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Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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

Superhost

Home in Taylorsville

4.83 out of 5 average rating, 36 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.

Superhost

Home in Louisville

4.73 out of 5 average rating, 15 reviews

Calm Serene Studio Getaway Louisville by Expo Ctr

Welcome to your next charming getaway in Louisville Ky. Attached studio style unit to a home. Close to the airport you will be home shortly after landing. Treat yourself to a quiet stay with everything you need. Big screen TV with a comfortable couch. Relax & unwind in premium bedding. Private entrance from the back of the house with your own deck area for a comforting time sitting outside. Washer and Dryer in unit for longer stays. Close to groceries, shopping centers, parks, and expo center.

Guest favorite

Chalet in Borden

4.98 out of 5 average rating, 65 reviews

Top of the Rock

This isn't a vacation rental...it's an ADVENTURE! Escape to an exhilarating hilltop haven on Top of the Rock, a captivating chalet resting 800 feet above sea-level that beckons you into a private paradise of farmland and forest. The triple balcony unveils breathtaking views of stunning Star Valley, nestled in the famed knobs of Southern Indiana. Inside, discover a spacious blend of rustic & cozy: a grand Great Room with a 30-foot ceiling, diverse common spaces, and comfortable sleeping for 10.

Superhost

Home in Old Louisville

4.84 out of 5 average rating, 81 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.

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 favorite

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 favorite

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 favorite

Cottage in Taylorsville

4.96 out of 5 average rating, 189 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 favorite

Cabin in Mount Eden

4.98 out of 5 average rating, 136 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 favorite

Home in New Albany

4.95 out of 5 average rating, 125 reviews

King bed and oasis backyard with hot tub, firepit

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!

Guest favorite

Home in Jeffersonville

4.99 out of 5 average rating, 71 reviews

Beachfront River Cottage

Brand New to Market! June 2023. Escape to our Beachfront River Cottage for tranquility and breathtaking panoramic river views. This charming retreat features an AC/Heated porch, fully stocked kitchen, riverside deck, and a private beach. Only 7 mins to Garrett's General Store in downtown Utica, 17 mins to downtown Jeffersonville, 20 mins to downtown Louisville, and 29 mins to Churchill Downs, home of the Kentucky Derby!

Superhost

Home in Taylorsville

4.85 out of 5 average rating, 68 reviews

3 Bed / 3 bath cottage NEW Hot Tub

Welcome to this awesome house in this gated community overlooking Taylorsville Lake. Huge Community Pool, sand volleyball & basketball hoop. Large open floor plan with fully stocked kitchen and living room. Huge master bedroom with private deck and whirlpool bathtub. Boat rentals available at the marina seconds away. Kayak and Canoe Rentals nearby. 25 minute scenic drive to Louisville Welcome to Edgewater Resort

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middletown vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Middletown's top sights

Havana Rumba Middletown32 locals recommend
Main Event Louisville31 locals recommend
Mark's Feed Store29 locals recommend
The Village Anchor24 locals recommend
Xscape Theater Blankenbaker 1422 locals recommend
The Fresh Market13 locals recommend

Other great vacation rentals in Middletown

Superhost

Vacation home in Louisville

4.77 out of 5 average rating, 30 reviews

Historical Mansion 7BD Vacation Home in Derby City

Guest favorite

Home in Shelbyville

5 out of 5 average rating, 22 reviews

Bourbon by the Lake

Guest favorite

Home in Elizabeth

4.98 out of 5 average rating, 125 reviews

Cabin on Lake Close to Louisville Ky

Guest favorite

Apartment in Central Business District

5 out of 5 average rating, 80 reviews

Modern Luxury Apt: King Bed, Coffee Bar, Hot Tub!

Guest favorite

Apartment in Louisville

4.83 out of 5 average rating, 120 reviews

Highlands Harmony House - Near Cherokee Park

Guest favorite

Farm stay in Simpsonville

4.9 out of 5 average rating, 60 reviews

Spacious Home with Beautiful Views

Guest favorite

Condo in Highlands

4.94 out of 5 average rating, 186 reviews

Large Townhouse, Walk to All! King beds, 2.5 baths

Guest favorite

Home in Louisville

5 out of 5 average rating, 15 reviews

Bourbon Country Cottage

Show all

Quick stats about vacation rentals in Middletown

  • Total rentals

    50 properties

  • Nightly prices starting at

    G$10,446 GYD before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Frequently Asked Questions

  • Do house rentals in Middletown have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Middletown?

    Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 20 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Middletown?

    Middletown has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Middletown have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Middletown?

    Experience the best of Middletown with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Middletown have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middletown have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Jefferson County
  5. Middletown