Vacation rentals in Pittsboro

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Top-rated vacation rentals in Pittsboro

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Top guest favorite
A cozy living area is highlighted by a three-bulb brass chandelier above a tan sofa, complemented by a wooden table. The wall features an arrangement of framed mirrors in gold and silver tones, while a doorway leads to other areas of the carriage house.
Guesthouse in Meridian Kessler
4.99 out of 5 average rating, 250 reviews

Charming Meridian Kessler Carriage House

Second floor carriage house in historic Indianapolis neighborhood. Renovated and with original architectural details like the hardwood floors. This cozy space is perfect for one or two people looking for a convenient midtown Indy location. Safe walkable neighborhood close to many restaurants. We've made the space a beautiful home away from home - lovely linens, fiber wifi and an excellent coffee machine. Like our space, but aren't coming to Indy? Message and we'll send you the shopping link.

Guest favorite
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, 121 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 favorite
A comfortable living area is depicted, featuring a light-colored sofa adorned with patterned cushions. A glass coffee table sits in front, with decorative items displayed. Soft lighting from two floor lamps and a nearby potted plant adds a touch of greenery to the space.
Cottage in Indianapolis
4.98 out of 5 average rating, 434 reviews

Luxe 1BR Cottage with Private Backyard

We’re offering great value to guests w/ a history of positive reviews only, if your accustomed to perfect neighborhoods, this may not be for you Urbn 900sf cottage in Indy's Eastside. A+ home in redeveloping area. Easy access to DT, I70 & I65, MassAv, FountainSq & Irvington.The home dates back to 1890's & has been completely renovated w/beautifully appointed interior. Kingbed, 2-smart TV's, custom kit & luxe bath w/heated flrs.If you can appreciate a "comeback" story, then this home is for you

Top guest favorite
A cozy living area is presented, featuring a comfortable gray sofa and an armchair with a patterned fabric. A wooden coffee table stands at center, while a light fixture and an artwork are included on the walls. Natural light filters through the white blinds of the window.
Guesthouse in Indianapolis
4.97 out of 5 average rating, 381 reviews

Hidden Orchard Guest Cottage

Enjoy your stay at our comfortable cottage, tucked away in a quiet neighborhood off the White River (10 min. from downtown & Broadripple; less than 5 min. drive from Newfields, 100 Acre Woods, and Butler University; AND walking distance to the Fitness Farm). Feel at home in this fully furnished cottage, with its up-to-date kitchen, cozy bedroom and tech-friendly living room, equipped with hi-speed Wi-Fi, Netflix and YouTube TV. There’s also a private patio with a fire pit for you to enjoy!

Guest favorite
Guest suite in Mooresville
4.91 out of 5 average rating, 328 reviews

A room with view - great location

This room is a good value. It is close enough to Indianapolis yet peaceful, clean, quiet, and private. We are: 7.1 miles (10 minutes) from Indianapolis international airport. 18 miles (26 minutes) from downtown Indianapolis, 17miles (20 min drive) from Indianapolis convention center and Lucas stadium. 35 miles (52 minutes) from Indiana University in Bloomington. ~3 miles from I-70. If interested in booking please answer our pre booking questions found at the beginning of the house rules.

Guest favorite
Home in Brownsburg
4.92 out of 5 average rating, 12 reviews

Mid-Century Magic

Step into timeless style & comfort at this beautiful mid-century modern house. This single-level gem blends iconic 1950s design w/ contemporary touches to create the perfect getaway for couples, families, or remote workers seeking a peaceful escape. * 3 Bedrooms 2 Bathrooms Sleeps 6 * Cozy fireplace * Fully stocked modern kitchen * Large backyard & deck * WiFi smart TV Whether you're here to relax, attend a sporting event, or just soak in the vibes, this home offers a stay you won’t forget.

Top guest favorite
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
4.93 out of 5 average rating, 534 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.

Superhost
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 favorite
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.
Apartment in Whitestown
4.95 out of 5 average rating, 62 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!

Top guest favorite
Apartment in Indianapolis
4.98 out of 5 average rating, 418 reviews

Enjoy Comfort & History! - Suite w/ Private Entry

We look forward to welcoming you to a private suite that is the guest quarters in our home. You’ll have a private entrance & 3 rooms to yourself. There’s a living room with a table and chairs, a bedroom with a queen-size bed - nightstands, dresser and closet space with hangers for your use - and a newly remodeled full bathroom. There’s also a kitchenette in the hallway which is an antique Hoosier Cabinet equipped with a microwave, mini-fridge, coffee pot, and hot water pot.

Top guest favorite
A modern kitchen is equipped with sleek white cabinetry and a stainless steel refrigerator. Counter space is available, alongside a stove and an oven. Open shelving displays glassware, with pots and utensils hanging for easy access. Natural light filters through a window, complementing the neutral tones.
Home in Indianapolis
4.93 out of 5 average rating, 162 reviews

My little Speedway house

Cozy and upscale bungalow located in the heart of Speedway, Indiana.. Enjoy a small, but polished bungalow built in the 1930s. 2 bedroom, fully stocked kitchen, fenced private yard, and great location to all things racing and Indy! 5 Short miles to downtown and a 15 minute drive to the convention center. 1 dog is welcome! (More with written permission) Please share a bit of the nature of your trip, your hometown, & breed of your dog. No cats or other type animals, please.

Guest favorite
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.
Guesthouse in Brownsburg
4.86 out of 5 average rating, 581 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).

Popular amenities for Pittsboro vacation rentals

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  4. Hendricks County
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