
Holiday rentals in Middletown
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Top-rated holiday rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness and more.

Harmony Hideaway, 5 min to BSU, Summer Pool, Games
Discover your spacious retreat (over 4000 sf) with a refreshing heated pool (summertime) and games. This inviting home sleeps 19 people (17 adults and 2 infant/toddler) and includes six bedrooms with seven queen-size beds, one king-size bed, one twin bed, one toddler bed & one crib. With a fenced backyard and a two-car garage, it is a blend of comfort & versatility. Book now for a memorable stay! Conveniently located near main roads and shopping, with a 5-minute drive to the BSU and IU Hospital.

Greenfield German Cottage-minutes to downtown Indy
The perfect place for you to stay when visiting Greenfield or nearby Indianapolis. Located within 1/2 mile of I-70. Restaurants and shopping within 1 mile. Downtown Indy is an easy 20-mile drive. We offer a comfy queen size bed, comfy roll away twin bed, kitchenette, full bathroom, walk-in closet, sitting area with couch and tv, private entrance with a private drive and parking area. You can also enjoy many extra features on the property, which include beautiful flower gardens and fountains.

Spacious 3 Bedroom Home - New Castle
This home is equipped with everything you need for a relaxing stay. Unwind in the living room while watching your 65” TV. Prepare a meal in the fully equipped kitchen. The home offers a King, Full, and 2 Twin size beds. All 3 bedrooms are fitted with room darkening curtains. If you need a quick start, grab a shot of espresso on the way out the door. For a slow morning, pour yourself a cup of coffee and relax on the large back deck. The fully equipped laundry area offers washer, dryer, and iron.

The Eagles Nest, two bedroom retreat.
Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Maxwell-Commons #105, New Castle IN, 2bd2bth dwntn
#105 Maxwell-Commons: downtown LOFT for business, family, pleasure - HAVEN for peace. Wild party? PLEASE go elsewhere. Nea: HC Saddle Club; Go-Karts; NC High School; Hall of Fame. Indianapolis 50min; Richmond 30min; Muncie, Anderson 20min. Bring toiletries. Coffee available. THERE ARE STAIRS. 3 or 100s of guest voiced complaint re overnight trains. I am powerless over the midwest rail-schedules. It is fair to let would-be guests know. There are 2 assigned outdoor parking-spaces.

🦉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!

The Milton Manor/ near BSU/Minnitrista
Come stay at this fun retreat and enjoy shopping and restaurants in any direction you go. This home is located across from the Delaware County Fair grounds in a very quiet neighborhood centrally located in Muncie sitting very close to Ball State University and IU Hospital and if you like to bike ride, Cardinal Greenway bike trail is very close by. Enjoy the many games provided for all age groups along with some grilling out , corn hole games and enjoy some hot tub time under the stars.

Cozy place next to Cardinal Greenway
Enjoy your stay in Muncie in a spacious two bedroom, one and a half bath. This property is located in a safe and quiet residential neighborhood making it an ideal home for anyone looking for a comfortable place to stay. This home is in a quaint country setting and offers a great amount of space with a large backyard and driveway. Only a 10-minute drive to BSU and IU Health Ball Memorial Hospital. Direct access to the Cardinal Greenway from the backyard.

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.

Private, one car garage, hot coffee
Welcome to Robin's Nest, my cozy, modern, open-concept home in Indy! This inviting space includes 2 bedrooms, 1 bathroom, and 2 queen beds. Enjoy amenities such as a coffee bar, fire pit, and workstation. Let your fur babies run free in my fully fenced-in yard. You’re in close proximity to Lucas Oil, the Convention Center, and Gainbridge Fieldhouse, Murat, and many major hospitals are in a 10 mile radius.

The Duchess-- Boutique Guest House
Beautifully restored house in the historical district near downtown Anderson. 5-10 walk to downtown restaurants, bars and art museum. 5-10 minute drive to grocery stores and shopping center. Newly furnished and decorated just for Airbnb guests. Fully stocked kitchen, fast Wifi and washer/dryer good for long stays or just a weekend away for relaxing. I'll be less than 5 minutes away for any help you need.

Cumberland Cottage
The Cumberland Cottage is ideal for couples, families, or groups of friends exploring the area. Featuring cozy accommodations and a prime location, visitors are guaranteed a delightful experience. The property sits right next to a lovely church, and while it is situated in the city close to various amenities, it uses well water, making it suitable for those sensitive to municipal water.
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown

South Campus

The Cabin

Spacious home near BSU & IU.

Riverfront Noblesville Home/Pet Friendly/kayaks!

The Clematis Cottage- Hot tub

Registered historic home, heart of Muncie

Hickory Hill Estates Carriage House (Muncie)

Carriage house on 13+ acre gated estate property!
Destinations to explore
- Chicago Holiday rentals
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- Lucas Oil Stadium
- Indianapolis Motor Speedway
- Indiana Convention Center
- Eagle Creek Park
- Indianapolis Zoo
- Gainbridge Fieldhouse
- Brickyard Crossing
- Indiana State Fairgrounds & Event Center
- Grand Park Sports Campus
- Indianapolis Museum of Art
- Childrens Museum
- Ball State University
- Garfield Park
- Indiana State Museum
- Indiana World War Memorial
- Indianapolis Canal Walk
- White River State Park
- IUPUI Campus Center
- Butler University
- Fort Harrison State Park
- Victory Field
- Circle Centre Mall Shopping Center
- University of Indianapolis
- Holliday Park




