Holiday houses in Jamestown

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Top-rated holiday rentals in Jamestown

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Guest favourite
Warm wood paneling creates a cozy interior featuring a comfortable queen bed with a plaid blanket. A navy blue sofa is centered on a decorative rug, complemented by a small coffee table. A ceiling fan and light add illumination to the inviting space.
Cabin in Columbia
4.98 out of 5 average rating, 41 reviews

Little Cabin in the Woods

Welcome to our cozy one-bedroom cabin nestled in the heart of Russell Springs /ColumbiKentucky! This charming cabin is perfect for travelers seeking tranquility and relaxation. Surrounded by lush forests you'll enjoy the gentle breezes rustling through the trees.The cabin features a comfortable queen size bed a fully equipped kitchen and a cozy living area. Outside you can unwind on the spacious deck or stargaze at night.Book now and create unforgettable memories in Kentucky's scenic countryside

Guest favourite
Cabin in Jamestown
5 out of 5 average rating, 9 reviews

Game Center~Riverfront Views~Family~Basketball

Welcome to The Buoy - Cabin 9 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.

Top Guest favourite
The front porch features a spacious lounge chair and a classic rocking chair, inviting relaxation at sunset. Soft lighting illuminates the area, highlighting the details of the white columns and the warm tones of the evening sky visible in the background.
Home in Russell Springs
5 out of 5 average rating, 116 reviews

Gran's Place

This newly renovated 4th generation family farmhouse sitting on 13 acres is centrally located in Russell Springs, just minutes from Lake Cumberland. We are just off the Cumberland Parkway (a short and easy drive to both Columbia and Somerset), close to Russell County Hospital, and within a mile to most fast-food chains, restaurants, gas, and grocery. Our goal is to make your stay as enjoyable as possible while visiting the Lake Cumberland area. We do ask that there be no smoking in the home.

Guest favourite
A light and airy interior features a combination of beige and white decor. Two black stools are positioned beside a table, with a charming wall decoration showcasing a metal design and greenery. Natural light filters through sheer curtains, enhancing the cozy ambiance.
Cottage in Monticello
5 out of 5 average rating, 105 reviews

The Cozy Cabell Cottage

It’s time for an adventure at our vacation rental, Cabell Cottage. With Lake Cumberland only 5 minutes away via the Cabell landing....really your boat is 5 minutes from being in the water; the cottage can be your base for all things fun on the lake (swimming, boating, and fishing). Did I CATCH your interest with fishing. However, if it’s a retreat you seek, the cottage is also for you as it sits in a quiet, very pretty, rural area of Wayne County, Kentucky, where 5 can sleep easily.

Guest favourite
The exterior of a charming cabin is visible among a lush, wooded setting. The cabin features a metal roof and wooden sides, with a porch that invites relaxation. A blossoming tree adds a splash of color to the serene landscape, surrounded by green foliage.
Cabin in Monticello
4.92 out of 5 average rating, 101 reviews

The Stable @ Bluegrass Gables

Enjoy some retro vibes in this converted barn. Indulge your senses, from the smell of the pine shiplap to the sounds of the wind chimes on the breezy covered porch or some vintage vinyl on the victrola turntable. Light a fire and watch the flames dance in the wood burning stove. Enjoy sips of your favorite beverage from a rocking chair with a view of the Appalachian foothills. Soak in the hot tub! Vintage china, glassware, art, vinyl, furniture, games, it's all in the details.

Top Guest favourite
A cozy studio apartment features a spacious bed layered with a textured white blanket and decorative pillows. A wooden bench sits at the foot of the bed, while a dark bookcase stands against the wall, showcasing decorative items. Natural light filters through the nearby window, framed by dark curtains.
Guest suite in Columbia
4.98 out of 5 average rating, 61 reviews

Studio @ 219 - close to LWU, lakes, parkway

Our studio apartment is a recently remodeled extension of our home. Rest easy and assured, knowing that we are right next door to help you in any way! We are located within 2 miles of Lindsey Wilson University, between Green River Lake and Lake Cumberland and within one mile of the Cumberland Pkwy. We are ready to welcome guests who are in town for events, visiting family, vacationing, or just passing through! We look forward to taking care of you while you’re traveling!

Top Guest favourite
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
4.91 out of 5 average rating, 82 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.

Superhost
Home in Jamestown
5 out of 5 average rating, 4 reviews

The Lodge

Stylish 2BR/1BA retreat with private Cumberland River access. Sleeps 6 with open-concept living, full kitchen, and pull-out sofa. Relax on the covered front & back porches, gather around the fire pit, or fish and kayak right from the property. Nestled on a quiet dead-end road yet only 15 min to Jamestown & Jamestown Marina. Perfect for families or friends seeking comfort, style, and a peaceful getaway with the whole family at this peaceful place to stay.

Guest favourite
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, 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!

Top Guest favourite
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.
Apartment in Jamestown
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!

Top Guest favourite
Home in Jamestown
5 out of 5 average rating, 73 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.

Guest favourite
A wooden ramp leads up to a welcoming front door, surrounded by a neatly trimmed lawn. Two red Adirondack chairs are positioned on either side of the ramp. A dog relaxes comfortably on the ramp, enjoying the sun.
Cabin in Jamestown
5 out of 5 average rating, 5 reviews

Lily Creek Cottage

Relax with the family at this quaint, and peaceful cottage in Jamestown, Ky. @Lake Cumberland!! This cute little cottage is all you need after enjoying a fun day on the water, boating, or fishing. conveniently located only 5 minutes from Safe Harbor boat Marina (Jamestown, Ky.) and 2 miles from Lily Creek boat ramp!! Pet friendly (limit 2 pets please) Handicap accessible ramp front door.

Popular amenities for Jamestown holiday rentals

When is the best time to visit Jamestown?

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Frequently Asked Questions

  • Do house rentals in Jamestown have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Jamestown. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Jamestown?

    Jamestown has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Jamestown?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Jamestown?

    Yes! Work meets play with ease at over 10 vacation rentals in Jamestown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Jamestown have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Jamestown. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Jamestown?

    Experience the best of Jamestown with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Jamestown have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Jamestown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Jamestown have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Jamestown. Enjoy a tailored experience with all the comforts you desire.

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  5. Jamestown