Vacation rentals with outdoor seating in Jamestown

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.

5 out of 5 average rating, 11 reviews

River Boat Ramp~Arcade Games~Sauna~Pickleball

Welcome to The Oar - Cabin 8 at Cabins on the Cumberland, your family’s new getaway tradition. (ONE UNIT IN OUR TRIPLEX) *Private boat ramp to the Cumberland River *20 Min to Lake Cumberland *Pickleball / Basketball & Playground *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 important notes prior to booking.

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 homes 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.

4.86 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 homes 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!

5 out of 5 average rating, 14 reviews

Cabin in Monticello

Hidden Creek Schoolhouse

Not all escapes are found on maps; some are found in time. Tucked into a quiet hollow between Dale Hollow Lake and Lake Cumberland sits a 1919 schoolhouse where stories linger and life slows. Original wood floors whisper history, the seasonal creek hums when it pleases, and the skies put on a show in every season. Wander to the lakes or stay wrapped in the stillness…spring blooms, autumn glows, winter hushes. Hidden Creek is a storybook stay you step into, not rush through. Book early!

4.99 out of 5 average rating, 97 reviews

A spacious outdoor seating area features a comfortable sectional sofa with soft cushions and accent pillows. A coffee table, adorned with a potted plant, is positioned in front. Beyond, a firepit with multiple chairs invites relaxed gatherings, set against a backdrop of lush trees.

Home in Monticello

< 1/8 to Boat Ramp, Hot Tub, Fire Pit, King En-sui

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 0.8 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!

4.77 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

Historic farmhouse in a peaceful country setting. Home was built by World war 2 veteran! Kitchen has all your basic needs ;Crock pot, Coffee maker and toaster , washer and dryer for your convenience! The bathroom and one bedroom is on main floor and upstairs are 2 more bedrooms plus a tiny sunroom with a daybed and a trundle bed that’s great for kids. Lovely front porch where wildlife can often be seen! Convenient location with driveway right off of HWY 80 and 5 miles from town

Cottage in Russell Springs

The exterior of the cottage features a modern design with a prominent triangular roof and large front windows. A small patio area with two chairs is visible to the side of the entrance. Surrounding greenery enhances the natural setting of the property.

5 out of 5 average rating, 16 reviews

Timberview Cottage

Welcome to your perfect getaway! This brand-new, 2 bedroom, 1 bath cottage offers the ideal blend of comfort, privacy, and fun. Nestled on a peaceful, wooded 2-acre lot, you'll enjoy a serene country setting with all the conveniences of being just minutes from town and multiple Lake Cumberland marinas. Whether you're here to boat, explore, or simply unwind, this cottage makes the perfect home base. Relax in the hot tub under the stars or head out and be lake-side in no time.

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.

4.91 out of 5 average rating, 81 reviews

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!

4.97 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.

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

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

5 out of 5 average rating, 22 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

4.92 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

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

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

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

4.98 out of 5 average rating, 111 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

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

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 vacation rentals with outdoor seating

The cabin exterior is viewed from below, showcasing a spacious front deck with a wooden railing and potted flowers. A grill is visible at the center, surrounded by outdoor furniture. The steeply pitched roof adds architectural interest against a backdrop of greenery.

5 out of 5 average rating, 14 reviews

Kentucky Coal Cabin 2 min from Lake Cumberland

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.

4.85 out of 5 average rating, 34 reviews

Turkey's Roost at Foggy Bottom

4.82 out of 5 average rating, 84 reviews

Home in Nancy

Large Pond View, 2 min to Lake! Hot tub

4.96 out of 5 average rating, 28 reviews

The interior of the refurbished school bus features a cozy sleeping area with a queen bed, complemented by warm wooden accents and soft lighting. A kitchenette with burners is visible alongside a small dining area with two tables, enhancing comfort for mealtime.

Tiny homes in Monticello

Stylish Skoolie Lake Cumberland

An aerial view captures the surrounding greenery of a wooded area with a lakeside house positioned at the bottom. Nearby, the State Dock marina is visible along the shoreline, surrounded by various boats, offering insight into the outdoor recreational opportunities available.

4.78 out of 5 average rating, 9 reviews

Harbor Hideaway! A getaway for 2 up to 14 guests

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