Vacation rentals in Pittsboro

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pittsboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Carmel

4.9 out of 5 average rating, 355 reviews

Artist's Studio Retreat @ the Village of WestClay

Enjoy our genuine, one-of-a-kind experience. Nestled in the heart of architecturally inspired Village of WestClay, our artist studio has been converted into a Artist Retreat. Superhost since 2017 - regularly welcoming repeat guests. Ideal for business trips or extended escapes. Resort living - bar/restaurants and retail just steps away. Paths, trails, lakes, and 17 parks; just 15mins to Grand Park and 30 mins to downtown Indy. Suited for adult guests. Artist tools and art from travels abound.

Aug 5 – 12

G$22,509 GYD per night

Guest favorite

Home in Lebanon

4.97 out of 5 average rating, 128 reviews

House 3 mins off 65N/Dog Friendly/Fence! Very cln!

Very convenient location, a half mile from interstate 65. Walking distance to a great bakery; diner with outdoor (dog-friendly) seating; restaurants and a couple of bar and grills. This cute, 1 bdrm home has a carport & covered porch that works great as a doggie mudroom. Always professionally cleaned. There is a smart lock and security system, with cameras on the outside of house. This Airbnb was set up to help raise money eventually, for my new small animal rescue, chickennuggetandgang.com.

May 19 – 24

G$24,057 GYD per night

Guest favorite

Farm stay in Thorntown

4.97 out of 5 average rating, 136 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.

Jan 21 – 28

G$24,369 GYD per night

Guest favorite

Cabin in Martinsville

4.91 out of 5 average rating, 424 reviews

Grandpa's Cabin at Heidenreich Hollow

Grandpa’s Cabin at Heidenreich Hollow offers exclusive lodging for 6 on our hilly 5 acre wooded property. We offer a peaceful getaway from life while being right in the middle of both Indianapolis and Bloomington! Our quiet rustic cabin has a loft bedroom with stair access that includes a King size bed, 2 twin beds and an air mattress. We have a spacious bathroom and a fully equipped kitchen to help you feel at home. Search YouTube for Grandpas Cabin at Heidenreich Hollow for a video!

Apr 21 – 28

G$18,308 GYD per night

Guest favorite

Home in Brownsburg

4.94 out of 5 average rating, 161 reviews

Suburban Oasis

This home offers the best of both worlds - a 1960's mid century stone ranch with a completely remodeled contemporary interior. This bright, airy space offers plenty of room to relax on the couch in front of the TV, on the screened in patio, or in the backyard. With a full kitchen, laundry area, Wi-Fi, and spacious backyard - you'll miss none of the conveniences of home. Three bedrooms and 2 living rooms offer plenty of flexible sleeping arrangements for whomever you're traveling with.

Jun 14 – 21

G$51,487 GYD per night

Guest favorite

Home in Indianapolis

4.93 out of 5 average rating, 225 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.

Aug 15 – 22

G$22,166 GYD per night

Guest favorite

Guesthouse in Brownsburg

4.86 out of 5 average rating, 484 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 1-4. 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 queen size sofa bed & 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).

Sep 30 – Oct 7

G$24,577 GYD per night

Guest favorite

Home in Speedway

4.92 out of 5 average rating, 413 reviews

Adorable Bungalow 3 blocks from the 1st TURN

Cozy bungalow that lives bigger than it looks! Affordable luxury all at a terrific price! Fully private duplex has 2 stories and basement. We do allow dogs only, however I would like to know the breed & how many are staying. We do have some special "rules" for our furry friends! The neighborhood is walkable to restaurants, and very safe! Speedway boasts a low crime rate and wonderful neighbors! The airport is close & downtown is closer! 465 is just 1.5 miles to access 465

Nov 19 – 26

G$19,434 GYD per night

Guest favorite

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 499 reviews

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Close to Shades and Turkey Run State Parks. A great place to stay for the Covered Bridge Festival. 15 minutes to Wabash College and 25 minutes to DePauw University. We live on site. We clean the cottage in accordance with the CDC guidelines to ensure your stay is safe. Pets are allowed on a case by case basis. Please contact us to work out any details.

Sep 23 – 30

G$22,008 GYD per night

Guest favorite

Cabin in Carbon

4.97 out of 5 average rating, 108 reviews

Parke County Dream Cabin

Come experience the serenity of country living and get away from the daily grind of everyday life. Come fish in our five-acre lake (catch & release only), paddle-boat, kayak, or stroll through the woods. A covered porch and seating lakeside for relaxing. Located close to Mansfield and Bridgeton, 30 minutes from Turkey Run State Park, and only 30 minutes toTerre Haute or Greencastle. Come explore everything Parke County has to offer! KIDS WELCOME!

Oct 20 – 27

G$26,715 GYD per night

Guest favorite

Loft in Mooresville

5.0 out of 5 average rating, 276 reviews

Entire 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!

Aug 23 – 30

G$21,963 GYD per night

Guest favorite

Home in Indianapolis

4.92 out of 5 average rating, 919 reviews

Great Apt close to highway! N INDY *****

We are located in Castleton (Far North Indy) very close to restaurants, family-friendly activities, nightlife, & all the highways in Indy. Ruoff Music Center-12 min, downtown-20 min, Convention center-25 min, Grand Park-20 min, Airport-35 min. Apt has its own separate entrance w/keyless lock. Our place is good for couples/solo/business travelers/families w/small kids.

Feb 18 – 25

G$15,660 GYD per night