Holiday rentals with outdoor seating in Jamestown

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.

A modern cabin is nestled among trees, with a snow-covered landscape creating a serene backdrop. The structure features multiple outdoor decks and illuminated pathways, enhancing the inviting appearance. Large windows reflect the surrounding nature, showcasing the home's integration with its tranquil environment.

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.

4.95 out of 5 average rating, 138 reviews

A spacious living area features a modern sofa with decorative pillows. Large opening doors showcase views of the covered porch and surrounding greenery, allowing natural light to fill the space. A wall-mounted television and fireplace are also present, enhancing the inviting atmosphere.

Home in Somerset

Garage Door to the Wilderness!

Welcome to this stylish and sleek tiny home that's perfect for modern living! With ample space to sleep 4, features a bathroom complete with a beautifully tiled custom shower. The kitchen is a chef’s delight, black cabinetry and elegant granite counters.Enjoy the seamless flow of heated tile flooring throughout, leading you to the covered back porch where you can sip your morning coffee! The back garage door offers easy access to nature’s beauty. Located 5 minutes from either town or the lake!

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.

Superhost

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

4.86 out of 5 average rating, 93 reviews

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!

5 out of 5 average rating, 42 reviews

The cabin features a spacious porch with string lights, inviting seating areas, and a private hot tub. A stone fire pit surrounded by adirondack chairs provides a cozy outdoor gathering spot. Lush green grass and gravel paths extend around the cabin, set against a sunset sky.

Cabin in Jamestown

HotTub~Riverfront~Firepit~PingPong~Lake Cumberland

Welcome to The Woodlands (Cabin 5) at Cabins on the Cumberland, your family’s new getaway tradition. *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 and we do have other cabins available for larger groups. Read our important notes below prior to booking.

4.93 out of 5 average rating, 80 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 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!

Superhost

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

4.8 out of 5 average rating, 245 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

The exterior of a single-story house is presented, featuring a light grey facade with a distinct address number. A driveway leads up to the entrance, flanked by manicured landscaping. The surrounding trees are in early spring foliage, and a clear blue sky is visible overhead.

4.99 out of 5 average rating, 86 reviews

Lake View Home-Good for Big Group-Jamestown Marina

This house has one of the most amazing views! Looking right over Jamestown and State Dock Marinas, you have a perfect morning view for coffee and can overhear the marina festivities over cocktails in the evening! Only about 7 minutes (2.6 miles) to Jamestown Marina! The most loved part of our home is the back porch and the view. We always say we bought it for the view and you will know why!! Pictures don’t do it justice.

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 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

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, 110 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

Superhost

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

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

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

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, 54 reviews

New near Jamestown Dock - B

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, 10 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

5 out of 5 average rating, 21 reviews

The open-concept kitchen and dining area blend seamlessly with the living space. Features include wooden cabinetry, a stone island with seating, and modern appliances. Natural light illuminates the area, showcasing a cozy seating arrangement by a striking stone fireplace.

Home in Nancy

Fawn Run on Lake Cumberland

4.85 out of 5 average rating, 34 reviews

A wooden railing adorned with small American flags is visible in front of a cozy cabin. Lush greenery surrounds the area, and a glimpse of outdoor seating is seen through the cabin's large windows, creating a welcoming entrance to the property.

Cabin in Jamestown

Turkey's Roost at Foggy Bottom

5 out of 5 average rating, 15 reviews

Home in Burkesville

Cabin next to Dale Hollow State Park~Boat Parking

4.96 out of 5 average rating, 26 reviews

A wooden sign hangs from a post displaying 'Lakeside Lodge' against a backdrop of a rustic cabin and lush greenery. The cabin showcases a stone chimney and a steep roof, surrounded by trees, with a gravel driveway leading up to the entrance.

Cabin in Monticello

Lakeside Lodge Cabin

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, Fishing

4.93 out of 5 average rating, 14 reviews

The exterior of the cabin features a wooden façade complemented by large windows that allow natural light to enter. A red door serves as the focal point, flanked by two tree shadows and lush greenery on a well-maintained path leading to the entrance.

Cabin in Nancy

Horse Haven

4.89 out of 5 average rating, 55 reviews

A round table is set on a porch, adorned with a patchwork tablecloth. Two metal chairs with intricate designs surround the table. A small decorative birdhouse is placed at the center, with the surrounding greenery visible through the screened area.

Cabin in Russell Springs

Cabin on the Hill