Pittsboro Vacation Rentals

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Our top choices for Pittsboro vacation rentals

Vue by Stylish Stays

Vue by Stylish Stays
4.0 star property
Downtown Indianapolis
The price is CA $114
CA $313 total
includes taxes & fees
Jun 8 - Jun 9
Vue by Stylish Stays

Adorable Broad Ripple Duplex

Adorable Broad Ripple Duplex
3.5 star property
Meridian-Kessler
10.0 out of 10, Exceptional, (3 reviews)
"The home was very comfortable and cozy. Great location walking distance from restaurants n shops. "
United States
Lenita
The price is CA $115
CA $465 total
includes taxes & fees
Jun 8 - Jun 9
Adorable Broad Ripple Duplex

Chic Boho Retreat Near Downtown

Chic Boho Retreat Near Downtown
3.0 star property
Indianapolis
The price is CA $271
CA $1,317 total
includes taxes & fees
Jun 8 - Jun 9
Chic Boho Retreat Near Downtown

Modern Carriage House Escape Rest Work Explore

Modern Carriage House Escape Rest Work Explore
2.0 star property
Indianapolis
10.0 out of 10, Exceptional, (1 review)
"Clean"
United States
Laura
The price is CA $177
CA $517 total
includes taxes & fees
Jul 5 - Jul 6
Modern Carriage House Escape Rest Work Explore

2 Bedroom with Finished Basement Duplex Close to Downtown Indianapolis

2 Bedroom with Finished Basement Duplex Close to Downtown Indianapolis
Near Eastside
9.0 out of 10, Wonderful, (44 reviews)
"Easy to find…clean and great communication with the owner. "
United States
Sarah
The price is CA $152
CA $343 total
includes taxes & fees
Jun 8 - Jun 9
2 Bedroom with Finished Basement Duplex Close to Downtown Indianapolis

Cozy, Affordable, Luxurious | Central Location

Cozy, Affordable, Luxurious | Central Location
Meridian-Kessler
10.0 out of 10, Exceptional, (33 reviews)
"The host was attentive and the room was clean and cozy! So many amenities too! "
United States
Trevor W.
The price is CA $97
CA $230 total
includes taxes & fees
Jun 7 - Jun 8
Cozy, Affordable, Luxurious | Central Location

Pet-friendly house 5 minutes from Lucas Oil/Gainbridge!

Pet-friendly house 5 minutes from Lucas Oil/Gainbridge!
Indianapolis
8.8 out of 10, Excellent, (22 reviews)
"Very nice house and close to downtown!"
United States
Kevin L.
The price is CA $125
CA $295 total
includes taxes & fees
Jun 18 - Jun 19
Pet-friendly house 5 minutes from Lucas Oil/Gainbridge!

1 Queen Bed | Mobil Access Tub Ste Smk Ktchn

1 Queen Bed | Mobil Access Tub Ste Smk Ktchn
Indianapolis IN
10.0 out of 10, Exceptional, (44 reviews)
"It was fine,"
United States
Anonymous traveller
The price is CA $113
CA $131 total
includes taxes & fees
Jul 1 - Jul 2
1 Queen Bed | Mobil Access Tub Ste Smk Ktchn

Kit’s Cabin - Log Cabin Retreat in Indianapolis

Kit’s Cabin - Log Cabin Retreat in Indianapolis
Indianapolis
10.0 out of 10, Exceptional, (40 reviews)
"Had a great stay. Cabin was cozy and clean. The host left great instructions for everything. "
United States
Brittany S.
The price is CA $166
CA $372 total
includes taxes & fees
Jun 11 - Jun 12
Kit’s Cabin - Log Cabin Retreat in Indianapolis

Walk Everywhere! Sleek Fountain Square Stay

Walk Everywhere! Sleek Fountain Square Stay
3.0 star property
Fountain Square
The price is CA $169
CA $336 total
includes taxes & fees
Jun 7 - Jun 8
Walk Everywhere! Sleek Fountain Square Stay

Family Getaway Queen Beds w/ Large Porch

Family Getaway Queen Beds w/ Large Porch
Fountain Square
9.6 out of 10, Exceptional, (109 reviews)
"Walking distance to fountain square. Had a great visit, we would come back again."
United States
Matthew K.
The price is CA $136
CA $424 total
includes taxes & fees
Jun 7 - Jun 8
Family Getaway Queen Beds w/ Large Porch

Charming 2 Bedroom with in Home Gym

Charming 2 Bedroom with in Home Gym
3.0 star property
Indianapolis
7.8 out of 10, Good, (7 reviews)
"Nice option vs. a hotel. Clean, nice garage parking space and overall vey quaint! I would stay here again if given the opportunity!"
United States
Kenneth
The price is CA $115
CA $465 total
includes taxes & fees
Jun 22 - Jun 23
Charming 2 Bedroom with in Home Gym

Hot Tub+Arcade / Fire Pit Retreat Near Monon Trail

Hot Tub+Arcade / Fire Pit Retreat Near Monon Trail
Indianapolis
10.0 out of 10, Exceptional, (21 reviews)
"House is very clean and host was communicative. Really enjoyed our stay. "
United States
Maggie D.
The price is CA $150
CA $405 total
includes taxes & fees
Jun 24 - Jun 25
Hot Tub+Arcade / Fire Pit Retreat Near Monon Trail

Historic Downtown Indy Neighborhood Calvary

Historic Downtown Indy Neighborhood Calvary
Fountain Square
9.8 out of 10, Exceptional, (16 reviews)
"The Vrbo was clean and the owner was professional and helpful. We had a wonderful stay."
United States
Tucker K.
The price is CA $181
CA $552 total
includes taxes & fees
Jun 7 - Jun 8
Historic Downtown Indy Neighborhood Calvary

Magnificent 2 Bedroom, Loft Close to Downtown Duplex

Magnificent 2 Bedroom, Loft Close to Downtown Duplex
Near Eastside
9.2 out of 10, Wonderful, (39 reviews)
"Exceptional stay! "
United States
Chrissy S.
The price is CA $198
CA $404 total
includes taxes & fees
Jun 10 - Jun 11
Magnificent 2 Bedroom, Loft Close to Downtown Duplex

Top Floor - Mass Ave in Heart of Indy with Balcony

Top Floor - Mass Ave in Heart of Indy with Balcony
Downtown Indianapolis
10.0 out of 10, Exceptional, (9 reviews)
"Photos exactly match listing, great stay, nice location, good communication."
United States
Stephen L.
The price is CA $127
CA $255 total
includes taxes & fees
Jun 10 - Jun 11
Top Floor - Mass Ave in Heart of Indy with Balcony

King Bed+Game Room+Parking+Broadripple+Restaurants

King Bed+Game Room+Parking+Broadripple+Restaurants
Warfleigh
9.4 out of 10, Exceptional, (109 reviews)
"Cozy and close to everything "
United States
Janel F.
The price is CA $136
CA $247 total
includes taxes & fees
Jun 21 - Jun 22
King Bed+Game Room+Parking+Broadripple+Restaurants

New Indy Game House- Theater + Arcade - Sleeps 12

New Indy Game House- Theater + Arcade - Sleeps 12
Indianapolis
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay! Close to downtown especially the Stadium! Exactly as described."
United States
Stacey N.
The price is CA $257
CA $568 total
includes taxes & fees
Jun 10 - Jun 11
New Indy Game House- Theater + Arcade - Sleeps 12

4 BRs+King Bed+Game Room+Broadripple+Bars+Spacious

4 BRs+King Bed+Game Room+Broadripple+Bars+Spacious
Meridian-Kessler
9.8 out of 10, Exceptional, (63 reviews)
"Older home with lots of charm"
United States
Courtney P.
The price is CA $136
CA $275 total
includes taxes & fees
Jun 15 - Jun 16
4 BRs+King Bed+Game Room+Broadripple+Bars+Spacious

Charming 1-bedroom carriage house apartment with private garage

Charming 1-bedroom carriage house apartment with private garage
Downtown Indianapolis
9.8 out of 10, Exceptional, (16 reviews)
"I enjoyed my stay. I would definitely recommend this place!"
United States
milayah H.
The price is CA $139
CA $297 total
includes taxes & fees
Jun 8 - Jun 9
Charming 1-bedroom carriage house apartment with private garage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsboro Hotel Reviews

Find out more about Pittsboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Pittsboro?

Yes, there are vacation rentals near well known sights in Pittsboro, or you can select a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Pittsboro?

Newly Rennovated Home next to Zoo and Downtown Stadiums: Visitors like this Pittsboro vacation home rental. It is located in the city center and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

What can I see and do in Pittsboro?

While exploring the area, visit family-friendly sights like Indianapolis Zoo, or get outside and enjoy nature at Eagle Creek Park. In the larger area, you’ll find Indianapolis Motor Speedway and Lucas Oil Indianapolis Raceway Park.

What are vacation rentals like in Pittsboro?

A vacation rental is a private property you can book for a few weeks or just a few days in Pittsboro. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.