Pittsboro Holiday Rentals

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Our top choices for Pittsboro holiday rentals

Holiday Home in Indianapolis

Charming 2 Bedroom with in Home Gym
3.0 star property
9.4 out of 10, Exceptional, (3)
"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 NZ$541
includes taxes & fees
3 Jan - 4 Jan 2026
Charming 2 Bedroom with in Home Gym

Aparthotel in Downtown Indianapolis

CozySuites The Block Skybridge Access
4.0 star property
8.0 out of 10, Very good, (23)
"Came to town for the NCAA's and had a blast."
United States
Chris
The price is NZ$359
includes taxes & fees
28 Jan - 29 Jan 2026
CozySuites The Block Skybridge Access

Holiday Home in Near Northside

Carriage Home w/ early check in
9.2 out of 10, Wonderful, (14)
"Exactly as described, easy to check in Loved the early check-in "
United States
Kimberly S.
The price is NZ$212
includes taxes & fees
5 Jan - 6 Jan 2026
Carriage Home w/ early check in

Apartment in Downtown Indianapolis

The Residences at CityWay
4.0 star property
8.8 out of 10, Excellent, (137)
"Great place to stay, super location and walking distance to convention centre and shops"
Australia
Kenneth
The Residences at CityWay

Aparthotel in Downtown Indianapolis

CozySuites - Penrose
3.5 star property
8.4 out of 10, Very good, (8)
"Loved the pool area. Everyone we passed was so friendly. Apt had everything I needed to cook and even provided coffee so I didn’t have to go out to get any. Def will be back."
United States
Jessica
The price is NZ$361
includes taxes & fees
28 Jan - 29 Jan 2026
CozySuites - Penrose
2.0 star property
10.0 out of 10, Exceptional, (3)
"Very clean and reasonably priced for what you get!"
United States
Joseph
The price is NZ$423
includes taxes & fees
4 Jan - 5 Jan 2026
CozySuites Mass with parking, lounge and roof deck 10
9.0 out of 10, Wonderful, (23)
"Nice little spot to stay, if you are going to be out and about. "
United States
Payton G.
The price is NZ$498
includes taxes & fees
4 Jan - 5 Jan 2026
Red Door Cottage of Broad Ripple: Great Location!
10.0 out of 10, Exceptional, (27)
"Nice location clean and friendly host great for solo travel or with a significant other kitchen amenities were great perfect for quick meals with the stove top and the washer and dryer was a great add on bath room equipped with shampoo body wash and conditioner i loved it"
United States
Shonny K.
The price is NZ$279
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Affordable, Luxurious | Central Location
2.0 star property
9.8 out of 10, Exceptional, (15)
"The house was very comfortable and location was perfect for our needs. The owners were very quick to respond to our messages. Would stay again "
United States
Stephanie E.
The price is NZ$470
includes taxes & fees
7 Jan - 8 Jan 2026
Hot Tub in Indy! Downtown & Broad Ripple Nearby+EV

Apartment in Meridian-Kessler

Adorable Broad Ripple Duplex
3.5 star property
The price is NZ$547
includes taxes & fees
12 Jan - 13 Jan 2026
Adorable Broad Ripple Duplex

Apartment in Downtown Indianapolis

Stay Downtown Indy—Modern Comfort + Free Parking!
9.2 out of 10, Wonderful, (22)
"Need a two bedroom place to crash for a night. Amazing location and the accommodations were great. Would stay again if visiting Indy. "
United States
Slobodan S.
The price is NZ$507
includes taxes & fees
3 Jan - 4 Jan 2026
Stay Downtown Indy—Modern Comfort + Free Parking!

Apartment in Downtown Indianapolis

CozySuites Studio Apartment in Urban Indy
8.0 out of 10, Very good, (1)
"The unit is fine. Centrally located. Street parking costs extra, but isn't charged from 11p-7a, so if you pay for parking after 11p via the app, the paid parking time doesn't start until 7am. That was a bonus. They say they are pet-friendly, but be aware that there may be extra fees charged by the property after you book and pay, separate from VRBO."
United States
Jason C.
The price is NZ$337
includes taxes & fees
25 Jan - 26 Jan 2026
CozySuites Studio Apartment in Urban Indy

Apartment in Downtown Indianapolis

CozySuites at East Washington
3.0 star property
8.0 out of 10, Very good, (35)
"Great location walkable to a lot of places"
United States
Zach
The price is NZ$347
includes taxes & fees
28 Jan - 29 Jan 2026
CozySuites at East Washington
9.8 out of 10, Exceptional, (24)
"It was so nice to stay somewhere that was so centrally located to all the events we attended while we were In Indianapolis. "
United States
Anmarie K.
The price is NZ$556
includes taxes & fees
7 Jan - 8 Jan 2026
Modern Cottage | Near State Fairgrounds | Backyard

Apartment in Downtown Indianapolis

Experience Indy in Style Free Parking, DT Views
9.2 out of 10, Wonderful, (15)
"In town for a fever game, place worked out great for getting into town and going to the game. Will definitely stay again."
United States
Zacariah C.
The price is NZ$501
includes taxes & fees
3 Jan - 4 Jan 2026
Experience Indy in Style Free Parking, DT Views
9.4 out of 10, Exceptional, (59)
"The property is beautifully restored and in an interesting setting, nestled off of busy streets. It's close to the White River and has easy access to the Monon Trail."
United States
Constance W.
The price is NZ$526
includes taxes & fees
31 Dec - 1 Jan 2026
Remodeled Broad Ripple Bungalow Near Monon Trail

Holiday Home in Mapleton/Fall Creek

Midtown Modern Carriage Home |Near Top Attractions
9.6 out of 10, Exceptional, (25)
"Such a cute little place! We loved the stay! The owner was extremely responsive, the location was perfect and the bed was very comfortable!"
United States
Jamie H.
The price is NZ$399
includes taxes & fees
8 Jan - 9 Jan 2026
Midtown Modern Carriage Home |Near Top Attractions

Apartment in Downtown Indianapolis

BOLD 2BR/2BA In The Block Apartment by CozySuites
3.5 star property
10.0 out of 10, Exceptional, (3)
"Started a little rough with check in, but John handled quickly and professionally!! Stay was great!!! Quiet inside, but a little noisy outside due to downtown night life!!!! Overall, will definitely stay again if in the downtown Indy area!!!!"
United States
Erika
The price is NZ$583
includes taxes & fees
2 Jan - 3 Jan 2026
BOLD 2BR/2BA In The Block Apartment by CozySuites

Apartment in Downtown Indianapolis

The Argyle on Mass Ave
4.0 star property
9.0 out of 10, Wonderful, (149)
"Great location! A little loud but to be expected since it’s in a great location that is walkable to nice restaurants! Would stay again!"
United States
Jennifer
The Argyle on Mass Ave

Apartment in Downtown Indianapolis

CozySuitesThe Block w Skybridge Access 2
4.0 star property
8.0 out of 10, Very good, (3)
"Location is fantastic. Condo was decent for the price. Be aware though that the described futon is not in fact a futon but rather a wide sofa that is rather short. My daughter that is 5'5" barely fit on it. So just know that going in. The parking situation leaves you walking a block or so to and from the condo for $32 a day. An added expense that you need to consider when pricing a condo in the area. Overall, was pretty happy with the unit, but may have considered other options had I known in...
United States
shawn
The price is NZ$369
includes taxes & fees
4 Jan - 5 Jan 2026
CozySuitesThe Block w Skybridge Access 2
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

Everything you need to know about Pittsboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsboro holiday rentals we have selected for you start as low as NZ$208 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsboro rentals

At Expedia, we put the best Pittsboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Pittsboro?

Yes, there are holiday rentals close to the most popular sights in Pittsboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pittsboro has to offer?

Modern Carriage House Escape Rest Work Explore: This holiday home rental outside Pittsboro comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in Pittsboro?

While exploring the area, visit family-friendly sights like Dallara IndyCar Factory, or get outside and enjoy nature at Eagle Creek Park. In the wider area, you’ll find Lucas Oil Indianapolis Raceway Park and The Shops at Perry Crossing.

What are holiday rentals like in Pittsboro?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsboro. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for small groups.