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.

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Top guest favourite
The backyard features a circular pool surrounded by a spacious concrete patio. A wooden deck is accessible from the upper level, and lounge chairs are positioned nearby. Lush landscaping and a hammock complete the inviting outdoor space, creating an enjoyable area for relaxation.
Home in Halteman
4.91 out of 5 average rating, 100 reviews

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.

Top guest favourite
A cozy sleeping area features a queen-sized bed dressed in a decorative quilt with accent pillows. A floral painting adorns the wall above the bed, while a bedside lamp provides soft lighting. Drapes frame the window, allowing natural light to filter in.
Guest suite in Greenfield
4.94 out of 5 average rating, 262 reviews

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.

Guest favourite
A living room features a comfortable gray sofa adorned with orange and white pillows. A dark coffee table is centered, surrounded by a patterned area rug. A large TV is mounted on the wall, and two windows with room darkening curtains allow natural light to enter. A plant in the corner adds a touch of greenery.
Home in New Castle
4.97 out of 5 average rating, 183 reviews

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.

Top guest favourite
A serene bedroom features a spacious bed with soft linens and decorative pillows. A reading chair is positioned next to large windows, allowing natural light to illuminate the room. A decorative sign and plants add subtle character to the calming atmosphere.
Guest suite in Muncie
4.97 out of 5 average rating, 412 reviews

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!

Top guest favourite
An open living area is presented with high ceilings and exposed beams. A comfortable gray sofa faces a wall-mounted television, while a dining table is positioned beside a fully equipped kitchen. Large windows allow natural light to illuminate the space, enhancing the inviting atmosphere.
Apartment in New Castle
4.96 out of 5 average rating, 210 reviews

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.

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, 318 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 welcoming wooden deck is accessible via a gentle ramp, surrounded by lush greenery and colorful plants. A circular table with chairs is positioned on the deck, providing an inviting space for outdoor gatherings. The front of the house features large windows allowing natural light.
Home in Muncie
4.97 out of 5 average rating, 245 reviews

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.

Top guest favourite
The living room features a light-colored couch adorned with red pillows, facing a wooden coffee table. A large piece of wall art depicting a tree is displayed above the couch. Natural light enters through sliding glass doors, complemented by two lamps positioned beside the couch.
Home in Muncie
4.93 out of 5 average rating, 120 reviews

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.

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.
Flat in Pendleton
4.98 out of 5 average rating, 332 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.

Guest favourite
A modern living area is highlighted by a comfortable sectional sofa adorned with decorative pillows. A pair of armchairs and a wooden coffee table create a cozy seating arrangement. Natural light filters in through the window, complemented by a stylish lamp and wall art.
Home in Indianapolis
4.95 out of 5 average rating, 174 reviews

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.

Guest favourite
A cozy bedroom features a spacious white bed adorned with decorative pillows. Dark blue walls are complemented by framed art pieces above, adding a touch of elegance. A wooden floor creates a contrasting warm element, enhancing the room's overall design.
Apartment in Anderson
4.89 out of 5 average rating, 116 reviews

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.

Guest favourite
A single-story stone house is set on a spacious lot with a paved driveway leading to a two-car garage. Surrounding trees are seen in the background, and a white fence borders the property. The sky features scattered clouds and a bright blue hue.
Home in Noblesville
4.87 out of 5 average rating, 127 reviews

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

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