Vacation rentals in Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middletown

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

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Guest favourite

Home in Taylorsville

4.84 out of 5 average rating, 38 reviews

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.

Guest favourite

Cottage in Bardstown

4.98 out of 5 average rating, 396 reviews

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

Superhost

Home in Old Louisville

4.84 out of 5 average rating, 82 reviews

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.

Guest favourite

Loft in Central Business District

4.96 out of 5 average rating, 84 reviews

NuLu Loft 1885|Historic|Free Parking| KY Derby

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

Superhost

Cottage in Taylorsville

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.

Guest favourite

Cottage in Taylorsville

4.89 out of 5 average rating, 121 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!

Guest favourite

Cottage in Spencer County

4.91 out of 5 average rating, 150 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!

Guest favourite

Home in La Grange

4.95 out of 5 average rating, 99 reviews

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.

Guest favourite

Cottage in Taylorsville

4.96 out of 5 average rating, 190 reviews

Four Seasons Cottage at Taylorsville Lake KY

Nestled in the Bourbon Trail hills of Kentucky, rests Taylorsville Lakes only waterfront vacation community. Strategically placed; Cottage 37 sits on a ridge that overlooks the 3,050-acre lake and its 10,000 acres of wildlife preserve. The owners tried to capture the view from the kitchen table to inspire the cabins four-season theme. The wall hangings were chosen to mirror Kentucky’s beautiful hills, Derby culture, and the water of Taylorsville Lake.

Guest favourite

Cabin in Mount Eden

4.98 out of 5 average rating, 137 reviews

Bourbon Country Cottage

Newly renovated cottage located in the country. Enjoy amazing views from the porch while enjoying the outdoor patio. Fully furnished to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a well equipped kitchen for cooking. Enjoy exploring the walking trails, creek and the 80 acre property while you stay. Stocked Fishing Pond Check out our other listing too, Bourbon Country Cabin, same property.

Guest favourite

Home in Bardstown

4.92 out of 5 average rating, 138 reviews

McIntyre’s Country Getaway

If you're looking to stay somewhere in the country that feels like home this is it! This getaway is nestled in the outskirts of the bourbon capital. We are conveniently located 6 miles from downtown Bardstown where you can find shopping, dining and nightlife. We also located next door to McIntyre & Family Winery. During your stay make sure to check out the tasting room there!! This house also has washer and dryer available

Guest favourite

Home in New Albany

4.95 out of 5 average rating, 129 reviews

DERBY king bed and oasis backyard with hot tub

11 miles to Derby. Come enjoy our newly decorated house with a hot tub, gazebo outdoor fun area and lounge furniture and wood burning fire pit. The idea is to both indoor and outdoor give you a great experience that not everyone offers! We sleep 4 adults comfortably in our 1 KING size bedroom and 1 QUEEN size bedroom. We're located in a quiet neighborhood with a fully fenced in backyard and we're Pet Friendly with a fee!