book your perfect get-a-way today!

4.97 out of 5 average rating, 268 reviews

A small dining area is positioned in front of large windows, offering a view of the lake at sunset. A bottle and glass sit on the table, which is flanked by two benches. The warm hues of the setting sun fill the room.

Guest suite in Albany

Page's Legacy: Favorite Fall Getaway

All rooms have a view of the lake and the deck overlooks Dale Hollow. We are a mile from Wolf River Boat Dock. The suite is downstairs with a private entrance. There are walking paths that encompasses 3 acres on the property. The private deck has a fire pit for chilly mornings to enjoy coffee or relaxing evening. There are some great day trips I have added to the "Host Guidebook" Click on "More about this location" and scroll to the bottom and click on "Show Host Guidebook"

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!

4.98 out of 5 average rating, 190 reviews

A spacious entryway features a striking artwork installation on the black wall, complemented by a spiral staircase leading to the upper level. Comfortable seating includes a tufted leather chair and a plush sofa, with a round wooden coffee table at the center on a decorative area rug.

Guest house in Somerset

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

4.91 out of 5 average rating, 172 reviews

A cabin exterior is surrounded by lush green grass and trees, featuring a spacious deck with wooden railings. The light-colored siding complements the metal roof, and the entrance is framed by well-maintained landscaping. Ample parking space is visible nearby.

Cabin in Bronston

Cabin on lake Cumberland

Conveniently located just outside Somerset. Plenty of parking for boats and trailers. Boat ramp at end of the road less than .8 miles with parking. Cute cabin decorated with nautical theme. Fully furnished just bring your personal belongings. Gas grill on the patio and covered front porch for you to enjoy the mornings and evenings after a day on the lake. Owner laundries bedding and towels provided.

5 out of 5 average rating, 62 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.

4.88 out of 5 average rating, 103 reviews

A modern chalet exterior features a striking combination of wood and metal, showcasing large windows that invite natural light. A small deck extends from the upper level, set against a backdrop of lush greenery. The entrance is marked by a concrete pathway leading to the main door.

Home in Somerset

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

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

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

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

4.97 out of 5 average rating, 119 reviews

A spacious wooden deck surrounds the guesthouse, showcasing a modern architectural design with a vaulted roof. Comfortable seating and tables are arranged, complemented by potted floral arrangements. Large windows invite natural light, and the surrounding trees create a serene environment.

Home in Science Hill

TT’s Treehouse

4.98 out of 5 average rating, 104 reviews

A wooden table is positioned beneath a large window, showcasing a view of Lake Cumberland framed by autumn trees. A lamp with a nautical theme sits on the table, while decorative items add a touch of warmth to the space.

Home in Somerset

Spectacular View of Lake Cumberland- Entire House

4.8 out of 5 average rating, 243 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

Apartment rentals with outdoor seating

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

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

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

4.98 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.

Flat 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.

Flat 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.

Flat in Bronston

5 out of 5 average rating, 3 reviews

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

Superhost

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.

Flat in Somerset

4.74 out of 5 average rating, 23 reviews

Lake Lovers Paradise

Apartment 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 at 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.