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
A cozy living area is highlighted by a three-bulb brass chandelier above a tan sofa, complemented by a wooden table. The wall features an arrangement of framed mirrors in gold and silver tones, while a doorway leads to other areas of the carriage house.
Guest house in Meridian Kessler
4.99 out of 5 average rating, 255 reviews

Charming Meridian Kessler Carriage House

Second floor carriage house in historic Indianapolis neighborhood. Renovated and with original architectural details like the hardwood floors. This cozy space is perfect for one or two people looking for a convenient midtown Indy location. Safe walkable neighborhood close to many restaurants. We've made the space a beautiful home away from home - lovely linens, fiber wifi and an excellent coffee machine. Like our space, but aren't coming to Indy? Message and we'll send you the shopping link.

Guest favourite
An inviting recreational space features a classic arcade setup alongside a popcorn movie bar. A cozy seating area is arranged with a smart TV and electric fireplace. A claw soaking tub is visible, complemented by a private hot tub, promoting relaxation and fun for guests.
Home in Greensboro
4.87 out of 5 average rating, 122 reviews

Hot Tub Arcadia - Relax and Play

Designed with couples in mind, where relaxation and entertainment await! You'll enjoy the serenity of a small-town country getaway. Features: •Hot Tub •Arcade •Popcorn Movie Bar •Board Games •Claw Tub •King bed •Workspace with vanity. •Twin bunk bed •Murphy Bed for 5th guest •Fully equipped kitchen •Outdoor patio with seating for two and completely private hot tub. •Wi-Fi and smart TV •Washer/dryer Ideal for: • Couples seeking a romantic getaway • Small families looking for a relaxing vacation

Top guest favourite
A spacious living room features two dark blue sofas facing each other, centered around a wooden coffee table. A large flat-screen TV is mounted on the wall above an electric fireplace. Soft lighting from lamps accentuates the cozy atmosphere, complemented by a colorful area rug.
Home in Muncie
4.96 out of 5 average rating, 103 reviews

Farm Themed w/2 Game Rooms & HOT TUB -2 min to BSU

Come and enjoy our newly renovated Tri-Level "Farmhouse" Home! -Large and relaxing Hot tub, with ample outdoor seating, fully fenced in back yard -3 KING beds, and 2 Twins between 4 bedrooms Lots of activities-Pool table, Chess table, Golden Tee Classic, Mrs. Pacman, Ping Pong, Foosball, and board games -Accommodates up to 8 people - Children and pet friendly -Located in a quiet, safe neighborhood - 4 min to Ball State, 7 Min to Downtown Muncie -Roku Smart TV's in each room Relax, and have fun!

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, 266 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.

Top guest favourite
Home in Muncie
4.93 out of 5 average rating, 123 reviews

Cozy place next to Cardinal Greenway

Enjoy your stay in Muncie in a spacious two bedroom, one and a half bath right next to a peaceful walking trail. 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.

Guest favourite
A charming historic home with a two-story structure displays a combination of deep purple and mustard yellow siding. An American flag hangs from the porch, which features decorative woodwork and inviting entry steps surrounded by landscaped gardens.
Home in Greenfield
4.94 out of 5 average rating, 123 reviews

Updated Historic Home, in the Heart of Greenfield

A one-of-a-kind historic gem located three blocks from Downtown Greenfield on Main Street and only a 35-minute drive to downtown Indianapolis. Enjoy the entire downstairs of this completely upgraded late 1800's wooden frame home featuring all original wood flooring and beautiful antique furniture pieces. Filled with modern luxuries; including 3 flat screen tv's with streaming services included, an upgraded 8 burner gas stove, dishwasher, full-size washer and dryer, and outdoor barbecue grill.

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, 211 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.

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

šŸ¦‰Wooded Suite Retreat - 2BR Easy i69 Access!

Recharge surrounded by nature in this cozy, comfortable, clean 2 BR ā€œin-lawā€ 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!

Guest favourite
A cozy living room features a dark couch adorned with decorative cushions, paired with a patterned loveseat. A coffee table sits at the center, with two cups resting atop it. Natural light enters through two windows, framed by soft curtains, illuminating the wooden floor.
Flat in Old West End
4.91 out of 5 average rating, 193 reviews

Central Location. Very comfy & clean with view.

This lovely little retreat will not disappoint. I think you will find it to be a relaxing and comfortable place to spend your time in Muncie. We've provided the basics so that it can be your home away from home: fully functioning kitchen, coffee options, hi speed internet, towels, shampoo, conditioner, soaps, bedding, xfinity flex with tv, and board games. 1/2 mile to shops & dining or a walk along the river, 1 mile to BSU. Close the day grilling out while you watch the gorgeous sunset.

Guest favourite
A stone fire pit constructed in a circular shape is positioned on the grassy area. Nearby, a large deck overlooks a serene river, surrounded by lush trees. Two bright red chairs complement the outdoor setting, providing seating to enjoy the natural views.
Cottage in Noblesville
4.97 out of 5 average rating, 206 reviews

Quiet Riverfront Escape/Kayaks/Pet Friendly/Views!

Welcome to @WhiteRiverCasita - a cozy getaway minutes from historic downtown Noblesville and Koteewi Park - enjoy a breathtaking slide down Koteewi Run, Indianapolis’ best and only snow tubing hill! This hidden 1-bedroom, 1-bath gem features a large deck overlooking the river with comfortable furniture for dining and enjoying the outdoors. You’ll love the peaceful surroundings but there’s also plenty to do nearby, including kayaking, hiking, golfing, shopping and more.

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, 177 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.

Top guest favourite
A charming exterior view showcases a white brick structure with a spacious porch, flanked by lush greenery and colorful flowerbeds. Two sets of large windows provide natural light to the inviting entryway, framed by decorative plants and wrought iron fencing.
Home in Anderson
4.99 out of 5 average rating, 143 reviews

Historic Eighth Guest house

You'll have a great time at this comfortable place to stay. The unit is set up similar to a duplex . Shared stairway to upper unit with lockbox entry to unit . 2 bedrooms , 1 bathroom, kitchen, sunroom, family room, dining room, laundry room. Adults only in this unit due to balconies . Owner also currently hosts Historic Eighth carriage house .

Popular amenities for Middletown holiday rentals

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