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.

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Top guest favourite
A modern living area is furnished with a comfortable gray sofa and an accent chair. A large flat-screen TV is mounted on the wall, while a decorative rug enhances the space. Natural light enters through the windows, illuminating the open layout.
Home in Anderson
4.98 out of 5 average rating, 114 reviews

Smart Condo Near Harrah's Casino

Looking for a place to stay that's smart, convenient, and near all the action? Look no further than this Airbnb! This condo is the perfect spot for those who want to be close to the casino, shopping, and everything in between Indianapolis and Muncie. And with all the amenities of home, you'll feel comfortable and relaxed during your stay. So why settle for a boring hotel room when you can have a smart and stylish condo all to yourself? Book your stay today and experience the best of both worlds!

Top guest favourite
A charming entrance features a covered porch with two white rocking chairs. Colorful flowers surround the pathway, leading to a welcoming front door adorned with a decorative welcome sign. A light fixture is positioned above the door, enhancing the entrance's appeal.
Home in Noblesville
4.98 out of 5 average rating, 179 reviews

The Cozy Cottage

Enjoy a relaxing getaway in this cozy cottage. Historic Downtown Noblesville is just a short walk where you will find great restaurants, pubs, and boutique shops. The cottage consists of one bedroom, a fully equipped kitchen, and a full bathroom with walk-in shower. There’s also a fenced backyard with fire pit and furniture. The Cozy Cottage is centrally located near downtown Noblesville (2 min), Ruoff Music Center (15 min), Grand Park Sporting Complex (20 min), and over 100 miles of trails.

Top guest favourite
The living area features a comfortable sofa and two wicker chairs, complemented by a coffee table on a soft area rug with leaf patterns. A Roku TV is positioned on a wooden console, while a decorative wall feature holds potted plants for a touch of nature.
Guest suite in Anderson
4.92 out of 5 average rating, 331 reviews

🦉Wooded Suite Retreat - 2BR Easy i69 Access!

Recharge surrounded by nature in this cozy, comfortable, clean 2 BR “in-law” suite nestled among towering ash trees in a rural, wooded neighborhood just outside town near the White River. Enjoy the full private apt (2 BR, LR, kitchen, bath, washer & dryer) on lower level of host’s home. Great for singles, couples, families or work travelers. Near I-69, Anderson University, Hoosier Park, Mounds State Park, Rangeline Nature Preserve, Anderson Airport, St Vincent & Community Hospitals & more!

Top guest favourite
A spacious bed is adorned with a patterned duvet and two decorative pillows. The headboard is neutral gray, and a piece of wall art is showcased above. A wooden bookshelf with decorative items is visible in the background, along with a bedside lamp.
Guest suite in Greenfield
4.96 out of 5 average rating, 164 reviews

Greenfield Garden Cottage-minutes from Indy

We are excited to offer our 3rd Airbnb listing, available now! You can check out our two other listings, Greenfield German Cottage and Greenfield Country Cottage. We have several years experience hosting through Airbnb and hundreds of happy guests. Our Garden Cottage offers plenty of space for 2 people to rest and relax. We offer a king size bed, large sitting area with tv, fridge and microwave. The grounds has gardens, water fountains, gazebo and wedding chapel for you to enjoy.

Guest favourite
The exterior of the property features a large covered porch with rustic wooden supports and a metal roof. A decorative horse statue stands prominently in front of a landscaped area with colorful flowers and gravel pathways, set against a backdrop of open fields and a blue sky.
Barn in Springport
4.97 out of 5 average rating, 37 reviews

Barndominium country retreat

Step into a stunningly unique taste of the West! This extraordinary property combines 40 gorgeous country acres with wooded trails, wildlife, horses and miniature cattle. Elegant western décor will assist you in slipping into vacation mode in no time. When you want to breathe in a bit of fresh air, bring your morning coffee or evening cocktail out to the furnished covered porch. This unforgettable getaway is perfect to simply escape the city and breathe the fresh country air.

Superhost
Cabin in Chesterfield
4.86 out of 5 average rating, 7 reviews

Muncie Cabin 2

ADA. Sleeps 4, 1Queen bed, 1 sleeper sofa queen size, Linens are included, full Bathroom including towels, kitchen with some utensils, full refrigerator and microwave, dinette table sits 4, heating and air conditioning, patio furniture, fire ring, and grill with filled propane to cook. 4 plates, 4 coffee cups, 1 coffee pot, 4 bowls, Pitcher w/ 4 cups, 2 blankets, 4 sheets, 4 pillows, 4 towels set (each set is 1 towel, 1 wash rag and 1 hand towel)

Top guest favourite
A spacious living area features warm wooden flooring and a cozy seating arrangement. A television is positioned on a dark wooden console, with a rocking chair nearby. A window seat with soft cushions offers additional seating, while framed photographs decorate the walls.
Apartment in Pendleton
4.98 out of 5 average rating, 352 reviews

Studio by Falls Park

Welcome to the Studio by Falls Park. This is a family-friendly studio apartment with a separate entrance. You are within walking distance to several good restaurants and the local drinking hole (The Wine Stable), Falls Park, walking trails. Located 10 minutes off I-69, and 20 minutes North of Indianapolis. Harrah’s casino is 15 minutes North on I-69. Studio has shower/bath, 1 queen bed, a full size futon, queen size blowup mattress and kitchen.

Top guest favourite
A spacious yard is framed by lush green grass under a colorful sky at sunset. Trees provide shade, while a vast field stretches into the distance, contributing to the peaceful ambiance of the serene surroundings.
Guest suite in Anderson
4.83 out of 5 average rating, 53 reviews

Quiet Country Retreat Near Casino

Skip the noise. Stay somewhere peaceful. Private suite just 7 min from Harrah’s Casino & I-69, Mounds State Park, and Anderson University. Quiet, family-friendly retreat with easy private parking. Unwind in the cozy 1-bed suite: comfy bed, sofa sleeper, smart TV, and fast Wi-Fi. A mini-fridge, microwave, and coffee maker. Perfect for couples or small families seeking peaceful nights and quick casino fun.

Guest favourite
A modern living room displays a sectional leather sofa arranged around a circular coffee table. A sleek fireplace is built into the wall beneath a large flat-screen television. Subtle lighting fixtures illuminate the space, complemented by decorative plants and artwork.
Home in Anderson
4.82 out of 5 average rating, 17 reviews

Family-Friendly Retreat

Escape to this peaceful, family-friendly retreat—where cozy meets spacious in a serene, stylish setting. Perfect for families or small groups, this beautifully designed home offers comfort, charm, and plenty of room to relax. Enjoy quiet mornings, stylish interiors, and a welcoming vibe that feels just like home. Ideal for making memories, unwinding, and experiencing a true sense of calm.

Top guest favourite
Guest suite in Muncie
4.96 out of 5 average rating, 124 reviews

Country Side Getaway l

Need a breathe of fresh air? Come enjoy this en suite in the country, over looking 10 acres of wetlands, fields, and forests. Take a dip in the pool or a walk in the woods and remember what it is like to live slow. En suite includes living room area with kitchenette, private bathroom, queen bed, and beautiful views of the countryside.

Top guest favourite
A spacious studio features a comfortable bed with a light-colored headboard, accompanied by a cozy seating area with a chair and couch. Natural light illuminates the room, and a decorative rug is placed on the floor. Wall-mounted lamps provide additional lighting.
Home in Pendleton
4.95 out of 5 average rating, 348 reviews

Studio M

Studio M is located in the small Historic town of Pendleton, IN. The home is within walking distance of our shops, restaurants and Falls Park. We have a fully stocked kitchen, car port with chairs to sit out and enjoy the beautiful outdoors. Our house is conveniently located to Fishers, Anderson, Noblesville and Indianapolis.

Top guest favourite
A spacious living area showcases a wooden coffee table and a cozy chair, complemented by a soft throw. Arched doorways lead to a dining area featuring a table and chairs. Natural light enhances the warm wood flooring and neutral wall colors.
Home in Muncie
4.97 out of 5 average rating, 301 reviews

Cozy One Bedroom Bungalow

Forget your worries in this spacious and serene space. This one bedroom bungalow is very close to Downtown, Ball State University and IU Health Ball Memorial Hospital. One block from a beautiful walking/bicycle riverwalk. Only minutes from local restaurants , coffee shops and breweries. Washer and dryer on site.

Popular amenities for Middletown vacation rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Henry County
  5. Middletown