Vacation rentals in Crestwood

4.82 out of 5 average rating, 44 reviews

An aerial view captures a spacious property with a refreshing pool surrounded by a white fence. The landscape is adorned with colorful autumn foliage, creating a serene atmosphere. A tranquil lake can be seen in the background, with the horizon lined by trees.

Home in Taylorsville

The Cozy Lake Place Cottage 75

Welcome to our tranquil Airbnb retreat, a charming cottage that accommodates up to 6 guests with 4 cozy beds. Nestled within a gated community, this getaway boasts lake views and a private hot tub for ultimate relaxation. You'll have access to a refreshing pool and playground at the resort. The surrounding woods offer a serene ambiance, while nearby hiking trails, fishing spots, and a marina with boat rentals, just a minute's drive away, ensure that adventure and leisure are always within reach.

Loft in Central Business District

A fully equipped kitchen features modern appliances, including a stainless steel refrigerator and a stove. A spacious island with bright yellow stools sits beneath pendant lighting. Exposed beams and a wooden floor complement the brick walls, while windows allow natural light to enhance the atmosphere.

4.93 out of 5 average rating, 91 reviews

Historic Nulu Loft| Downtown | Bourbon Trail

Our industrial loft is located in the historic Central Business District and NuLu area of Louisville. Local history mixes with a trendy and vibrant neighborhood known for its eclectic mix of art galleries, restaurants, and shops. The loft is situated close to all amenities and major attractions in downtown Louisville, including the popular Whiskey Row, Museum Row, Bourbon Trail and Louisville Slugger Field. We are a quick 12min drive to historic Churchill Downs, home of the Kentucky Derby.

4.84 out of 5 average rating, 89 reviews

A modern kitchen features sleek stainless steel appliances and a marble-topped island with seating for three. A textured brick wall adds character, while ample natural light fills the space through large windows, enhancing the contemporary design of this fully renovated area.

Home in Old Louisville

Exposition Center, Bourbon Trail, Downtown, & I65

Our guest will enjoy easy access to everything from this centrally located home. Right off of interstate 65. Conveniently located near downtown (2 miles), University of Louisville (1.1 miles), Cardinal Stadium (1.9 miles), Yum Center (2.3 miles), Churchill Downs (2.8 miles), Kentucky Exposition Center (3.1 miles), Louisville International Airport (3.9 miles), and many more local attractions. This home has been fully renovated and has two off street parking spaces in the rear of the house.

An aerial view of the two-story cottage reveals a spacious rear deck and well-maintained landscaping. The home is surrounded by lush greenery, with a gravel driveway leading to the entrance. Nearby, other cottages are visible along a winding path.

4.82 out of 5 average rating, 107 reviews

Lake Livin' & Bourbon Sippin'

Edgewater Resort, 20 minutes from Louisville, is Taylorsville Lake's premier vacation spot, tucked away in a gated community with over 163 acres that overlooks the marina. Within walking distance you'll find a community pool (seasonal) with a sand volleyball court and a fire pit. This two-story cottage sleeps up to 10 guests and showcases a master suite with two private balconies and a jetted soaking tub. You can also hang out on the private deck out back equipped with a 4-person hot tub.

4.89 out of 5 average rating, 122 reviews

Best view of the lake two bed two bath cottage #4

Make yourself at home in this cozy 2 bedroom 2 bath lakeside cottage with incredible views of Taylorsville Lake. You will love the open airy feel complete with deck and hot tub. Washer dryer, four beds that easily sleeps 7. TV in both the master bedroom and the living room. The wonderful community also offers a swimming pool and play area for kids. Enjoy the wildlife as well including deer and turkey as you explore the walking trails. We are located in the heart of the bourbon country!

4.73 out of 5 average rating, 165 reviews

Get Away From It All

GET AWAY FROM IT ALL at an idyllic cottage overlooking beautiful Taylorsville Lake. Quiet and tranquil in the fall and winter, lively and centrally situated for fun in the summer. Ideal for a weekend get away or a bluegrass adventure. Just minutes from Louisville and the famous Kentucky Bourbon Trail. Make this your headquarters for the Kentucky Derby, Bourbon tasting, hunting trips, or just to get away from it all. For larger parties, inquire about a joint rental with cottage #27!

Top guest favorite

A spacious living area features a comfortable gray sofa adorned with decorative cushions, positioned next to large windows offering expansive water views. A glass coffee table rests on tiled flooring, surrounded by light-colored decor accents. Natural light fills the space, enhancing the serene atmosphere.

Home in Louisville

4.95 out of 5 average rating, 171 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Cottage in Spencer County

Aerial view captures Taylorsville Lake, surrounded by lush greenery and autumn foliage. The winding shoreline is visible alongside the marina with several boat docks. The community road runs beside the scenic landscape, providing a clear view of the serene water and rolling hills.

4.91 out of 5 average rating, 151 reviews

Peaceful Cottage Minutes from Lake Access

Welcome to our fully stocked getaway! In this 2 bed, 2 bath cottage you will find everything you need to have a relaxing and fun vacation. You will love the deck with scenic views of Taylorsville Lake, and a hot tub with privacy fence. Lake access is less than a 5 minute drive, and there is a community pool just down the road when in season, and other community amenities you can enjoy. We are excited to host you here and hope that you will enjoy this place as much as we have!

4.92 out of 5 average rating, 106 reviews

The image shows a hot tub on a covered deck, with bubbling water and a view of a backyard fire pit area below. Four blue Adirondack chairs surround the fire pit, which is under a canopy of string lights amidst lush greenery.

Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

4.94 out of 5 average rating, 66 reviews

Home in Shelbyville

B on the Bourbon Trail with pub, pool and hot tub

Discover Kentucky's Finest - B on the Bourbon Trail. With a saltwater pool, hot tub, fire pit, and Pub B, this historic colonial estate on 3 acres is near over 30 renowned distilleries, 35 minutes from the iconic Churchill Downs, and just an hour away from the prestigious Keeneland racecourse, B On The Bourbon Trail offers unparalleled access to Kentucky's most treasured attractions and promises an unforgettable experience in the heart of Kentucky's bourbon country.

Top guest favorite

An outdoor deck features a stone fire pit surrounded by comfortable seating. Two wicker chairs, adorned with decorative cushions, face the serene view of the landscape. Clear skies and rolling hills create a tranquil backdrop, ideal for relaxation.