Holiday rentals with outdoor seating in Jamestown

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.

4.93 out of 5 average rating, 245 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!

4.94 out of 5 average rating, 234 reviews

A spacious deck features a glass table with seating for four, shaded by tall trees. The modern A-frame structure is visible in the background, showcasing large windows that invite natural light and views of the surrounding greenery. A gas grill can be seen off to the side.

Cottage in Somerset

Cozy Lakefront Cottage Getaway with Relaxing View

Fishing Creek Cottage overlooks Fishing Creek, a popular recreational area on Lake Cumberland and a major arm of the lake. Pulaski County Park and its beach and boat ramp can be seen across the lake. Boaters frequent the area to ski & tube, but are distant enough that noise isn't an issue. We are the last house at the end of a quiet street in a residential neighborhood, & so have relative privacy. The large deck and impressive view are frequently referenced in our guests' reviews.

A cabin living area features wooden walls and ceiling with a warm glow. A comfortable brown sofa faces a wooden coffee table, surrounded by two side chairs. A staircase leads to the loft area, and a fully equipped kitchen is visible in the background.

4.97 out of 5 average rating, 29 reviews

HOT TUB~Fishing BoatRamp~LakeCumberland~RiverCabin

Welcome to The Campsite (Cabin 4) 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, we do have other cabins available for your larger groups. Read our important notes below prior to booking.

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!

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

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

The whole group will be comfortable in this spacious and unique space located right on the square in Jamestown. Bedroom 1 - Queen Bed Bedroom 2 - Full Bed Located 3.5 miles from Jamestown Marina, 12 miles to Wolf Creek Dam, 13 miles to State Dock, 0.8 miles to Dollar General Market, walking distance to Reel Java, Giovanni’s Pizza & Snap’s Soda Shop! 2 parking space maximum NO ROOM FOR BOATS OR TRAILERS This apartment is located upstairs!

4.98 out of 5 average rating, 112 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

Unwind at our Lake Cumberland retreat—where comfort meets adventure. Soak in the hot tub, relax on lakeside swings, or challenge your crew in the game room. Inside, enjoy spacious living areas, plush bedrooms, and a fully stocked chef’s kitchen. Just minutes from shopping, dining, and Lee’s Ford Marina with boat ramp access and slip rentals available. The perfect blend of relaxation, recreation, and convenience awaits.

5 out of 5 average rating, 72 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 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, 189 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

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

4.83 out of 5 average rating, 86 reviews

Home in Nancy

Large Pond View, 2 min to Lake! Hot tub

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

4.99 out of 5 average rating, 97 reviews

A serene bedroom features a spacious bed adorned with soft linens and a decorative throw. Two windows allow natural light to fill the room, complemented by light-colored wood floors. Nightstands with lamps flank the bed, and subtle decor adds to the calming ambiance.

Home in Monticello

< 1/8 to Boat Ramp, Spa, Fire Pit, King En-suites

4.75 out of 5 average rating, 59 reviews

Home in Monticello

4 bedroom, private pool 8 person hot tub

4.98 out of 5 average rating, 40 reviews

A wooden deck is featured, equipped with a gas grill, a large umbrella, and a dining set that includes a table and four chairs. The surrounding trees provide a natural backdrop, enhancing the outdoor living space.

Home in Burkesville

Boating Mecca: Near Dale Hollow Lake & Golf!

Apartment rentals with outdoor seating

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, 12 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, 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

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

Superhost

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

5 out of 5 average rating, 27 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

4.97 out of 5 average rating, 37 reviews

The exterior of the Riverside Retreat features a charming two-story home with a gabled roof and a welcoming entrance. A stone pathway leads to the front door, framed by subtly lit landscaping and blooming flowers. Lush greenery is visible in the background, enhancing the tranquil setting.

Home in Peytonsburg

“Riverside Retreat” (New Hot Tub)

4.96 out of 5 average rating, 27 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

Cottage in Russell Springs

A modern cottage with a dark exterior is seen nestled among trees. The structure features a gabled roof, large front windows, and a welcoming front porch. An outdoor seating area is located on the left, providing a serene space to enjoy nature.

5 out of 5 average rating, 20 reviews

Crest View Cottage-Cozy LCK Home

4.93 out of 5 average rating, 15 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