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
Farm stay in Avon
5 out of 5 average rating, 3 reviews

Avon Farmhouse-Sleeps 14 Game Room, Hot Tub, Pond!

Spacious Family Retreat with Pool, Hot Tub & Game Room – Sleeps 14 | Avon, IN Gather your favorite people and escape to this stunning countryside retreat in Avon, Indiana — where comfort, fun, and relaxation come together on 10 peaceful acres. Designed for families and large groups, this spacious home comfortably sleeps up to 14 guests and offers every amenity you need for a memorable stay — including a private pool, hot tub, game room, and a scenic pond perfect for fishing or quiet reflection.

Top Guest favourite
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
5 out of 5 average rating, 66 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

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, 116 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
A quaint tiny house is nestled among greenery, featuring a modern entrance with a black door. Colorful flowers, primarily orange and purple, bloom alongside a concrete path that leads to the entrance, set against a backdrop of expansive lawns and trees.
Home in Avon
4.85 out of 5 average rating, 47 reviews

Tiny House Retreat!

Keep it simple at this peaceful and centrally-located cozy spot. Recently remodeled, this space has a fresh interior with lots of comfort. Kitchenette, spacious shower, comfortable beds! Located 25 minutes from downtown Indianapolis, 8 miles from the airport, & minutes away from coffee shops, grocery stores, hospitals, shopping, parks, restaurants, and more. The tiny house sits behind a small business. There’s plenty of privacy. The back parking lot is shared with the business. Huge yard!

Superhost
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
4.88 out of 5 average rating, 16 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!

Superhost
A single-story house is shown with a light grey exterior. The garage door is white, and a flag is displayed near the entrance. A manicured lawn extends in the front, framed by trees and adjacent homes under a clear blue sky.
Home in Brownsburg
4.91 out of 5 average rating, 23 reviews

Brownsburg B&B - 3(King)Bed 2Full Bath Home!

The Brownsburg B&B is the perfect place to unwind and feel right at home! Each of the three bedrooms has a spacious king bed to optimize your comfort. The living room is equipped with a deep couch for the ultimate relaxation & a smart TV for your viewing pleasure. The kitchen is stocked with the necessary supplies to cook as you wish. The location is ideal; the house is tucked in a cozy neighborhood right off of Main Street. Walk to local restaurants or take a quick drive to downtown. Enjoy!

Top 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, 191 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
A bright living room features two navy blue sofas and a coffee table, set on a light-colored area rug. Soft lamp light creates a cozy ambiance, while a wall mirror reflects the space. Natural light enters through a nearby window, enhancing the inviting environment.
Home in Indianapolis
4.91 out of 5 average rating, 278 reviews

Indianapolis Home Away From Home!

Super-cute 1960's ranch is only 1/4 mile from Lucas Oil Raceway (Home of the US Nationals), and only 6 miles from the famed Indianapolis Motor Speedway! All new furnishings, beds, appliances, paint and carpet in 2017! The bedrooms all have private locks. There are TWO full-size futons in the family room! Fully stocked kitchen, large fenced backyard...perfect for the whole family!! When setting booking, please provide the names of all guests and what your planned use for the house is.

Guest favourite
A bright living room features a grey sofa adorned with decorative pillows, complemented by a round wooden coffee table. Floor-to-ceiling windows are dressed in light grey curtains, allowing natural light to illuminate the space. A balcony is visible beyond the glass doors, furnished with outdoor seating.
Apartment in Whitestown
4.96 out of 5 average rating, 56 reviews

Serene 1BR: Perfect Indy Stay

Welcome to your ideal retreat in Whitestown, Indiana! Our modern 1-BR apartment is perfect for short or extended stays. Enjoy a bright living area, fully-equipped kitchen, and cozy bedroom with a queen-sized bed. Amenities include high-speed Wi-Fi, an in-unit washer and dryer, central heating and AC, free parking, a fitness center, and a pool. Conveniently located near dining, shopping, and just 20 minutes from downtown Indianapolis. Book now for a comfortable and convenient stay!

Top Guest favourite
Apartment in Indianapolis
4.98 out of 5 average rating, 410 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.

Top Guest favourite
A bright living area is featured, showcasing a green sofa with a decorative pillow. A wooden coffee table is positioned on a dark, patterned rug. A staircase leads to another level, while a contemporary television stand is visible nearby. Modern lighting illuminates the space.
Townhouse in Speedway
4.88 out of 5 average rating, 434 reviews

Style and Comfort in this adorable bungalow!

Cozy & upscale bungalow located in the heart of Speedway, Indiana. Enjoy a small, but polished bungalow built in the 1930s. 2 bedroom, fully stocked kitchen, fenced private yard, and great location to all things racing and Indy! 5 Short miles to downtown & a 15 minute drive to the convention center. 1 dog is welcome! (More with written permission) Please share a bit of the nature of your trip, your hometown, & breed of your dog. No Cats or other type animals.

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, 572 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 holiday rentals

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