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
A comfortable living area features a brown sofa and a light gray armchair, positioned around an area rug. Nautical-themed decor is visible on the walls, including a ship's wheel and an anchor. Natural light filters through curtains, illuminating the space.
Home in Russell Springs
5 out of 5 average rating, 7 reviews

Eagle's Nest Lake Retreat

Your family will be close to everything when you stay at this centrally-located vacation home. Our newly renovated retreat is sitting less than 8 miles from the water nestled right at the heart of Lake Cumberland. Our home is fully equipped for your family and friends. We have a large driveway and there is plenty of room to park your boat, personal watercraft or trailer if you choose to dock your boat for the weekend. Our home is located just next door to the well-known Eagle's Nest RV Park.

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.

Top Guest favourite
A cabin exterior is shown, featuring a welcoming front porch with string lights, surrounded by trees. A firepit with a cozy seating area is situated nearby on gravel, creating an inviting space for gatherings. Smoke gently rises from the fire, indicating recent use.
Cabin in Jamestown
4.94 out of 5 average rating, 36 reviews

Riverfront~HotTub~Pool Table~Private Boat Ramp

Welcome to The Riverview (Cabin 6) 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 of 12 cabins, we do have other cabins available for your larger groups. Read our important notes below prior to booking.

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.

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!

Guest favourite
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.
Apartment in Jamestown
4.89 out of 5 average rating, 54 reviews

New near Jamestown Dock - B

Great getaway! 4 miles from Jamestown Marina and 10 mins from State Dock. This apartment has 2 bd, 1 bath, open kitchen, living room. This apartment sits inside a small warehouse up a set of stairs with a large open driveway to make for easy access in and out with your boat. Over all there is plenty of room to relax and enjoy your stay! * This apartment is on the 2nd floor so there will be some steps to climb to get to it.

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.

Superhost
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.
Apartment in Jamestown
5 out of 5 average rating, 13 reviews

Studio Cottage on the Square

The Cottage on Town Square is centrally located to everything you'll need on your stay in Jamestown. The cottage is located just 3 miles from the Safeharbor Jamestown Marina. The layout of our "cottage" is a studio master (King Bed) with a separate bunk room (top and bottom twins) and full bath. You will have you're own private parking in the back and there's plenty of room for your boat as well.

Popular amenities for Jamestown holiday rentals

When is the best time to visit Jamestown?

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Avg. price$252 NZD$247 NZD$249 NZD$254 NZD$289 NZD$297 NZD$297 NZD$295 NZD$261 NZD$267 NZD$289 NZD$257 NZD
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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.

  1. Airbnb
  2. United States
  3. Kentucky
  4. Russell County
  5. Jamestown