We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

House vacation rentals in Jamestown

Find and book unique houses on Airbnb

Top-rated house rentals in Jamestown

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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.

Home in Somerset

4.87 out of 5 average rating, 151 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.

Top guest favorite

Home in Jamestown

5 out of 5 average rating, 29 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.

Top guest favorite

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

4.97 out of 5 average rating, 114 reviews

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!

Top guest favorite

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

4.99 out of 5 average rating, 129 reviews

Countryside getaway near Conley & Burnside

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.

Top guest favorite

A spacious living area features a large leather sectional sofa and a teal armchair, complemented by a decorative ottoman. A flat-screen television is mounted on the wall opposite a large window, with natural light illuminating the light wood flooring.

Home in Jamestown

5 out of 5 average rating, 13 reviews

Lake Vibes

Your Lake Cumberland retreat! Located just minutes from Lake Cumberland, this home offers the perfect escape for your next getaway. Located just 2 miles from Jamestown Marina, with easy boat access and great proximity to fantastic restaurants, and recreation, this is the perfect spot for those who love the outdoors, adventure, or relaxation! The home offers a horseshoe drive for an easy in and out, and features a garage on site for boat storage, as well as an out building, both with electric.

Top guest favorite

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

4.98 out of 5 average rating, 103 reviews

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!

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.

Home in Jamestown

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 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.

4.94 out of 5 average rating, 134 reviews

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.

Home in Jamestown

4.9 out of 5 average rating, 60 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!

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, 241 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.

Home in Jamestown

4.99 out of 5 average rating, 85 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.

Top guest favorite

Home in Jamestown

5 out of 5 average rating, 59 reviews

Midnight Pearl

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Jamestown house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

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

5 out of 5 average rating, 11 reviews

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

Top guest favorite

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.

Home in Somerset

5 out of 5 average rating, 5 reviews

White Oak Cottage - Resort Pool, Boat Slip

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.

Home in Somerset

4.75 out of 5 average rating, 24 reviews

Lakefront Sunsetter at The Villager

Home in Monticello

4.74 out of 5 average rating, 58 reviews

Private pool and hot tub overlooking the Lake !

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

4.9 out of 5 average rating, 10 reviews

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

A spacious living area is highlighted by a high vaulted ceiling and a striking spiral staircase. Light-colored furnishings and neutral walls create an open atmosphere, while natural light floods through large windows, showcasing a cozy seating arrangement and a central coffee table.

Home in Burnside

4.89 out of 5 average rating, 57 reviews

Hillside Haven (108E) Fun, Lake, Golf carts, Pool

A spacious patio area features a large smoker and gas grill. In the background, an in-ground pool is visible, complete with a slide and surrounded by a secure fence. Lush trees provide shade, and the sky is clear with a hint of blue.

Home in Somerset

5 out of 5 average rating, 5 reviews

Cumberland Classic/Boat Ramp/Private Pool/Bar/City

A charming white bungalow is framed by a well-maintained lawn and colorful flower beds. A red roof adds a pop of color, and the welcoming entrance features a brick pathway leading to the front door. American flags adorn the porch, enhancing the inviting exterior.

Home in Somerset

4.83 out of 5 average rating, 23 reviews

Burnside Bungalow, w/ dock, pool & firepit

Weekly house rentals

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.

5 out of 5 average rating, 21 reviews

Fawn Run on Lake Cumberland

A charming cottage is nestled among greenery, offering a welcoming porch with seating. The roof is designed with a warm red hue that complements the natural surroundings. The mountains in the background provide a serene view, enhancing the outdoor atmosphere.

Home in Whitley City

5 out of 5 average rating, 4 reviews

Lake Cumberland Forest Cottage!

Top guest favorite

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.

4.94 out of 5 average rating, 18 reviews

Elisi's Cozy Nook 3.2 mile from Marina Rowena.

A one-story farmhouse is shown under a clear blue sky, featuring a light-colored exterior and a metal roof. A wide driveway leads to the carport, with well-maintained greenery surrounding the property and colorful flower beds at the base of the porch.

Home in Greensburg

4.96 out of 5 average rating, 28 reviews

Hillview Haven

Top guest favorite

Home in Monticello

4.99 out of 5 average rating, 89 reviews

< 1/8 Mile to Ramp, Two King Suites, Spa, Fire Pit

The exterior of a charming home showcases a welcoming front porch with two black rocking chairs. Lush greenery and neatly arranged flower beds enhance the inviting entrance. A pathway leads to the door, with a vast lawn extending in the background under a clear blue sky.

Home in Monticello

4.88 out of 5 average rating, 25 reviews

Cozy farmhouse close to lake!

A charming house is set against a backdrop of lush greenery, surrounded by tall trees. The well-maintained lawn features a manicured appearance, while the welcoming front porch is highlighted by a red entry mat. A clear blue sky complements the serene forest setting.

4.9 out of 5 average rating, 81 reviews

Waterfalls, fishing pond, lake view, and 8 acres!

Top guest favorite

A spacious wooden deck showcases a hot tub with jets, surrounded by outdoor seating, including chairs arranged in a circle. The backdrop features a peaceful landscape of trees and open pasture, with soft evening light enhancing the serene atmosphere.

5 out of 5 average rating, 31 reviews

Cozy fall retreat near lake w/hot tub + fire pit

Private house rentals

Top guest favorite

A wooded exterior view of a single-story home is shown, featuring a large porch that spans the front. Multiple windows allow for natural light, while a gravel pathway leads up to the entrance. Surrounding trees create a sense of seclusion.

Home in Byrdstown

5 out of 5 average rating, 15 reviews

Covered Slip with Star Point Dale Hollow Home

Top guest favorite

A spacious living area features a dual reclining loveseat and a comfortable sofa, complemented by a large area rug. Natural light enters through the windows, and a dining table is visible in the background, enhancing the cozy ambiance.

Home in Campbellsville

4.95 out of 5 average rating, 44 reviews

Della’s Delight

Top guest favorite

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

4.94 out of 5 average rating, 89 reviews

Clayton House

A modest green house is situated on a grassy lawn, featuring a flat front yard. Steps lead to a welcoming porch with two red chairs, inviting relaxation. The house is framed by a large tree, and a clear sky can be seen above.

Home in Highway

4.95 out of 5 average rating, 56 reviews

Little Green House of Shipley

Top guest favorite

The exterior shows a ranch-style home nestled among trees, featuring a covered porch with comfortable wicker seating and decorative pillows. The path made of stone leads to the entrance of the home, which is surrounded by lush greenery and natural landscape.

Home in Byrdstown

5 out of 5 average rating, 18 reviews

Dale Hollow Lake Moosehead Lodge

Top guest favorite

The exterior of the home features a welcoming porch with outdoor seating, surrounded by lush greenery. A paved driveway leads to the garage, with ample grassy area nearby. The architecture includes a combination of brick and siding, complemented by a clear blue sky overhead.

Home in Columbia

4.96 out of 5 average rating, 27 reviews

Three-A Hideaway

Top guest favorite

A charming yellow house is situated on a grassy area near a tranquil body of water. The property displays a green metal roof and features a small patio with a black table and chairs. Nearby trees provide shade and natural beauty.

Home in Monticello

4.96 out of 5 average rating, 56 reviews

Vacationers delight at Conley Bottom

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

5 out of 5 average rating, 22 reviews

NEW 4br 3ba Barndo Overlooking Lake Cumberland

Quick stats about house rentals in Jamestown

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
20 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool