Waterfront vacation rentals in Jessamine County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Jessamine County

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

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Guest favorite

Cottage in Wilmore

4.98 out of 5 average rating, 168 reviews

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

Guest favorite

Cabin in Lexington

4.85 out of 5 average rating, 208 reviews

Rural Kentucky River Palisades Cabin/Past Distilry

Fabulous Cabin & Views of Kentucky River Palisades;Rural Escape 20 minutes S of Lexington;Scenic & Treasured Landscape.View wildlife,Rock Formations,Fall Colors.One mile riverfront,boat ramp&fishing lake;Kayaks&Pontoon Boat avail(xtra fee)Hike & explore 57 acres. History abounds:Site of 1860 Bourbon Distillery;Daniel Boone lived & surveyed from Boone’s Knoll;Loretta Lynn&Dolly Parton performed here;Camp Nelson Civil War National Landmark adjacent;Paul Sawyier’s chosen spot for plein air painting

Home in Harrodsburg

New place to stay

The Blue Heron Lakeside Chalet

Welcome to The Blue Heron Chalet, where tranquility meets breathtaking views on the shores of Herrington Lake. Our charming A-frame invites you to unwind in the serene beauty of Kentucky. Whether you're seeking a romantic retreat, a family vacation, or a gathering of friends, our lakeside chalet promises an unforgettable experience filled with relaxation, adventure, and cherished memories. Welcome to your home away from home in the heart of the Bluegrass and minutes away from the Bourbon Trail

Home in Lancaster

New place to stay

Lake side Bluff at Sunset Marina

Herrington Lake! Beautiful home located next to Sunset Marina and Resort at Herrington Lake. Located minutes from Kennedy Bridge on the Lancaster Kentucky side of Herrington Lake. Outstanding lake view with a parklike setting close to Marinas and Restaurants. Home is fully appointed with all you need for a comfortable retreat! Spend the day on the lake and relax on the deck and watch the boats go by. Located in a no wake zone and only minutes from local marinas and nearby towns. Well Kept!

Guest favorite

Vacation home in Nicholasville

5.0 out of 5 average rating, 5 reviews

Stone & Cedar Lodge - pool, hot tub, campfire, EV

Relax with the whole family at this peaceful country ranch in the heart of the Bluegrass. Sleeps 16 - 5 Bedrooms, 8 Beds, 3 Baths Located just outside of Lexington and only 12 miles from Keeneland. New 7 seat hot tub. The solar heated pool is open from April until September. The tree house, swings and trampoline are big hit. Play a game of pool, basketball or corn hole. Enjoy quiet walks around the pond or roast marshmallows around a cozy campfire. Wheelchair access Level 2 EV charger.

Guest favorite

Home in Lancaster

4.94 out of 5 average rating, 35 reviews

Luxury Lake House with must see view

This 3791sqft home on Herrington Lake is a new rental with brand new furnishings throughout as of May 2023. You'll see the lake as soon as you pull into the drive, the view is simply breathtaking. With a large driveway and additional large parking pad complete with electrical outlets for electric cars there is plenty of parking so bring your boat/jet skis. Don't have a boat? There are 4 nearby marinas that offer boat rentals, dining, and activities. The closest is only 3 minutes away!

Guest favorite

Home in Lexington

5.0 out of 5 average rating, 17 reviews

Woodsy Cabin in City, King bed. Walk in shower

Unwind at this Creekside cabin. It's the perfect fusion of city convenience with nature vibes. The backyard is lined with native shrubs, creek and abundant hardwoods. Listen to the birds on the spacious deck. Walk to the park. UK, Keeneland and the Airport are only approx 10min. Great shopping and restaurants within a few miles. The large King size bedroom with private bath has walk in shower and opens to the private wooded deck. High end quality Pima cotton sheets. Roku TV. Edit

Home in Harrodsburg

4.73 out of 5 average rating, 30 reviews

Rare scenic KY River home with private boat ramp

Welcome to The River House at The Village at Palisades! Relax or explore with family and friends at this peaceful home away from the busy, inner-city life, but only a short 25-minute drive to Lexington. Separate living spaces for adults and children if desired. Games are provided in the game room for hours of fun! The Village at Palisades has one of the only boat ramps that provide convenient access to the Kentucky River for fishing, Kayaking, (ect.) and is only open for our guests.

Guest favorite

Home in Lancaster

4.98 out of 5 average rating, 60 reviews

‘Our Lakeside Retreat’ w/ Deck on Lake Herrington!

Sitting on the shores of Lake Herrington, this Lancaster vacation rental is a haven for fishermen and those seeking sunny days on the water! The 3-bedroom, 1.5-bath home is complete with a gas stone fireplace, fully equipped kitchen, and a furnished deck that offers waterfront views. Spend mornings lounging on one of the deck's chaises before heading out to explore the Old Fort Harrod State Park. End the day with a cookout on the gas grill and a movie night in the family room!

Guest favorite

Home in Harrodsburg

5.0 out of 5 average rating, 17 reviews

The River Side Lodge- with private boat dock!

Welcome to The River Side Lodge at the Palisades! Relax and fish by the the river on your own private dock, roast marshmallows by the fire, play in our game room, grill out over looking the beautiful view, or just cuddle up on the couch Netflix and chill 😎 This property offers fun for the whole family, or a sweet get away for couples. While this area is a quiet little getaway surrounded by nature, it is only a 25 minute drive from Lexington and 15 minutes from Nicholasville!

Guest favorite

Home in Lancaster

4.85 out of 5 average rating, 27 reviews

Lakefront property - Higher Ground

Welcome to our stunning lakeside retreat on Herrington Lake! Nestled amidst serene surroundings, our property offers the perfect getaway for guests seeking relaxation and adventure. With 6 bedrooms, 3 bathrooms, and sleeping accommodations for up to 14 guests, there's ample space for families and friends to unwind and create lasting memories. Recently renovated in 2022, our home boasts modern amenities and stylish decor, ensuring a comfortable and enjoyable stay for all.

Guest favorite

Home in Harrodsburg

4.95 out of 5 average rating, 38 reviews

Lux Lake Gem w/ hot tub

Welcome to luxury lake life living situated on the best part of the 3,600 acre Herrington Lake. This low traffic, dead end street is located short distance from Pandora Marina, and a few minutes drive to Chimney Rock Marina and Kennedy Bridge Marina. With tons of patio space directly facing the lake, you’ll be sure to enjoy the view in or out of the hot tub. Boat rental available during season!