Holiday rentals with outdoor seating in Jamestown

The front porch features a spacious lounge chair and a classic rocking chair, inviting relaxation at sunset. Soft lighting illuminates the area, highlighting the details of the white columns and the warm tones of the evening sky visible in the background.

5 out of 5 average rating, 117 reviews

Gran's Place

This newly renovated 4th generation family farmhouse sitting on 13 acres is centrally located in Russell Springs, just minutes from Lake Cumberland. We are just off the Cumberland Parkway (a short and easy drive to both Columbia and Somerset), close to Russell County Hospital, and within a mile to most fast-food chains, restaurants, gas, and grocery. Our goal is to make your stay as enjoyable as possible while visiting the Lake Cumberland area. We do ask that there be no smoking in the home.

4.94 out of 5 average rating, 257 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.

4.85 out of 5 average rating, 106 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!

4.89 out of 5 average rating, 27 reviews

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.

Home in Jamestown

Jamestown - KY Lake Cottage | Boat Parking

Welcome to your seasonal getaway at Harbor Springs Cottage near beautiful Lake Cumberland! Inside, our three private bedrooms offer a haven of comfort for you and your guests, ensuring a restful night's sleep after a day of lake time. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Harbor Springs Cottage has got you covered. ☆Book your stay at Harbor Springs Cottage today and discover why life truly is better by the lake. Your perfect retreat awaits!☆

4.99 out of 5 average rating, 110 reviews

Home in Monticello

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 1.2 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

4.82 out of 5 average rating, 106 reviews

The cabin features a green metal roof and a welcoming front porch. Lush green grass surrounds the entrance, complemented by neatly arranged shrubs. An American flag is displayed, and large windows provide natural light, enhancing the inviting appeal of the property.

Home in Columbia

Stunning Cabin Near Green River Lake

Welcome to paradise featuring a beautiful 3 Bedroom, 2 Bath cabin with a covered front porch and private deck overlooking the serene woods. Guests can enjoy the hot tub, WiFi, and so much more. This cabin has 2 Bedrooms and a Bath on the main level including 1 King Bed and 1 Queen Bed. There is 1 Bedroom and a Bath upstairs with 2 Queen Beds. This property is within half a mile from a boat dock to Green River Lake. The nearest store is located only 3.1 miles on New Columbia Hwy.

4.92 out of 5 average rating, 126 reviews

The exterior of a charming cabin is visible among a lush, wooded setting. The cabin features a metal roof and wooden sides, with a porch that invites relaxation. A blossoming tree adds a splash of color to the serene landscape, surrounded by green foliage.

Cabin in Monticello

The Stable @ Bluegrass Gables

Enjoy some retro vibes in this converted barn. Indulge your senses, from the smell of the pine shiplap to the sounds of the wind chimes on the breezy covered porch or some vintage vinyl on the victrola turntable. Light a fire and watch the flames dance in the wood burning stove. Enjoy sips of your favorite beverage from a rocking chair with a view of the Appalachian foothills. Soak in the hot tub! Vintage china, glassware, art, vinyl, furniture, games, it's all in the details.

4.98 out of 5 average rating, 114 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

Enjoy the famous sunsets over Lake Cumberland from our spacious 48 foot deck and lower patio. This home is perfect for any family on vacation to this gorgeous area. With the nearest boat dock (Lees Ford Marina) being a mile away. Interested in biking or hiking? Pulaski County Park (4mi) is a great spot for both! After a fun day out and about come back to our newly updated kitchen, or enjoy a summer nights cruise to one of our local restaurants. We can't wait to book with you!

4.83 out of 5 average rating, 111 reviews

The exterior of the cabin showcases a distinct A-frame design, featuring wooden siding and a blue front door. Surrounding greenery adds a natural touch, while a wooden walkway leads to the entrance. The setting is tranquil, framed by bare trees.

Cabin in Russell Springs

Da Bears Den Lakeside Retreat

Nestled just above Lake Cumberland Marina (Alligator II) There’s room for everyone at this modern and rustic Lake Cabin. Our large Deck is perfect for your next retreat. This property features a King Master Bedroom, Full Bunk Room for the Kiddos, and Double Queen Beds in our spacious loft. The Kitchen is fully stocked with all the essentials and this Cabin also has Laundry Center. Linens are included. WiFi Internet and Flat Screen TV's throughout. PETS WELCOME!

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.

4.8 out of 5 average rating, 250 reviews

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 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.

4.88 out of 5 average rating, 60 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.

5 out of 5 average rating, 85 reviews

Home in Jamestown

Romantic Retreat | Fireplaces, Fire Pits & Views

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

4.94 out of 5 average rating, 137 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 cozy living area features floral patterned sofas arranged around a white coffee table. Ceiling fans provide ventilation, while nautical decor, including crossed oars, adorns the walls. Natural light fills the space from nearby windows, with a view leading into the kitchen area.

4.97 out of 5 average rating, 34 reviews

Lake Top Cabin #10

4.94 out of 5 average rating, 36 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!

4.98 out of 5 average rating, 127 reviews

Home in Somerset

Sleeps 12 · Lakeview · Arcade · Hot Tub

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.

4.97 out of 5 average rating, 39 reviews

Ina's Place

5 out of 5 average rating, 22 reviews

The image displays a cozy living area featuring a comfortable brown sofa and a glass coffee table, with large windows that provide natural light. A view of Lake Cumberland is visible through the window, showcasing the calm water and rocky shoreline.

Home in Nancy

Lake cottage; 6m walk (1,100f to water); Nancy, KY

4.95 out of 5 average rating, 62 reviews

An outdoor deck area features a wooden table complemented by an orange lantern and a rustic gray lantern. Lush green trees provide a natural backdrop, and a glimpse of the lake is visible in the distance under a clear blue sky.

Home in Wayne County

Lake House "Dar Bida" Monticello

4.99 out of 5 average rating, 167 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

Peaceful Stay near Falls, Conley Bottom & Burnside

Apartment rentals with outdoor seating

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, 37 reviews

Lake Escapes on the Square

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.

Flat in Somerset

Lake Lovers Paradise

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.

4.8 out of 5 average rating, 25 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, 4 reviews

Spacious cozy beautiful getaway.

4.83 out of 5 average rating, 18 reviews

Flat in Somerset

Location, Location, Location

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

4.5 out of 5 average rating, 12 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, 52 reviews

New near Jamestown Dock - A

Other holiday rentals with outdoor seating

5 out of 5 average rating, 27 reviews

A warm wooden interior features an open living space with a cozy couch and a round coffee table. A dining area with four chairs is positioned next to a kitchen equipped with modern appliances. Light from overhead fixtures illuminates the inviting atmosphere.

Tiny home in Bronston

The Cozy Pine Retreat

4.95 out of 5 average rating, 20 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.

4.97 out of 5 average rating, 38 reviews

A single-story house is shown, featuring a metal roof and a covered front porch with white rocking chairs. The home is set against a backdrop of a clear blue sky and green grass, contributing to a welcoming outdoor space.

Home in Jamestown

Perfectly Located Newly Remodeled 3 Bedroom Home

5 out of 5 average rating, 16 reviews

An inviting living area features wooden walls and a ceiling with a rustic finish. A leather couch and side table are positioned near a flat-screen TV. Natural light enters through sliding glass doors, while decorative taxidermy accents the space, enhancing its charming character.

Guest house in Jamestown

The Boat Haus Guesthouse

5 out of 5 average rating, 30 reviews

A wooden deck is bordered by lush greenery, featuring several seating options arranged around a central fire pit. A tranquil river is visible beyond the deck, enhancing the peaceful outdoor setting. Steps lead down from the grassy area to the deck.

Cabin in Burkesville

Dead Pecker Retreat on the River

4.87 out of 5 average rating, 67 reviews

An outdoor seating area is surrounded by trees, featuring four blue Adirondack chairs arranged around a fire pit. A hammock hangs nearby, and string lights illuminate the space, providing a cozy ambiance for relaxation.

Home in Columbia

Sleeps 4, Country setting, Lake Cumberland & Green

4.88 out of 5 average rating, 77 reviews

A modern kitchen features white walls and a spacious central island with a quartz countertop. Two wooden stools are positioned at the island, while stainless steel appliances line the perimeter. Multiple windows provide natural light, enhancing the clean and functional design.

Farm stay in Somerset

The Farmhouse at Brainard Valley Ranch