Holiday houses in Pittsboro

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Top-rated holiday rentals in Pittsboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
The front view of the house showcases a classic white exterior with a welcoming entrance. Lush green shrubs frame the entrance, and a driveway leads to a detached garage seen in the distance. A clear blue sky complements the home's inviting appearance.
Home in Brownsburg
4.84 out of 5 average rating, 124 reviews

Cozy and Comfortable, great Fall destination!

This house is an old model, but it is a cozy comfortable house and will everything you need for your stay. In Brownsburg it's only minutes from the Indianapolis Raceway Park and the Lucas Oil Raceway. There is plenty of entertainment and food options within driving distance and a couple you can walk to. I have wifi and streaming with a Fire Stick available on the TV. I do not have cable. I have Netflix, Disney, HBO. Feel free to bring your own Streaming Devices to access your own shows.

Guest favourite
The living room contains a gray sofa and two striped chairs, creating comfortable seating. Natural light enters through large windows adorned with white blinds. A round area rug is positioned on the floor, while a decorative piece hangs on the wall, contributing to the room's aesthetic.
Home in Lizton
4.91 out of 5 average rating, 22 reviews

Cozy Home w/ Bar Room + Huge Yard + Coffee Station

Welcome to your home away from home in Lizton, Indiana! This charming 2-bedroom, 1-bath house comfortably sleeps 6 guests, making it perfect for families or friends. Relax in the cozy bar room or enjoy the spacious backyard, complete with a fire pit—ideal for roasting marshmallows and making s'mores. Located just 30 minutes from Indianapolis and near two beautiful wedding venues, this retreat offers the perfect blend of comfort and convenience. Experience a memorable stay in a peaceful setting!

Top Guest favourite
A cozy living area is presented, featuring a comfortable gray sofa and an armchair with a patterned fabric. A wooden coffee table stands at center, while a light fixture and an artwork are included on the walls. Natural light filters through the white blinds of the window.
Cottage in Indianapolis
4.96 out of 5 average rating, 419 reviews

Hidden Orchard Guest Cottage

Enjoy your stay at our comfortable cottage, tucked away in a quiet neighborhood off the White River (10 min. from downtown & Broadripple; less than 5 min. drive from Newfields, 100 Acre Woods, and Butler University; AND walking distance to the Fitness Farm). Feel at home in this fully furnished cottage, with its up-to-date kitchen, cozy bedroom and tech-friendly living room, equipped with hi-speed Wi-Fi, Netflix and YouTube TV. There’s also a private patio with a fire pit for you to enjoy!

Guest favourite
Home in Brownsburg
4.93 out of 5 average rating, 15 reviews

Mid-Century Magic

Step into timeless style & comfort at this beautiful mid-century modern house. This single-level gem blends iconic 1950s design w/ contemporary touches to create the perfect getaway for couples, families, or remote workers seeking a peaceful escape. * 3 Bedrooms 2 Bathrooms Sleeps 6 * Cozy fireplace * Fully stocked modern kitchen * Large backyard & deck * WiFi smart TV Whether you're here to relax, attend a sporting event, or just soak in the vibes, this home offers a stay you won’t forget.

Guest favourite
A charming cottage exterior is framed by a blossoming tree in the foreground. The wooden deck features a railing and is accessible through a glass-paneled door. Nearby, lush green grass extends toward an open field in the background, suggesting a serene rural setting.
Farm stay in Thorntown
4.97 out of 5 average rating, 202 reviews

Heavenly Acres Farm and Learning Center

Experience a relaxing stay, spending time watching chickens happily foraging or barn animals as they graze in the pasture. Take a walk by the creek, taking in the country sunset.Enhance your experience by interacting with the animals during a farm tour or helping with daily chores. We also offer a variety of learning opportunities as we share how we process fiber, health care for animals or maybe a simple hay ride. Here at Heavenly Acres we want to provide you with a unique farm experience.

Guest favourite
Cabin in Greenbriar
4.94 out of 5 average rating, 127 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 welcoming living area features a light wood ceiling and modern furnishings. A comfortable sofa faces a round coffee table, surrounded by two leather armchairs. Natural light enters through the windows, while the adjacent kitchen area displays modern appliances and cabinetry.
Home in Speedway
4.96 out of 5 average rating, 288 reviews

Perfect 500 Location!

he perfect place to stay for all Indy events ! The whole group will enjoy easy access to everything from this centrally located place. WALK to the track! Two KING size beds! Off Street parking! Bicycles available for use for the weekends! (please request) Open layout for enjoying your travel partners. Wonderful opportunity at a great price. Close to Convention Center and all things downtown Indy too! Airport is 12 minutes away. Please, NO Cats or other type pets, beside dogs.

Guest favourite
The interior of the travel trailer features a compact kitchen with a sink, stove, microwave, and an ample countertop. A dinette area is visible, accompanied by wood grain flooring. A door leads to the outside, and a map of the United States is mounted on the wall.
Campervan/RV in Pittsboro
4.95 out of 5 average rating, 19 reviews

Relax & refresh in this 1+bd, 1 ba travel trailer

Like new 25' travel trailer at the back of a private, parklike 1 acre property. Everything you need to have a great experience outside of the hustle and bustle, especially for sporting events and other activities. Close to everything in and around the Indianapolis area, yet in a serene setting allowing for a relaxing time away from home. Fully stocked kitchen, outdoor table & chairs, camp chairs, with access to the parklike backyard with large fire pit, hammocks, & outdoor games.

Top Guest favourite
The exterior of a two-story guest house is surrounded by autumn foliage, showcasing wooden decking with a railing. The entrance features large windows, allowing natural light to brighten the space. A pathway leads from the front, bordered by seasonal plants.
Guesthouse in Brownsburg
4.86 out of 5 average rating, 605 reviews

Cozy Guest House in the Big Woods

Guest house located in the rear grounds of main home. Sidewalk access. 20 minute drive to downtown Indy.Full kitchen & 3/4 bath. This means toilet, sink & 42" shower (no tub).Entire house can sleep 1-3. Price is for 2 guests. Add’l fees for add’l guests & pets (no pit bulls) The upstairs has a king bed & down stairs a twin futon. This area is heavily wooded so the occasional critter can be seen & there will be spiders from time to time (part of wooded living).

Top 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, 198 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 spacious living area features a comfortable sectional sofa, light-colored walls, and a ceiling fan. A wooden coffee table sits on a patterned rug, complemented by a side lamp. An office chair is visible near a small table, providing a functional workspace.
Home in Brownsburg
4.92 out of 5 average rating, 134 reviews

Brownsburg House

1950's brick ranch w/ 3BR 1BA in the heart of Brownsburg furnished with furniture and supplies. Recently updated Kitchen and Bathroom. Easy drive to Downtown Indianapolis, Speedway (Home of the Greatest Spectacle in Racing) and Clermont (Lucas Oil Raceway). Located on a large lot with mature trees. Oversized Living Room and covered back porch make a great place to relax and enjoy your stay!

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
4.9 out of 5 average rating, 153 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.

Popular amenities for Pittsboro holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Hendricks County
  5. Pittsboro