Holiday rentals 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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Guest favourite
Farm stay in Avon
5 out of 5 average rating, 7 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.

Guest favourite
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, 121 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
4.86 out of 5 average rating, 50 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
4.89 out of 5 average rating, 18 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!

Guest favourite
Guest suite in Mooresville
4.91 out of 5 average rating, 326 reviews

A room with view - great location

This room is a good value. It is close enough to Indianapolis yet peaceful, clean, quiet, and private. We are: 7.1 miles (10 minutes) from Indianapolis international airport. 18 miles (26 minutes) from downtown Indianapolis, 17miles (20 min drive) from Indianapolis convention center and Lucas stadium. 35 miles (52 minutes) from Indiana University in Bloomington. ~3 miles from I-70. If interested in booking please answer our pre booking questions found at the beginning of the house rules.

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, 106 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 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, 283 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.
Flat in Whitestown
4.95 out of 5 average rating, 61 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
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
4.95 out of 5 average rating, 257 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.

Top guest favourite
Flat in Indianapolis
4.98 out of 5 average rating, 417 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 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.
Guest house in Brownsburg
4.86 out of 5 average rating, 581 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).

Guest favourite
A modern living area features a stylish gray sofa adorned with decorative pillows. A circular glass coffee table sits on a soft area rug, with a floor lamp nearby. Large sliding glass doors lead to a balcony, framing a view of the outdoor space.
Flat in Perry Township
4.91 out of 5 average rating, 58 reviews

Refined Comforts: Luxe Stay in Whitestown Indiana

Indulge in luxury at our newly built 2023 apartment – a unique, tranquil 1-bedroom haven offering generous space for your comfort, accommodating up to 3 guests. Immerse yourself in the serenity of this quiet oasis, surrounded by a wealth of amenities. Conveniently located just 20 minutes away from downtown and 26 minutes from Indianapolis International Airport, modern design meets unparalleled relaxation in your ideal getaway!

Popular amenities for Pittsboro holiday rentals

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  4. Hendricks County
  5. Pittsboro