Holiday houses in Pittsboro

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Top-rated holiday rentals in Pittsboro

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Top Guest favourite
A cozy living area is highlighted by a three-bulb brass chandelier above a tan sofa, complemented by a wooden table. The wall features an arrangement of framed mirrors in gold and silver tones, while a doorway leads to other areas of the carriage house.
Guesthouse in Meridian Kessler
4.99 out of 5 average rating, 251 reviews

Charming Meridian Kessler Carriage House

Second floor carriage house in historic Indianapolis neighborhood. Renovated and with original architectural details like the hardwood floors. This cozy space is perfect for one or two people looking for a convenient midtown Indy location. Safe walkable neighborhood close to many restaurants. We've made the space a beautiful home away from home - lovely linens, fiber wifi and an excellent coffee machine. Like our space, but aren't coming to Indy? Message and we'll send you the shopping link.

Top Guest favourite
A landscaped garden area features stepping stones leading toward a green pathway. Lush plants and small yellow ornaments are visible, framed by trees and greenery. A decorative figure is placed among the stones, providing an inviting touch to the natural setting.
Guest suite in Indianapolis
4.86 out of 5 average rating, 379 reviews

Garden Flat/Parking/WasherDryer/Close 2 All Things

Relax & unwind in our private Garden Retreat. Our MCM home was built in 1954 and is a gem hidden in the city. Modernized without comprise to the history. Acres & acres of trees and wildlife to enjoy. Minutes to Newfields Art Museum and Downtown Indianapolis. Minutes to the quaint area of Broadripple and many of the best locally own restaurants and pubs in the city. Close 2 Butler & Marion Universities & IUPUI Campus. And the beautiful & historic homes of Meridian Kessler are seconds away

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.

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.
Guesthouse in Indianapolis
4.97 out of 5 average rating, 387 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
Guest suite in Mooresville
4.91 out of 5 average rating, 329 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.

Superhost
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, 284 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.

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, 267 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 exterior of the apartment is shown, featuring a combination of stone and siding. A small staircase leads to the entrance, with a decorative white railing. Colorful flowers bloom in the garden, while trees provide a natural backdrop against a clear blue sky.
Guest suite in Indianapolis
4.96 out of 5 average rating, 649 reviews

Beautiful 9 acre urban farm on NW side of Indy!

Welcome to our 1 bedroom attached apartment, The Blue Heron. Tucked back off the road on 9 acres, your apartment will have its own private entrance and parking area. During your stay you can wander through the woods, relax on the porch with a view, spend time with our chickens or stay inside your cozy apartment. Just minutes away from downtown Indianapolis, the Speedway or beautiful Eagle Creek Park, you’ll have easy access to city life with the peace and serenity of the country.

Top Guest favourite
Apartment in Indianapolis
4.98 out of 5 average rating, 421 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.
Guesthouse in Brownsburg
4.86 out of 5 average rating, 585 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).

Superhost
An open-concept living space features a dining area with a wooden table surrounded by black chairs, seamlessly connected to a modern kitchen equipped with stainless steel appliances. Natural light pours in through a large window, highlighting the minimalist decor and inviting atmosphere.
Home in Indianapolis
4.84 out of 5 average rating, 129 reviews

Carriage Home w/ early check in

Discover the perfect blend of historical charm and modern convenience in our cozy home, located in the heart of Indianapolis' Old North Side. Offering early check-in, you can kick-start your exploration of the city without a moment's delay. Our prime location ensures you're just moments away from downtown's bustling scene, the Indiana Convention Center, Gainbridge Fieldhouse, and Lucas Oil Stadium. Free Parking Free Coffee

Top Guest favourite
The living area features a comfortable gray sofa and two armchairs, inviting relaxation. A round coffee table sits at the center, with a soft area rug underneath. The space is filled with natural light, complemented by warm lamps, while shelves in the background house decorative items.
Loft in Mooresville
5 out of 5 average rating, 402 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!

Popular amenities for Pittsboro holiday rentals

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