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
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, 125 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 charming entrance features a covered porch with two white rocking chairs. Colorful flowers surround the pathway, leading to a welcoming front door adorned with a decorative welcome sign. A light fixture is positioned above the door, enhancing the entrance's appeal.
Home in Noblesville
4.98 out of 5 average rating, 167 reviews

The Cozy Cottage

Enjoy a relaxing getaway in this cozy cottage. Historic Downtown Noblesville is just a short walk where you will find great restaurants, pubs, and boutique shops. The cottage consists of one bedroom, a fully equipped kitchen, and a full bathroom with walk-in shower. There’s also a fenced backyard with fire pit and furniture. The Cozy Cottage is centrally located near downtown Noblesville (2 min), Ruoff Music Center (15 min), Grand Park Sporting Complex (20 min), and over 100 miles of trails.

Guest favourite
Cabin in Indianapolis
4.95 out of 5 average rating, 129 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
A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.
Cabin in Bainbridge
4.94 out of 5 average rating, 108 reviews

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

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, 663 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.

Guest favourite
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 van/Motorhome in Pittsboro
4.95 out of 5 average rating, 20 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 favourite
A modern living area features a cozy sectional sofa, complemented by a sleek coffee table and decorative plants. A wall-mounted television is positioned above a linear fireplace. A green accent wall creates a vibrant backdrop, while framed artwork adds visual interest to the space.
Guest house in Fountain Square
4.97 out of 5 average rating, 183 reviews

The Fountain Square Flat - *No Cleaning Fee*

Step into your private guesthouse retreat in the heart of Fountain Square. This newly built, mid-century modern carriage house offers comfort, style, and total privacy. Enjoy fast Wi-Fi, self check-in, and free private parking— just over 1 mile from Lucas Oil Stadium and Gainbridge Fieldhouse and a short walk to restaurants, bars, and live music. Perfect for couples, solo travelers, or remote workers looking for a sleek, walkable stay in one of Indy’s most vibrant neighborhoods.

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, 609 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).

Top guest favourite
A modern three-story home features a striking façade with large windows framed by wooden accents. The structure's sleek design is complemented by a combination of dark siding and exposed concrete, set against a dynamic sky filled with clouds and warm hues of sunset.
Guest suite in Indianapolis
4.93 out of 5 average rating, 1,043 reviews

#IndyModPod Guest Suite Only! | No Cleaning Fees!

Hello, Fellow Traveler! Small, but mighty! This unique guest suite, located on the first floor of a modern three-story home, is perfect for short or extended stays. Enjoy all the essentials in a cozy space just steps away from some of Indy’s best neighborhood spots—restaurants, coffee shops, distilleries, and breweries! Plus, a quick stroll or bike ride down the iconic Monon Trail will take you to the vibrant Mass Ave dining and entertainment district!

Guest favourite
A small green house stands among trees, featuring a wooden deck at the entrance. Two white chairs are situated on the patio, and the structure has multiple windows that allow natural light to fill the interior.
Tiny home in Indianapolis
4.85 out of 5 average rating, 164 reviews

Cozy Tiny House Nestled in the Trees

Take it easy at this unique and tranquil getaway. In a charming tiny house surrounded by trees and birdsong, you can unplug and relax without going too far off the beaten path. Only a 15 minute drive from downtown, we’re conveniently located between Fountain Square, Irvington, Beech Grove, and Wanamaker. Curl up with a cup of tea and a good book, sit on the patio and watch for deer, or take a walk around our fledgling 9-acre permaculture farm.

Top guest favourite
A comfortable living space features a gray sectional sofa adorned with orange accent pillows. A round coffee table sits at the center, surrounded by a mix of seating options. Light enters through large windows, while a glimpse of the kitchen is visible in the background.
Loft in Mooresville
5 out of 5 average rating, 424 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!

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, 201 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.

Popular amenities for Pittsboro holiday rentals

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