Vacation rentals in Pittsboro

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Top-rated vacation rentals in Pittsboro

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

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Guest favorite
Home in Brownsburg
4.96 out of 5 average rating, 96 reviews

Popular Suburb Getaway

Convenient PET FRIENDLY Suburb home (Brownsburg) offers this newly furnished OPEN LAYOUT 3 Bdrm 2 Ba RANCH w/attached garage, vaulted Great Room, Fully functional kitchen & laundry plus a fenced-in backyard & deck that overlooks a pond with fountain. This popular floorplan allows space and privacy. Located in the heart of Brownsburg & less than a mile walk to all kinds of different food & shopping. Conveniently located near I-74 with easy access to I-465, I-65, Downtown, Race tracks & Airport!

Top guest favorite
The entrance is accessed by a set of wooden stairs featuring a metal railing. A door with large windows is flanked by potted plants, providing a welcoming touch. Natural light filters through the greenery surrounding the entrance.
Guest suite in Indianapolis
4.99 out of 5 average rating, 104 reviews

A little secret hideaway

Keep it simple at this peaceful and centrally-located place. It’s close to everything, making it easy to plan your visit. It’s close to the airport, sporting events, and downtown. It’s up on the second level, but separate from the downstairs living. It has its own entrance and living space. 2.3 miles to Indianapolis airport 5.1 miles to Lucas Oil IRP 5.3 miles to Indianapolis Motor Speedway 8.3 miles to Lucas Oil Stadium 8.8 miles to Gainbridge Fieldhouse 8.8 miles to Indianapolis Downtown

Guest favorite
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, 127 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 favorite
Home in Brownsburg
4.86 out of 5 average rating, 22 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.

Top guest favorite
A charming exterior of the home is displayed, featuring a welcoming front porch with hanging planters. Lush green grass and colorful flower beds surround the property, while a paved path leads up to the entrance. A clear blue sky enhances the inviting appearance.
Home in Lizton
4.96 out of 5 average rating, 84 reviews

3 Bed + 2 Bath Family Home w/ Game Room

Welcome to our charming home in Lizton, IN! Just minutes from two stunning wedding venues and a short 30-minute drive to downtown Indianapolis, this recent remodel offers comfort and convenience. Enjoy a spacious, fully stocked kitchen with a coffee bar, a cozy living room with a fireplace and TV, a laundry room, and a lovely backyard seating area. With three bedrooms and two baths, our home comfortably accommodates eight guests. Perfect for wedding guests, families, or anyone visiting Indy!

Guest favorite
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, 206 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.

Superhost
The bungalow features a welcoming entrance with a wooden porch and railings. A light-colored exterior is complemented by several windows, allowing natural light. The surrounding grassy area adds to the home's pleasant curb appeal, while nearby structures can be partially seen in the background.
Home in Brownsburg
4.71 out of 5 average rating, 24 reviews

Cozy 2 BR Bungalow!

Congratulations! Your search stops here! Kick back & relax in this stylish 2 BR bungalow in Brownsburg, In. Located just 25 minutes from downtown Indy & 10 minutes from the world famous Indy 500. This handicap accessible home offers free wi-fi, Roku TV, private parking & more. The Primary Suite features a full bath w/double sinks & stand up shower. The Kitchen is beautiful & fully stocked. This home is clean & just minutes from restaurants, shopping & more. Truly, a great place to stay.

Top guest favorite
A charming front porch is showcased, featuring two red chairs flanking a small table. Colorful flowers are planted along the walkway and in garden beds, adding vibrancy. The light blue exterior of the bungalow is complemented by bright white trim, creating an inviting entrance.
Bungalow in Speedway
4.96 out of 5 average rating, 160 reviews

Vintage Racer @ Speedway

Indy's Longest-Running Airbnb Superhost This AUTHENTIC 1940, 1,740' bungalow was beautifully restored in 2016 The downstairs with kitchen and full bath was remodeled in 2019 3 blocks/10 minute walk to the main gate of the Indianapolis Motor Speedway 3 blocks to Main Street and all of the restaurants, coffee shops, pubs The driveway fits 4-5 cars Off-street parking for 3 more vehicles Mere steps to the walking trail 10 miles to the Indianapolis International Airport 6 miles to downtown Indy

Guest favorite
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 Indianapolis
4.94 out of 5 average rating, 132 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.

Guest favorite
Home in Brownsburg
4.88 out of 5 average rating, 17 reviews

Walkable Downtown Home | 3 King Beds + Cozy Charm

Your family will love this centrally located 1920s home with over 3,100 square feet of space to relax and enjoy! This charming 4-bedroom, 3-bathroom house blends classic character with modern comfort. Step outside and you’re just a short walk from all the new Brownsburg has to offer, including great restaurants, local bars, playgrounds, and walking trails. Whether you’re here to explore or simply kick back, this home has everything you need for a comfortable and memorable stay.

Guest favorite
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.
Camper/RV in Pittsboro
4.96 out of 5 average rating, 23 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 favorite
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, 612 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).

Popular amenities for Pittsboro vacation rentals

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