Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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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, 250 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
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, 94 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 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, 387 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
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, 140 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.

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, 202 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
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
4.91 out of 5 average rating, 105 reviews

White River Retreat

Welcome to paradise on the White River in Indianapolis! I personally designed, built, and lived in this house for six years - one of the best periods of my life. You will find a sense of peace and feel like you are in another world, all while being right in the middle of Indianapolis! Explore the river on the kayaks, bask in the sun, take in the wildlife. This river getaway is unbelievably unique. Your body and mind will thank you for staying here! Within two miles of anything you may need.

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
4.91 out of 5 average rating, 312 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
The living area features exposed wooden beams and a large stone fireplace as the focal point. A leather sofa is positioned across from a wooden coffee table. A patterned rug adds color to the rustic space, complemented by a decorative armchair and soft lighting from nearby lamps.
Cabin in Greenbriar
4.97 out of 5 average rating, 101 reviews

Kit’s Cabin - Log Cabin Retreat in Indianapolis

Welcome to our 150-year-old log cabin, nestled in the heart of Indianapolis! This cozy retreat offers a tranquil getaway while being just minutes away from all modern conveniences and only 20 minutes from downtown. Step inside and be greeted by the rich history of exposed wooden beams and a large stone fireplace. Our authentic rustic decor and cozy cabin amenities will transport you to a simpler time. Come experience the magic of Kit’s Cabin, where historic charm meets modern comfort.

Top guest favourite
A comfortable living area is highlighted by a caramel-colored sofa and two armchairs with decorative cushions. A wooden coffee table sits in the center, complemented by a woven basket and plants. Art prints hang on the wall, and a large TV is mounted nearby.
Home in New Castle
4.99 out of 5 average rating, 208 reviews

Entire Home with Modern Conveniences - New Castle

This home has been equipped with everything you need for a relaxing stay. Unwind in the evening while watching your 65” TV. The updated kitchen offers plenty of space for cooking dinner.The first bedroom features a King size bed and room darkening window treatments. The second bedroom offers a designated office space w/ high speed internet and a trundle bed. To start your day well, the bonus room offers a coffee bar with Nespresso and wellness area complete with treadmill and yoga space.

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, 133 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.

Top guest favourite
Flat in Indianapolis
4.98 out of 5 average rating, 413 reviews

Enjoy Comfort & History! - Suite w/ Private Entry

We look forward to welcoming you to a private suite that is the guest quarters in our home. You’ll have a private entrance & 3 rooms to yourself. There’s a living room with a table and chairs, a bedroom with a queen-size bed - nightstands, dresser and closet space with hangers for your use - and a newly remodeled full bathroom. There’s also a kitchenette in the hallway which is an antique Hoosier Cabinet equipped with a microwave, mini-fridge, coffee pot, and hot water pot.

Guest favourite
The exterior of the cozy casita is framed by lush greenery and features a welcoming entrance with a decorative sign. A wooden deck overlooks the tranquil river, complemented by outdoor seating. The pathway is lined with white gravel, enhancing the serene environment.
Cottage in Noblesville
4.97 out of 5 average rating, 201 reviews

Noblesville Riverfront house: Pet friendly, kayaks

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.

Popular amenities for Middletown holiday rentals

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