Holiday rentals with a kayak in Lake Cumberland

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Top-rated Accommodation with a Kayak in Lake Cumberland

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Superhost

Home in Monticello

5 out of 5 average rating, 5 reviews

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

Perfect space for your get together or event! 5 Bedrooms, 5 Attached Baths, 10 Beds. Sleeps 20 easily. New SwimSpa (large hot tub/ small lap pool)! Entire 2nd floor unit. 2 large decks. Plenty of parking. 2 gas grills and a fire pit. Must be comfortable with STAIRS as this is a second floor unit. ***There is a separate listing to rent the entire home if more space is needed. This would add 4 additional bedrooms (10 beds) 2 more bathrooms, a full kitchen, dining table for 20 and access to sauna

Guest favourite

Tiny home in Monticello

4.94 out of 5 average rating, 217 reviews

*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.

Home in Somerset

5 out of 5 average rating, 12 reviews

Quirky Midcentury Bungalow close to everything!

This centrally-located midcentury bungalow sits on almost an acre with two bedrooms and a jack and jill bath. The closest boat ramp is just a third of a mile away and there are 5 total boat ramps within 5 miles. The house sits right off 27 and is minutes away from several restaurants and popular Lake destinations. We are just 2 miles to Burnside Marina with a boat ramp and golfing. Come experience Lake Cumberland and be next to everything you want! We look forward to sharing our home with you.

Top Guest favourite

Cabin in Russell Springs

5 out of 5 average rating, 23 reviews

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!

Guest favourite

Home in Jamestown

4.84 out of 5 average rating, 25 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.

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!

Top Guest favourite

Home in Monticello

5 out of 5 average rating, 18 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.

Top Guest favourite

Farm stay in Somerset

4.98 out of 5 average rating, 61 reviews

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!

Guest favourite

Home in Campbellsville

4.89 out of 5 average rating, 9 reviews

HWY 55 Lakehouse

This home sleeps 8 comfortably fully equipped with all the comforts of home. It's conveniently located off HWY 55 South between the cities of Columbia and Campbellsville only minutes from the Green River and Green River Lake. There's 2 spacious bedrooms, a full bath, laundry room, living room, eat-in large kitchen. The backyard has a patio and 4 camping sites with full hook-ups. Campers are welcome for an extra fee. There's plenty of parking for boats along with charging stations.

Top Guest favourite

Home in Monticello

5 out of 5 average rating, 14 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.

Superhost

Cabin in Bronston

4.72 out of 5 average rating, 29 reviews

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

Yurt in Corbin

5 out of 5 average rating, 3 reviews

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.