House holiday rentals in Jamestown

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.

4.86 out of 5 average rating, 154 reviews

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.

5 out of 5 average rating, 31 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.

4.99 out of 5 average rating, 134 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

Country stay near the Falls-Polar Express 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.

The exterior of a single-level lake house is displayed, featuring a modern metal roof and a combination of vertical and horizontal siding in soft blue and gray tones. A covered porch extends from the front, offering a welcoming entryway and views of the expansive yard.

4.86 out of 5 average rating, 22 reviews

Dudley Hill/Boat Ramp Near/Hot Tub/Fire Pit/Games

•NEW HOT TUB on private, covered patio •Nicely appointed, single-level lake house •Huge yard for entertainment + games •Outdoor seating w/fire pit area •Multi-family + dog friendly •3 private bedrooms + 2.5 baths •Well equipped + super clean w/laundry room •Stocked w/plenty of linens + essentials •Ample free onsite parking • Quaint lake community •5 min drive to great lake access + fishing @ Dudley Hill Boat Ramp •15 min drive to Wolf Creek Marina & (Seasonal) Fishtails Restaurant

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.

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

Country setting located 2 miles from Lake Cumberland with 3 boat ramps within an 8 mile drive. Fryman landing closest ramp to 76 Falls 2 miles,Marina @ Rowena 5.8 miles,Carter Dock Road 7.8 miles. Within 20 minute drive Grider Hill Marina and 1/2 hour drive to Dale Hollow Lake. Fire pit and outdoor gas grill supplied. We are on central time zone check in time is 4:00 PM and checkout is 11:00 AM We are pet friendly however there is a fee of $50 with a 2 pet limit.

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!

4.8 out of 5 average rating, 242 reviews

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

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 rustic home with a metal roof features a spacious porch that wraps around its exterior. Stairs lead up to the main entrance, and the porch offers areas that are screened in. A gravel area is visible at the front, providing parking space.

4.83 out of 5 average rating, 70 reviews

New Rustic home near State Dock!

Great getaway! 1 mile from State Dock entrance. This new rustic home has 3 bd, 2 bath, open kitchen, fireplace in living room, loft master bedroom, full wrap around porch with a partial screened in area with great views. We have a nice size covered porch to relax and enjoy something on the grill. This home has parking for multiple vehicles or even for a boat. Come check out our lovely home to make your lake days memorable!

5 out of 5 average rating, 61 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 modern chalet exterior features a striking combination of wood and metal, showcasing large windows that invite natural light. A small deck extends from the upper level, set against a backdrop of lush greenery. The entrance is marked by a concrete pathway leading to the main door.

4.88 out of 5 average rating, 102 reviews

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

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

Cozy studio guesthouse with beautiful oak vaulted ceiling overlooking scenic woods and creek just 10-15 minutes from boat ramp on Lake Cumberland. Covered porch around guesthouse with gas grill access. Kitchen fully stocked. Full size sofa couch, and 2 full size floor mattresses in loft. Free wifi available. Onsite boat parking available. Fire pit and fire table available-both outside. No smoking.

Popular amenities for house rentals in Jamestown

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A vibrant sunset casts a warm orange glow over the water, reflecting shimmering colors across the surface. Silhouetted trees frame the scene, while the distant shoreline creates a serene backdrop, highlighting the natural beauty of the lake view.

Pitman Pointe w/ Lake View

4.76 out of 5 average rating, 17 reviews

Home in Wayne County

Private pool, 8 person Hot tub 6 Bedrooms

5 out of 5 average rating, 11 reviews

The two-story building features a welcoming yellow entrance and expansive covered decks on both levels. A gravel driveway leads up to the property, with trees lining the background and a soft sunset sky providing a warm backdrop.

Home in Monticello

Cumberland Belle Lakehouse-5bedrm,10bed,5bath

The exterior of the cottage displays a covered porch with comfortable seating for relaxation. A propane grill is situated nearby on a concrete patio, surrounded by landscaping featuring black stones. The cottage is framed by green grass and a clear blue sky, enhancing the outdoor space.

5 out of 5 average rating, 5 reviews

White Oak Cottage - Resort Pool, Boat Slip

An open main level showcases a spacious layout with high ceilings and large windows allowing natural light. A fully equipped kitchen features a central island, while a dining area accommodates several guests around a large table. Comfortable seating areas are visible, perfect for gatherings.

Home in Burnside

4.73 out of 5 average rating, 44 reviews

Hidden Haven (109R) Fun, Pool, Lake, Pickleball

A spacious lakefront estate is shown, featuring a drive-up area and a well-maintained lawn. The house has multiple gabled roofs, large windows, and a welcoming front porch adorned with seating. A two-car garage is visible to the right.

4.75 out of 5 average rating, 24 reviews

Lakefront Sunsetter at The Villager

4.74 out of 5 average rating, 58 reviews

Home in Monticello

Private pool and hot tub overlooking the Lake !

4.9 out of 5 average rating, 10 reviews

A comfortable living area is presented, featuring a gray sofa adorned with throw pillows. A round wooden table occupies the center, topped with decorative items, including a lamp and a small book. Light filters through sheer curtains, highlighting the patterned area rug.

Home in Burnside

Kellerman’s at VillagerResort-Pool, Boat slip/dock

Weekly house rentals

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.

4.94 out of 5 average rating, 17 reviews

Retreat: Hot Tub & Huge Deck!

4.94 out of 5 average rating, 90 reviews

The exterior of the home features a well-maintained lawn with greenery surrounding a decorative sign. A welcoming door in a warm tone is complemented by white trim and multiple windows. A light fixture hangs near the entrance, illuminating the pathway.

Home in Columbia

Clayton House

5 out of 5 average rating, 5 reviews

A modern two-story house is framed by a covered porch with two chairs. The exterior features blue siding and large windows, while a small landscaped area with plants is visible in front.

Home in Russell County

The Blue Alligator

4.81 out of 5 average rating, 21 reviews

A cozy futon is viewed in the foreground, featuring decorative pillows with text. A lamp illuminates the space nearby, and textured walls are visible in the background, enhancing the room's inviting ambiance.

Home in Burkesville

The Peak at Sulphur Creek

An open concept dining and living area features a light wood ceiling and recessed lighting. A comfortable seating arrangement includes a patterned chair and a spacious sofa. The room is adorned with a decorative area rug and has natural light flowing through the window coverings.

5 out of 5 average rating, 6 reviews

Cozy by the Creek

5 out of 5 average rating, 22 reviews

The exterior of a stylish Barndaminium is showcased, featuring a blue metal siding and large glass garage door. Two stories are visible, with evenly spaced windows and a welcoming front porch adorned with seating. Green grass and trees frame the property, reflecting a serene environment.

Home in Russell Springs

NEW 4br 3ba Barndo Overlooking Lake Cumberland

A warm living area features a spacious beige sofa and a patterned armchair, with a coffee table positioned centrally. The wall-mounted television is framed by a stone fireplace. A ceiling fan adds comfort, while natural light streams in through a window above the kitchen area.

5 out of 5 average rating, 20 reviews

The Shore Great Getaway

4.89 out of 5 average rating, 19 reviews

The exterior of the home features a bold blue facade with white trim and a welcoming front porch. A spacious wooden deck is visible, surrounded by trees providing shade. Gravel drives lead up to the entrance, enhancing accessibility.

Home in Highway

Wolf River Getaway-close to dock

Private house rentals

5 out of 5 average rating, 7 reviews

The exterior of a two-story cottage is showcased, featuring a white board and batten facade. A covered porch with two brown chairs welcomes guests, while neatly trimmed bushes and a concrete driveway complete the front garden area.

Home in Russell Springs

Summer's Cottage

5 out of 5 average rating, 13 reviews

A single-story brick home is framed by lush greenery, featuring a dark exterior with a welcoming front porch and a circular window. A spacious driveway leads to an attached garage, while the surrounding lawn is neatly maintained, providing ample outdoor space.

Home in Columbia

Dale's Place

5 out of 5 average rating, 3 reviews

The Dock House

4.82 out of 5 average rating, 55 reviews

A single-story house with a light-colored exterior is featured. A large front porch leads to the entrance, which includes a welcoming entryway. The well-maintained lawn is surrounded by trees, providing a serene setting. A deck is visible on one side, extending from the house.

Home in Monticello

The Lake House at Beaver Creek

4.95 out of 5 average rating, 38 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

Aerial view showcases the Airbnb nestled among lush greenery along the shoreline of Lake Cumberland. Expansive waters are visible, framed by rolling hills and dense forests. The property includes a spacious driveway leading to a picturesque home, emphasizing a serene natural landscape.

4.71 out of 5 average rating, 85 reviews

Twin Creeks Retreat!

4.97 out of 5 average rating, 34 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!

The spacious kitchen features modern appliances, a large island with seating, and a rustic wooden ceiling that enhances the airy atmosphere. A dining area is visible with an expansive table and multiple chairs, complemented by large windows allowing natural light to fill the space.