Holiday houses in Jamestown

5 out of 5 average rating, 30 reviews

Cabin in Columbia

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

5 out of 5 average rating, 16 reviews

Riverfront~Firepit~Fishing~20 Min Lake Cumberland

Welcome to The Anchor - Cabin 7 at Cabins on the Cumberland, your family’s new getaway tradition. *Private boat ramp to access the Cumberland River *Sleeps 6, this is ONE unit of our TRIPLEX *20 min drive to Halcomb’s Landing - access to Lake Cumberland *Firepit *2 min Creelsboro Country Store *Fully stocked coffee bar included *Pack-n-play and high chair NOTE: This is a cabin community, we do have other cabins available for your larger groups. Read our important notes below prior to booking.

5 out of 5 average rating, 18 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.

5 out of 5 average rating, 8 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.

4.9 out of 5 average rating, 79 reviews

Tiny home in Nancy

Home by Wolf Creek Marina & Boat Ramp Pets Welcome

Tiny home near Lake Cumberland, Wolf Creek Marina (4.5 miles) Dudley boat ramp (1.2 miles). Beach Grove boat ramp (1.5 miles) Harris grocery (3 miles) Mill spring battle field visitors center is close by (15 miles) 30 minute drive to the Somerset, which has breweries & restaurants. Opening soon Horse Soldier bourbon!! Hour drive to Cumberland falls park. It has a bedroom, kitchen and full shower. Bring your boat and your furry friends to our peaceful tiny home. We hope to see you soon!

4.92 out of 5 average rating, 13 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!☆

5 out of 5 average rating, 40 reviews

Guest suite in Columbia

Studio @ 219 - close to LWC, 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 College, 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!

4.91 out of 5 average rating, 64 reviews

Renovated cabin minutes to Jamestown Marina

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.

5 out of 5 average rating, 16 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.

4.92 out of 5 average rating, 49 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!

4.97 out of 5 average rating, 29 reviews

Apartment in Jamestown

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!

5 out of 5 average rating, 41 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.

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Other great holiday rentals in Jamestown

5 out of 5 average rating, 13 reviews

Kentucky Coal Cabin 2 min from Lake Cumberland

TiffanyRating, 5 stars2 weeks ago

Perfect for our group!

5 out of 5 average rating, 24 reviews

Welcome to your Dream Lake Home

KrissaRating, 5 stars1 week ago

We had such an amazing stay at Samatha’s! She was so friendly and accommodating. She worked around all of our needs since we came out of state, we had a blast! The view was also breathtaking!

5 out of 5 average rating, 20 reviews

Catch and Relax on Main!

ShaneRating, 5 stars7 months ago

Was a great stay. Really nice house and great price. Super clean as well. Was perfect for our race team while racing at Cumberland dragway. Great people and easy to check into and out of. Thanks.

5 out of 5 average rating, 22 reviews

Ina's Place

LauraRating, 5 stars5 days ago

Excellent stay. Met all our needs and then some. Only regret is that we didn’t stay long enough. We were in town for a wedding. Wish we had planned a longer stay. Very comfortable home that managed our multigenerational family (including small children) extremely well.

4.77 out of 5 average rating, 70 reviews

Twin Creeks Retreat!

CharlesRating, 5 stars1 day ago

It was very nice and clean. Everything was just like Mr. Eric said it would be. It's a very nice area to stay at easy access to any places you need to go to i will definitely be staying there again in the future thanks once again Mr. Eric for hosting me for those 3 days on short notice.

5 out of 5 average rating, 4 reviews

Harbor Hideaway! A getaway for 2 up to 14 guests

LanceRating, 5 stars1 month ago

Very nice place and Tammy was always super helpful if we had any questions. Would definitely stay here again!

5 out of 5 average rating, 109 reviews

Gran's Place

BruceRating, 5 stars5 days ago

Gransplace made us feel welcomed from the moment we stepped onto the front porch. The family memorabilia and photos was an added benefit! We would definitely recommend to anyone in the area!