Holiday rentals in Jamestown

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Top-rated holiday rentals in Jamestown

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Guest favourite

Tiny home in Monticello

4.96 out of 5 average rating, 200 reviews

*Tiny LakeView Cottage* ATV trail to lake~Kayaks

We welcome your fur babies!! ATV trail to lake! Ice maker! Coffee! Adorable tiny house with two decks & bonfire pit overlooking Lake Cumberland! It is located in Monticello, Ky, in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. On a dead end street, so very peaceful. Also has an ATV trail to lake!! Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

Guest favourite

Cabin in Jamestown

5 out of 5 average rating, 5 reviews

Riverfront View~Boat Ramp~Foosball~Family Friendly

Welcome to The Buoy - Cabin 9 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.

Superhost

Home in Jamestown

4.86 out of 5 average rating, 22 reviews

Lily's Paradise Lake House

Wanting to plan a getaway with friends and family? Let Lily's Paradise take care of you. Our lake house is here to help you unwind and have fun. Our lake house is located minutes away from the beautiful Lake Cumberland. We are located in the center of Jamestown and only minutes away from Russell Springs and Somerset. Enjoy time at the lake only 3 miles from Lily Creek Boat Ramp, 1 mile from Pepe's Mexican Grill, 2.5 miles from Mini Indy, 0.8 miles from Dollar General Market and much more.

Guest favourite

Home in Jamestown

4.86 out of 5 average rating, 7 reviews

Harbor Springs 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!☆

Guest favourite

Home in Jamestown

5 out of 5 average rating, 7 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 favourite

Home in Jamestown

4.91 out of 5 average rating, 44 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!

Guest favourite

Rental unit in Jamestown

4.96 out of 5 average rating, 26 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

Cabin in Jamestown

4.89 out of 5 average rating, 56 reviews

Renovated cabin minutes to Jamestown Marina

Cozy renovated cabin. New 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!

Guest favourite

Rental unit in Jamestown

4.94 out of 5 average rating, 18 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.

Guest favourite

Home in Jamestown

4.94 out of 5 average rating, 36 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!

Superhost

Cabin in Jamestown

4.88 out of 5 average rating, 24 reviews

Lake Cumberland cabin w/ spa,firepit & ramp access

Escape to the enchanting "A Frame of Mind," an idyllic A-Frame cabin nestled within the prestigious estate section of Clifty Creek Subdivision on the serene shores of Lake Cumberland. This carefully curated haven promises a harmonious blend of A-Frame charm and contemporary luxury, providing an unparalleled retreat for those seeking a truly immersive lakeside experience.

Guest favourite

Chalet in Liberty

4.9 out of 5 average rating, 126 reviews

Horse & Buggy Country Inn

Nestled on 3 acres in BEAUTIFUL Amish & Mennonite country...this ADORABLE chalet is the PERFECT getaway! Only minutes away from the local Amish & Mennonite stores! Only 6 miles from the Famous Bread of Life Cafe! Within 1 mile from The Galilean Children’s Home! Just minutes away from beautiful lake Cumberland and green river lake