Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Guest favourite
A spacious guest suite is illuminated by natural light from large windows. A cozy seating area is visible beside a desk and a wall-mounted television. Attractive bedding with striped patterns adorns a sizable bed, complemented by a plush carpet and tasteful decor.
Guest suite in Greenfield
4.91 out of 5 average rating, 105 reviews

Peaceful & Luxurious Suite

Our guest suite is close to Indpls--approx. 20 min from downtown. You’ll love our place because of the quiet & serene environment that's just outside of the city. We sit on an acreage close to the I70/Mt Comfort Road Exit making for quick access to and from the interstate. Our suite is in the front corner of our home. It has a private entrance with porch. It looks out into a garden that has a pond with fountain along with seating under a pergola. It has high ceilings and is very spacious.

Top guest favourite
The exterior of a historic brick building is displayed, featuring a prominent awning and colorful artwork in the windows. Decorative plants are arranged beneath the windows, adding a touch of charm. The building is set along a sidewalk, with neighboring structures visible.
Flat in Fairmount
4.96 out of 5 average rating, 222 reviews

Enjoy Nostalgia In James Dean's Hometown

The Rebel Lodge is a fully restored historic brick building located in the heart of James Dean's hometown. lt is right across the street from the James Dean Museum, just around the corner from Main street, and only blocks from The James Dean Gallery. The building will sleep 4-5 with a comfy double bed, a pull out sofa and an additional sofa. It is decorated with fun mid century furniture and decor. Everything is freshly up to date with new furnace, & air conditioning. Please enjoy your stay!

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, 247 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
A cozy sleeping area features a wooden bedframe adorned with a patchwork quilt. A bedside table holds a lamp and decorative items. Natural light from the window showcases the room's warm wooden walls and rustic charm, complemented by green accents and flowing curtains.
Guest house in Muncie
4.93 out of 5 average rating, 135 reviews

Quaint carriage house.

You’ll think you are in the country when you arrive at our peaceful 10 acre property right in Muncie. Located near our historic home, built in 1848, you’ll find a carriage house with an upstairs apartment with everything you need for a relaxing and comfortable stay. This is a quaint, rustic cabin like space with private outdoor area. You are only five to 10 minutes from BSU and IU Ball Hospital, downtown, Elm Street Brewing, the Children’s Museum, walking trails and most restaurants.

Superhost
A spacious bed is adorned with a white quilt and decorative pillows, including one with a design featuring a chocolate factory. Two bedside lamps provide soft lighting. A tray with a beverage and snack rests on the bed, complemented by a textured throw blanket at the foot.
Home in Anderson
4.84 out of 5 average rating, 204 reviews

Anderson Farm house all to yourself near AU

We are in the center of Anderson, a few blocks walking distance to Anderson University and a mile away from downtown. The house has been fully remodeled for our bnb guests. You will have the entire house just for yourself with private drive way and yard. The master bedroom is located on the main floor with a comfy king size bed. Second bedroom is upstairs with a twin size bed or can be expended to a king. We live 5 minutes away so we can always be there to help if you needed anything.

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, 121 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.

Top guest favourite
A spacious bedroom is featured with a plush area rug and sloped ceilings. A large bed, adorned with a textured blanket, is accompanied by a comfortable armchair and a side table. Natural light filters in through a window, illuminating the room.
Guest suite in Greenfield
4.96 out of 5 average rating, 217 reviews

Greenfield CountryCottage-minutes to downtown Indy

Beautiful, relaxing country cottage room is a perfect place to stay for your business trip or vacation. We provide clean and comfortable furnishings, along with a kitchenette and coffee bar. You will have total privacy, including a private driveway and entrance. Relax on the balcony with your morning coffee or after a busy day. Our room is located on a 2nd story with a private stairway to the entrance. Special discount on stays 3 days or more!

Top guest favourite
A modern kitchen is presented, featuring dark cabinetry and professional-grade stainless steel appliances. Open shelves display glassware and decorative items. A patterned rug contrasts with the light hardwood floor. A view into the adjoining living area can be seen, with natural light filtering through a window.
Home in Glendale
4.99 out of 5 average rating, 103 reviews

Designer 2 bedroom, 1 acre retreat in the city.

Welcome to the Honeysuckle Homestead. This is a completely updated 2 bedroom, 1.5 bathroom cottage with designer updated decor, nestled on a 1 acre wooded lot. Enjoy a peaceful morning on the trails or cooking a meal in a fully stocked kitchen. Adventure minutes away to Broadripple Avenue, Keystone Fashion Mall, Butler University, or a 15 minute drive to downtown Indianapolis. Quiet, safe neighborhood with ample parking and local ownership.

Guest favourite
A two-story house with a stone chimney is surrounded by trees and a spacious lawn. A wooden deck extends from the upper floor, offering outdoor seating. The gravel driveway leads to the entry, providing access below to garage spaces. The clear blue sky complements the serene atmosphere.
Home in Indianapolis
4.92 out of 5 average rating, 134 reviews

White River Retreat

Escape to a private retreat on the White River in Indianapolis! This custom-built home offers a peaceful, open-concept space with a stone fireplace, pool table, and jetted tub. Enjoy 12 acres of shared grounds with river access, kayaks, and fire pits. Perfect for a unique getaway, feeling worlds away yet close to everything. Ideal for couples or small groups seeking tranquility and adventure.

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, 332 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.

Popular amenities for Middletown holiday rentals

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