
Vacation rentals with outdoor seating in Middletown
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Top-rated outdoor seating rentals in Middletown
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Chic Cabin w/ Trails, Hot Tub & Starry Nights
Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

RIView 103. Modern Waterfront Suite Kentucky Derby
Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Home near the Highways
Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

Captain's Cabin: Bourbon Trail, History & Romance
Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Historic Cabin by Bourbon Trail
Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Private EAST END gem, minutes to everything!
Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

502 House @ Progress Park w/ Game Room
Welcome to Progress Park! A true getaway for fun! Located on a 12 acre Airstream Glamping resort w/ a 2 acre swimming pond. Sleeps 8 comfortably in the beds with 2 leather futons. Enjoy all the luxuries of home w/ added amenities such as a custom game room & luxurious backyard with TV, firepit & grill. Relax, unplug and reconnect in our little slice of heaven. Progress Park has 8 total units on site. 2 houses, 5 airstreams & a bunk house. *DERBY IS A MIN THURS-SUN REQUIRED

Private Prospect Flat
Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

The City Cottage…quiet, peaceful, and convenient!
A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Olive Branch Suite with projector screen in E Lou
This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

My Old Kentucky Dome
An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Newly Updated: Spacious Suite/Private Entry
My guest suite is close to restaurants, business parks, shopping and easy access to highways. Guests love this place because of the big trees, green space and private entrance. The patio is great for sipping morning coffee, reading or enjoying an evening beverage. Beautiful, quiet neighborhood is perfect for a walk/run. This spacious, comfortable suite is good for couples, solo adventurers, business travelers and small families.
Popular amenities for Middletown outdoor seating rentals
House rentals with outdoor seating

Butchertown & NuLu's Shantyboathouse

Romance country getaway with hot tub

2 br home, walking distance to much entertainment

Atoka Farms

Quaint Highland's Bungalow

The Jungalow: 65" 4K TV, memory foam, kid-friendly

Bourbon Trail Spacious Backyard NEW HotTub Grill!

Best Location in the City-2 Story Patio & Hot Tub
Apartment rentals with outdoor seating

★ Victorian Louisville ★ Beautiful 1200 sqft Apt

Urban Bourbon Farm Loft

Lucky Horseshoe

Apartment on Frankfort Ave: Walkout Basement

Deuward’s Den - In Historic Corydon, IN

Downtown Luxury 1BR Apt near Louisville KY

Haus on Speed, charming 2nd floor apartment

Renovated Riverfront Apartment with Elevated Deck
Condo rentals with outdoor seating

Luxury 1-Bed Oasis In Heart Of Highlands W/ Free P

Hidden GEM, newly furnished in a safe, great area

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace

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

Spacious Riverfront Condo Minutes from Downtown!

Downtown Condo | Private 1 CAR Garage & Balcony

Charming Penthouse/Rooftop Patio/Downtown

BEST View of Louisville
Quick stats about vacation rentals with outdoor seating in Middletown
Total rentals
20 properties
Nightly prices starting at
R1,390 ZAR before taxes and fees
Total number of reviews
630 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Rentals with a patio Middletown
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- Rentals with outdoor seating Jefferson County
- Rentals with outdoor seating Kentucky
- Rentals with outdoor seating United States
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Valhalla Golf Club
- Muhammad Ali Center
- Angel's Envy Distillery
- Louisville Slugger Field
- Louisville Slugger Museum & Factory
- Turtle Run Winery
- Heritage Hill Golf Club
- Anderson Dean Community Park
- Charlestown State Park
- Waterfront Park
- Kentucky Science Center
- Falls of the Ohio State Park
- Big Four Bridge
- River Run Family Water Park
- Frazier History Museum
- Evan Williams Bourbon Experience
- Big Spring Country Club
- Rising Sons Home Farm Winery
- Bruners Farm and Winery
- Best Vineyards
- Wildside Winery