Holiday houses in Pittsboro

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Top-rated holiday rentals in Pittsboro

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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, 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.

Top Guest favourite
A tranquil fire pit area features six wooden chairs arranged in a circular layout around a stone fire ring. The setting is surrounded by lush greenery, with the soft glow of sunset visible in the background.
Home in Whitestown
4.94 out of 5 average rating, 129 reviews

Florence Cottage~Modern Country

Relax with the whole family at Florence Cottage. Brand new home- quaint, quiet, and a great mix of country charm with stylish design. The house offers 4 bedrooms, 2 full bathrooms. The master suite has its own spacious master bathroom. Bedroom 2 and 3 are furnished with queen beds. Bedroom 4 offers a bunk bed. The home sits on an acre with stately mature trees, a fabulous front porch to take in the sunrise & then a new deck overlooking the large back yard boasting amazing sunsets at night!

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
4.94 out of 5 average rating, 123 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
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, 597 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
Home in Indianapolis
4.94 out of 5 average rating, 254 reviews

Hot tub getaway |Quiet 2bdrm Home | N. Broadripple

Hot tub getaway in north Broad Ripple! Relax after a long day in a private hot tub jacuzzi. Get some good sleep in a quiet bedroom. 5 min drive to charming Broad Ripple Ave (bars/shops), Keystone Fashion mall, Ironworks (upscale restaurants), Monon trail (walking/biking/dog friendly) 15 min drive to Butler University/Carmel/Fishers 20 min drive to Lucas Oil stadium/Mass ave/Fountain Sq/IUPUI/Grand park 30 min drive to Indianapolis Airporticst

Top Guest favourite
Loft in Mooresville
5 out of 5 average rating, 413 reviews

Loft Apartment: Beautiful Farm and Country Views

This beautiful, over the garage private apartment is located in a wooded area across from our 94 acre farm. A very peaceful setting to wind down and enjoy the nature around you. Conveniently located 15 minutes from the airport and 30 minutes from downtown Indianapolis. A work space is also available that overlooks this beautiful farm!! Also perfect for couples or small families to enjoy some time in the country!

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
4.96 out of 5 average rating, 183 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, 131 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!

Superhost
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
4.89 out of 5 average rating, 141 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.

Guest favourite
A modern bathroom features a freestanding soaking tub beside a glass-enclosed shower. Neutral tiles cover the floor, complemented by a stone accent area. A vanity with a sink and a wall-mounted clock adds functionality, while natural light enters through a window with a view of greenery.
Home in Indianapolis
4.94 out of 5 average rating, 163 reviews

Cozy Modern 3BR 20 mins Downtown & Grand Park

Spacious home sleeps up to 8. The master suite features a king bed, twin trundle, air mattress, 55” TV with soundbar, updated shower, soaking tub, and walk-in closet. Two additional bedrooms offer queen beds. Enjoy central air/heat, washer/dryer, smart lock, smoke alarms, and fire extinguisher. The kitchen includes a Keurig coffee maker for your stay.

Top Guest favourite
Home in Irvington
4.99 out of 5 average rating, 101 reviews

The Prescott- Bold Luxury. Historic Glamour

Welcome to the Prescott. An exciting, bold & fierce luxury rental in the heart of beautiful historic downtown Irvington. Just 5 miles from downtown Indianapolis. Enjoy this historic home built in 1908; reimagined & curated in 2024. Experience an upscale stay with modern comfort & historic elements where BOLD is always at the forefront.

Top Guest favourite
An open living area showcases high cathedral ceilings and four skylights that enhance natural light. A gray sofa is complemented by vibrant green and yellow pillows. A decorative wooden wall features a logo, while colorful artwork and a chic yellow chair contribute to the welcoming ambiance.
Guesthouse in Cottage Home
4.99 out of 5 average rating, 1,044 reviews

Private and Charming Carriage House Downtown Indy

Fully modern and new private space in my charming carriage house. It has all the amenities you would need to enjoy and explore the beautiful city of Indianapolis. If you are here for work or pleasure, it is perfectly located and easy access to all Indy has to offer so come and explore Indianapolis and all it has to offer.

Popular amenities for Pittsboro holiday rentals

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