Vacation rentals in Jamestown

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Top-rated vacation rentals in Jamestown

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

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Top guest favorite
The exterior of a new construction home is visible, featuring a blend of wood and dark siding. A spacious porch, supported by wooden beams, invites relaxation, while tall trees surround the property, enhancing the sense of seclusion. Natural landscaping complements the tranquil setting.
Home in Jamestown
5 out of 5 average rating, 33 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
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, 117 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 favorite
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.
Home in Jamestown
4.88 out of 5 average rating, 24 reviews

Jamestown - KY Lake Cottage | Boat Parking

Welcome to your seasonal getaway at Harbor Springs Cottage near beautiful Lake Cumberland! Inside, our three private bedrooms offer a haven of comfort for you and your guests, ensuring a restful night's sleep after a day of lake time. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Harbor Springs Cottage has got you covered. ☆Book your stay at Harbor Springs Cottage today and discover why life truly is better by the lake. Your perfect retreat awaits!☆

Superhost
Cabin in Jamestown
5 out of 5 average rating, 3 reviews

Bee Hive Cabin at Lake Cumberland KY

Step into this bright and open, cozy cabin retreat. With 3 comfy queen beds, you’ll have plenty of space to unwind. Out back, the cabin borders peaceful woods where deer often wander by. Gather around the cozy fire pit under the stars, fire up the grill for a cookout, and make memories that last. Less than 2 miles from Jamestown Marina and Lily Creek boat ramps, 15 miles to Wolf Creek Dam. Whether you’re here to fish, boat, hike, or simply relax, The Bee Hive is the perfect home base.

Guest favorite
Home in Jamestown
5 out of 5 average rating, 6 reviews

Charming A-frame with Lake Cumberland Views

Step back in time and unwind at this charming A-frame lakeside house, where stunning lake views and a groovy 70s vibe await! Nestled right by the water overlooking Jamestown Marina, just a few miles from the boat ramp. This mid-century gem is the perfect blend of nostalgic style and modern comfort. Whether you're relaxing on the deck, watching the sun set over the water, or curled up inside with a good book, you’ll feel the peace and nostalgia that this retro paradise offers.

Top guest favorite
The exterior of the cottage features a modern design with a prominent triangular roof and large front windows. A small patio area with two chairs is visible to the side of the entrance. Surrounding greenery enhances the natural setting of the property.
Cottage in Russell Springs
5 out of 5 average rating, 21 reviews

Timberview Cottage

Welcome to your perfect getaway! This brand-new, 2 bedroom, 1 bath cottage offers the ideal blend of comfort, privacy, and fun. Nestled on a peaceful, wooded 2-acre lot, you'll enjoy a serene country setting with all the conveniences of being just minutes from town and multiple Lake Cumberland marinas. Whether you're here to boat, explore, or simply unwind, this cottage makes the perfect home base. Relax in the hot tub under the stars or head out and be lake-side in no time.

Top guest favorite
Home in Jamestown
5 out of 5 average rating, 27 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.

Guest favorite
Home in Jamestown
4.9 out of 5 average rating, 63 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 favorite
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, 88 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
A modern mountain home is nestled among trees, showcasing a blend of wood and stone elements. A cozy fire pit area with chairs is positioned in the foreground, inviting relaxation. The house features large windows that reflect warm outdoor lighting in the evening.
Home in Jamestown
5 out of 5 average rating, 78 reviews

Romantic Retreat | Fireplaces, Fire Pits & Views

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 favorite
A heated pool is surrounded by lounge chairs beneath bright blue skies, with a shaded gazebo visible in the background. Poolside amenities include umbrellas and pool steps leading into the water, creating a relaxing environment for guests.
Tower in Russell County
4.88 out of 5 average rating, 25 reviews

Lake Cumberland State Park Villa

Fish, hike, swim in the heated pool, play putt putt golf, enjoy archery courses, horseback riding, play basketball, tennis or pickleball all while nestled in the Apple Valley Resort! Your 2 Bedroom, 2 Bath Townhome awaits! There is also a Gazebo with several picnic tables, grills, a playground, a boat shed and more!!! We look forward to hosting you, your friends & family!! Pool is closed for season.

Guest favorite
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.
Home in Jamestown
4.96 out of 5 average rating, 49 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 Jamestown vacation rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Jamestown?

    Jamestown has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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.

  • Are there pet-friendly vacation rentals in Jamestown?

    Four-legged friends are welcome in Jamestown. Choose from more than 10 vacation rentals for guests traveling with pets.

  • 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.

  • 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.

  • 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.

  • 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.

Quick stats about vacation rentals in Jamestown

  • Total vacation rentals

    Explore 30 vacation rentals in Jamestown

  • Nightly prices starting at

    Jamestown vacation rentals start at G$16,768 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,080 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Jamestown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Jamestown rentals

  • 4.9 Average rating

    Jamestown stays are highly rated by guests—averaging 4.9 out of 5!

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