Holiday rentals with outdoor seating in Jamestown

4.86 out of 5 average rating, 158 reviews

An outdoor seating area is presented on a wooden deck overlooking a serene lake view. Comfortable furniture, including a sofa and chairs, surrounds a glass-topped table. An umbrella provides shade, and a small fire pit adds to the inviting space amidst greenery.

Home in Somerset

Lakeview Blue

You will not find a better view of Lake Cumberland! Newly renovated 2022!! Previously our family home, we cherish this property. We ask anyone renting to respect the neighbors and home as we have. The Lakeview Blue House is within walking distance of Lake Cumberland, several restaurants, gas stations and a liquor store. There is a seasonally open public boat ramp directly over the hill from the home and many others including Waitsboro, Burnside Marina and Burnside Island State Park/ ramp nearby.

4.92 out of 5 average rating, 188 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

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

4.88 out of 5 average rating, 171 reviews

An aerial view captures the residence nestled amongst trees, with Pitmann Creek visible in the background. The circular driveway provides ample parking, while the surrounding landscape shows a blend of greenery and autumnal hues, offering a peaceful natural setting.

Bungalow in Somerset

Blackbeard’s Lakefront Bungalow

Blackbeard’s Bungalow is located in beautiful Somerset overlooking Pitmann creek on Lake Cumberland. Enjoy the amazing year round lake views. Three large bedrooms, two full bathrooms, great room, dining room, open kitchen , screened in porch, and double decks are all yours for rest and relaxation or quality time with those you care about. Less than 10 miles to Pulaski park, Lee’s ford marina, and Burnside marina, this is the perfect location close to all conveniences but the perfect getaway.

4.99 out of 5 average rating, 143 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

Countryside stay near Cumberland Falls-SF 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, 243 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.

5 out of 5 average rating, 13 reviews

An open living area features a cozy leather sofa and two red lounge chairs arranged around a round woven coffee table. A patterned blue and white rug anchors the space, while wooden walls and ceilings contribute to a warm ambiance. A staircase leads to the upper level.

Cabin in Russell County

HOT TUB~Dog Friendly~Boat ramp~River cabin!

Welcome to The Mariner (Cabin 3) at Cabins on the Cumberland, family traditions start here. *Private boat ramp to the Cumberland River *20 Min to Lake Cumberland *Pickleball / Basketball & Playground *NEW hot tub *Game Center w/ Pool, PingPong, Arcades, Shuffleboard *Private Firepit *Barrel Saunas *Dog-friendly *Pack-n-play & high chair NOTE: This is a cabin community of 12 cabins, we do have other cabins available for your larger groups. Read our important notes below prior to booking.

4.86 out of 5 average rating, 93 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

Jabez Gem by Wolf Creek & boat ramps, pet friendly

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!

4.91 out of 5 average rating, 81 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

Weekend at Bernie's Cabin at Lake Cumberland KY

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 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, 191 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.

4.97 out of 5 average rating, 143 reviews

A charming cabin is nestled among trees, with sunlight streaming through branches. An American flag hangs by the entrance. A hot tub is located on a wooden deck, providing a serene spot to enjoy nature. The lake can be glimpsed in the background.

Cottage in Somerset

Cozy Lakehouse with a View

Imagine waking up in the morning to the birds chirping in the woods surrounding the cabin, fixing a cup of coffee, and relaxing on the deck that provides one of the best views you will ever experience on Lake Cumberland. This cabin is perfect for a romantic getaway, or a quiet retreat with the family. Simply put, this cabin offers memories that you will cherish for a lifetime and will talk about for years to come!

5 out of 5 average rating, 70 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.

Popular amenities for outdoor seating rentals in Jamestown

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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, 35 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

4.97 out of 5 average rating, 36 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

4.77 out of 5 average rating, 153 reviews

The historic farmhouse, set in a peaceful country setting, features a welcoming front porch with rocking chairs. Lush greenery and hydrangeas frame the entrance, while the steps lead to the door beneath a gabled roof. Sunlight highlights the well-maintained exterior.

Home in Russell Springs

The Little FarmHouse

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.

4.86 out of 5 average rating, 29 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

4.7 out of 5 average rating, 20 reviews

A heated swimming pool is surrounded by lounge chairs and umbrellas, with a diving board extending over the water. The pool's clear blue water reflects the bright sky, while a building is visible in the background, providing access to additional amenities.

Home in Russell County

Lake Cumberland Ky State Park Q6

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 37 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, 54 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

Flat in Pulaski County

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

Apartment rentals with outdoor seating

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.

5 out of 5 average rating, 4 reviews

A Glimpse of the Lake (77-3) Golf Pool Pickleball

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

4.68 out of 5 average rating, 19 reviews

A living area features a spacious gray sectional sofa adorned with colorful throw pillows. A round coffee table sits on a large area rug, complemented by a unique side table. Natural light pours through the large window, with light, sheer curtains enhancing the inviting ambiance.

Apartment in Somerset

Bohemian Getaway