Holiday rentals in Pittsboro

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Top-rated holiday rentals in Pittsboro

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Top guest favourite
An aerial view showcases a sprawling estate set on over 13 acres, featuring a landscaped yard with manicured grass. A large pond is visible in the background, surrounded by trees and established gardens. The elegant architecture of the buildings complements the serene outdoor environment.
Guest house in Carmel-by-the-Sea
5 out of 5 average rating, 16 reviews

Gated estate home, 10 minutes to Christkindlmarkt!

A private country escape in the heart of the suburbs on a 13+ acre gated estate property with old world charm! Accommodations include a semi-attached carriage home w/dedicated garage parking, fully equipped kitchen, W/D, access to commercial style fitness center, indoor half bball court with pickleball & plenty of outdoor living and areas to explore. -15 min to Grand Park -30 min or less to Lucas Oil/Gainbridge/IND/Speedway -10 min to Carmel Arts & Design District -10 min to Zionsville Village

Guest favourite
A modern bathroom features a freestanding soaking tub beside a glass-enclosed shower. Neutral tiles cover the floor, complemented by a stone accent area. A vanity with a sink and a wall-mounted clock adds functionality, while natural light enters through a window with a view of greenery.
Home in Indianapolis
4.94 out of 5 average rating, 158 reviews

Modern 3 BR, 20 min downtown / 25 mins Grand Park

This home sleeps a group of 8. The master suite has a king bed, a twin size trundle (2 beds), an air mattress, 52” TV w/sound bar, updated shower, soaking tub, and a large walk-in closet. The 2 other bedrooms: queens Safety and comfort are important. Central air and heating are throughout this home. There is a washer and dryer and for guests’ safety, this home is equipped with a Smart Lock system, smoke alarms and a fire extinguisher. In the kitchen, we have a Keurig coffee maker for guests

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, 120 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.

Superhost
The living room contains a gray sofa and two striped chairs, creating comfortable seating. Natural light enters through large windows adorned with white blinds. A round area rug is positioned on the floor, while a decorative piece hangs on the wall, contributing to the room's aesthetic.
Home in Lizton
4.88 out of 5 average rating, 17 reviews

Cozy Home w/ Bar Room + Huge Yard + Coffee Station

Welcome to your home away from home in Lizton, Indiana! This charming 2-bedroom, 1-bath house comfortably sleeps 6 guests, making it perfect for families or friends. Relax in the cozy bar room or enjoy the spacious backyard, complete with a fire pit—ideal for roasting marshmallows and making s'mores. Located just 30 minutes from Indianapolis and near two beautiful wedding venues, this retreat offers the perfect blend of comfort and convenience. Experience a memorable stay in a peaceful setting!

Guest favourite
The backyard features a spacious lawn surrounded by trees and a wooden deck equipped with patio seating. The home’s screened porch is visible, providing a comfortable outdoor area. A fully fenced perimeter ensures privacy, making it suitable for children and pets.
Home in Indianapolis
4.87 out of 5 average rating, 172 reviews

Speedway! Downstairs BR+Dog friendly+Fenced Yard

Spacious 2,000 ft2 modern home equipped with smart home technology, located in a residential neighborhood. Our home was designed with family & group getaways in mind. You will enjoy the comfort of a large, updated home with space to spread out, a screened-in porch along with a fully fenced backyard which kids & dogs would love, and convenient parking! Great for work or play! IMS Speedway - 4 miles Downtown (Lucas Oil, Convention center, Victory Field) - 8.9 miles Children's Museum - 9.6 miles

Top guest favourite
A charming cottage exterior is framed by a blossoming tree in the foreground. The wooden deck features a railing and is accessible through a glass-paneled door. Nearby, lush green grass extends toward an open field in the background, suggesting a serene rural setting.
Farm stay in Thorntown
4.97 out of 5 average rating, 193 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.

Top guest favourite
The kitchen features dark wood cabinetry and stainless steel appliances, including a microwave and oven. A circular dining table with colorful dishware is visible. Light enters through the window, illuminating the hexagonal tile flooring, enhancing the functional layout.
Home in Speedway
4.92 out of 5 average rating, 530 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. The airport is close & downtown is closer! 465 is just 1.5 miles to access 465. Please no cats, or other type of pet.

Top guest favourite
The living area features exposed wooden beams and a large stone fireplace as the focal point. A leather sofa is positioned across from a wooden coffee table. A patterned rug adds color to the rustic space, complemented by a decorative armchair and soft lighting from nearby lamps.
Cabin in Greenbriar
4.97 out of 5 average rating, 103 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
The living area features a comfortable couch adorned with decorative pillows, complemented by two accent tables. Two lamps on either side provide soft lighting, while framed artwork and a window dressed in sheer curtains enhance the inviting atmosphere.
Home in Brownsburg
4.94 out of 5 average rating, 177 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.

Guest favourite
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, 283 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.

Guest favourite
A charming gray house features a welcoming porch supported by white columns. A small rocking chair and hanging plants enhance the outdoor space. Steps lead up to the entrance, framed by manicured bushes and decorative stones, with a flag displayed nearby.
Home in Irvington
4.88 out of 5 average rating, 598 reviews

Historic Charmer

My home is a very quaint, clean, and private space in a very walkable and welcoming community. Historic Irvington is full of several eateries, coffee shops and a brewery within steps. Just follow the Pensey Trail south a block to explore this exciting community. Or, take the trail for a light run or bike ride! Minutes from downtown my space is perfect for a weekend away, a cozy bed while out traveling, or an easy effortless way to travel for work or one of Indy’s many great conventions.

Guest favourite
A bright living room features a grey sofa adorned with decorative pillows, complemented by a round wooden coffee table. Floor-to-ceiling windows are dressed in light grey curtains, allowing natural light to illuminate the space. A balcony is visible beyond the glass doors, furnished with outdoor seating.
Flat in Whitestown
4.95 out of 5 average rating, 60 reviews

Serene 1BR: Perfect Indy Stay

Welcome to your ideal retreat in Whitestown, Indiana! Our modern 1-BR apartment is perfect for short or extended stays. Enjoy a bright living area, fully-equipped kitchen, and cozy bedroom with a queen-sized bed. Amenities include high-speed Wi-Fi, an in-unit washer and dryer, central heating and AC, free parking, a fitness center, and a pool. Conveniently located near dining, shopping, and just 20 minutes from downtown Indianapolis. Book now for a comfortable and convenient stay!

Popular amenities for Pittsboro holiday rentals

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