Holiday rentals with a kayak in Lake Cumberland

5 out of 5 average rating, 9 reviews

Cumberland Belle Lakehouse 9bedroom,20bed,7bath

Lake Cumberland - 9 bedrooms 7 baths, 20 beds. Great for big groups. New SwimSpa (large hot tub/small lap pool) & sauna! 1/2 mile from Beaver Creek Marina. 2 Large decks, 1 of which is covered, 2 full kitchens, 2 living rooms and outdoor/ indoor dining for up to 30+. Lots of games (skeeball, popashot, arcade, air hockey, etc). 1st floor has no stairs. Must be comfortable with stairs for the 2nd floors. Plenty of boat/truck parking. Only 8 miles to town. View Q R Code to tour & see floor plan.

4.95 out of 5 average rating, 219 reviews

Tiny home in Monticello

*Tiny LakeView Cottage* Pets welcome! 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.

5 out of 5 average rating, 26 reviews

Cabin in Russell Springs

Luxury Secluded Retreat at Wolf Creek Marina

Timber Ridge Lodge @ Wolf Creek Marina is a private retreat secluded in nature. Situated on over 5 acres only 1.5 mi to Wolf Creek Marina and ramp, this custom built timber frame home sleeps 16. Gorgeous kitchen, covered wrap around decks high in the trees. Two main private suites on the first floor, spacious 2nd floor bedroom with 2 queen beds and open 3rd floor with 4 queen beds. Come see the stars, visit the lake and make memories! Don't have a boat? No problem, boat rentals are close by!

4.85 out of 5 average rating, 26 reviews

Home in Jamestown

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.

Home in Columbia

4.81 out of 5 average rating, 31 reviews

Tranquility Lake Getaway w/ Hot Tub on 27 Acres!

This off-the-beaten-path, ruggedly beautiful Columbia vacation rental will make for a trip you won't forget! Boasting 4 bedrooms, 2.5 bathrooms, and a private deck with stunning views, this home is perfect for travelers looking for peace and solitude while being surrounded by nature. Help yourself to a soak in the hot tub, and relax by the fire in the cozy great room. Do some kayaking on the lake, explore a hiking trail, or visit Lake Cumberland and cruise over a thousand miles of coastline!

5 out of 5 average rating, 20 reviews

Home 0.2 miles from boat ramp with game room

Relax and get away with your whole family at our newly remodeled lake home! We are located 0.2 miles from the nearest Lake Cumberland boat ramp. We have plenty of driveway space to park your boat. We offer an adorable master bedroom with your own private bathroom. Our garage is filled with indoor and outdoor games for all ages. The area is known for its welcoming atmosphere and small community hospitality. We are located 12 miles from Safe Harbor and 19 miles from Conley Bottom Resort.

4.98 out of 5 average rating, 64 reviews

Farm stay in Somerset

23 Acre Lake Cumberland: Boats & Fishing Oasis

Escape to a 5-star, 23-acre private lake estate, your ultimate outdoor retreat by Lake Cumberland.. Enjoy our 3-acre fishing pond with all gear provided, kayaks and boats. Relax in a luxurious 8-person hot tub, savor meals on Traeger & egg grills & 2 fire-pits. Inside, find a cozy fireplace, high-speed Wi-Fi, Smart TVs, full bath and half bath plus a gourmet kitchen. Experience Lake Cumberland with our rentals, and let me be your guide to the best hidden gems. Your dream vacation awaits!

Home in Nancy

4.82 out of 5 average rating, 11 reviews

Cumberland Cabin

Escape to our cozy cabin nestled on the serene shores of Lake Cumberland. Perfect for a relaxing getaway, this charming retreat offers modern amenities, and easy access to outdoor adventures. Whether you're looking to unwind or explore, our cabin provides the ideal setting for a memorable vacation. This property offers fiber optic Internet. Boat ramp less than a quarter of a mile off the driveway. Very short boat ride to Conley Bottom Marina which is one of Cumberlands best Marinas.

5 out of 5 average rating, 16 reviews

Luxury Lake Home! Dock Holidays Lake View Inn

The whole group will be comfortable in this spacious and unique space overlooking Lake Cumberland and Conley Bottom Marina. Luxury at its finest with a Beautiful Gourmet Kitchen, 4 Luxurious Master Bedrooms with their own Bathrooms, Bunkbed room and Queen Suite in the upper level. (Sleeps 20) Enjoy the 2 Large Patios with plenty of Lakeview seating! A 9 person Hot Tub and Sauna is also available on the lower level of the home. Note: Owners occupy separate lower level of home.

4.73 out of 5 average rating, 30 reviews

Cabin in Bronston

Tranquility Cabin

If you’re looking for somewhere you and your family can get away from all the noise and just enjoy nature, you’ve found it! Our cabin by the woods offers enough sleeping space for your whole family! Take a dip in the hottub after a day on the lake and enjoy a campfire after dark. We have a fully stocked kitchen as well as a Blackstone griddle on the deck. Distance to water: 1 mile to boat ramp 25 min. to Burnside Marina 35 min. to Lee’s Ford Marina 35 min. to Conley Bottom Marina

4.83 out of 5 average rating, 60 reviews

Barn in Corbin

Coyote Moon Ranch - Spacious 4 BR Barndo on Laurel

Create memories and enjoy the natural surroundings of the Daniel Boone Forest and Laurel Lake in Corbin, KY at Coyote Moon Ranch (CMR). Borders the Daniel Boone with trail access to Laurel Lake within a 5 minute hike. Bring your boat with access to Hightop Boat ramp within 1 mile of CMR. Enjoy the private 2 acre stocked fishing lake/dock during your stay. A unique western ranch right here in Kentucky! Escape the big city and experience the tranquility and nature of the outdoors!

5 out of 5 average rating, 11 reviews

Yurt in Corbin

The Honeymoon Hideaway

Escape to a romantic haven in the heart of Daniel Boone National Forest. Our cozy yurt features a queen bed, 2 rocking chairs, and a comfy couch, perfect for unwinding together. Outside, enjoy a private deck with a grill, fire pit, picnic table, and seating—ideal for intimate evenings under the stars. Nestled on our homestead, this peaceful retreat offers the perfect setting for a romantic getaway, where nature and serenity meet for unforgettable moments.

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Holiday House Rentals with a Kayak

Home in Pulaski County

Lakefront Woodson Bend 97-1

FrancesRating, 5 stars4 months ago

My family enjoyed our stay. Very peaceful and homie. Would definitely stay again.

4.89 out of 5 average rating, 9 reviews

Home in Campbellsville

HWY 55 Lakehouse

DavidRating, 5 stars9 months ago

Great location for my stay for a weekend fishing tournament. Easy to get go, close the ramp and the house was exactly how it’s described and clean. I’ll definitely book again for future pleasure trips to the lake!

5 out of 5 average rating, 7 reviews

Cumberland Belle Lakehouse-5bedrm,10bed,5bath

AdemRating, 5 stars1 week ago

The home was very clean, unique, and had an awesome vacation vibe. The hosts were very quick to answer questions and very accommodating. I would definitely recommend the home and plan on coming again!

Home in Somerset

5 out of 5 average rating, 12 reviews

Quirky Midcentury Bungalow close to everything!

RichardRating, 5 stars19 months ago

Wonderful place, great experience

Cumberland Belle Lakehouse 4bedrm, 10bed, 2.5bath

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Cabin rentals with a kayak

4.75 out of 5 average rating, 12 reviews

Cabin in Corbin

Coyote Moon Ranch - Cabin #1

LauraRating, 5 stars8 months ago

This was a great location to spend some family time together. Our kids loved the cabin and the short trip down the lake.

5 out of 5 average rating, 6 reviews

Cabin in Corbin

Coyote Moon Ranch - Cabin #6

EileenRating, 5 stars1 month ago

We loved our cabin. It worked out great for us. Got fish a little bit in the pond and caught a few small bass. The weather could have been better…but that’s Mother Nature’s fault. Will stay again for sure.