Guesthouse holiday rentals in Indianapolis

Dreamy Carriage House in Historic Herron Morton

Cozy and colorful carriage house in Historic Herron Morton. Walking distance to restaurants, breakfast joints, coffee shops, downtown. Sip your coffee at the Juliette balcony, and take in the city views. Play cards till the wee hours, take an evening stroll through the neighborhood. Located on a peaceful side street in a historic Victorian neighborhood. Just north of Mass Ave and downtown. Close to I65/70, Lucas Oil Stadium, and Broadripple. Free street parking and well lit alley entrance.

Location · Value · Cleanliness

Eco-Friendly Downtown Indy Carriage House

Our carriage house (built 2019) sits behind our historic home on the near eastside of Indianapolis. We curated the space with the modern traveler in mind- from the design to the local coffee and art. We want your stay to give you the comforts of home while inspiring you by the city we love! A bright and modern space in a downtown neighborhood close to everything Indy has to offer! Close to Bottleworks, Mass Ave, and most downtown locations. Non-toxic supplies cleaning methods. Kids welcome!

Value · Family · Comfort

Private Carriage House in Historic Downtown

We have used Air BnB around the world and built this private carriage house with Air BnB guests in mind. Minimalist space is perfect for business travelers and those looking for a quick getaway. A quiet block and great downtown location within walking distance of the Mass Ave Cultural District, four micro breweries and on a bike lane for those who would like to travel further without a car. Sleeps 5 comfortably: 1 full sized bed, 1 full sized futon bed, 1 twin air mattress in a sleeping nook.

Location · Family · Nearby

The Fountain Square Flat - *No Cleaning Fee*

Step into your private guesthouse retreat in the heart of Fountain Square. This newly built, mid-century modern carriage house offers comfort, style, and total privacy. Enjoy fast Wi-Fi, self check-in, and free private parking— just over 1 mile from Lucas Oil Stadium and Gainbridge Fieldhouse and a short walk to restaurants, bars, and live music. Perfect for couples, solo travelers, or remote workers looking for a sleek, walkable stay in one of Indy’s most vibrant neighborhoods.

Location · Family · Comfort

Carriage house Ft. Square/close to downtown

Enjoy a private studio that is located in the Historic Fountain Square neighborhood. It is close to a variety of great restaurants and dining, art and culture, the city center. Within a 15 minute walk, you can be at the heart of all of the action of the conventions and activities that Indianapolis has to offer to the metropolitan region. It is within walking distance to the Cultural Trail, which leads through downtown and allows for walks or bike rides along the canal.

Location · Family · Quiet

Charming Meridian Kessler Carriage House

Built over a century ago and lovingly updated, this second-floor retreat sits in the heart of Meridian Kessler — one of Indy's most beloved midtown neighborhoods, walkable and tree-lined. Thoughtful touches throughout: curated furnishings, fiber WiFi, and a coffee setup worthy of a slow morning. Just right for one or two. Close to great food. Feels like home. Falling for Meridian Kessler? We're happy to share our favorite spots — and we know great realtors too.

Family · Location · Access

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).

Family · Location · Checkout

Bright Downtown Indy Studio Near Mass Ave Walkable

1BR studio in Cottage Home neighborhood, just east of downtown Indianapolis. Perfect for work trips, or a quiet weekend getaway. Walk to Mass Ave, Bottleworks, the Factory Arts District, top restaurants, shops, breweries. Minutes from Gainbridge Fieldhouse, Lucas Oil Stadium, and Monument Circle. Ideal for concerts, sports, and downtown events. Fully furnished with full-sized appliances and fast Wi-Fi. Warm, cozy, winter retreat! Sleeps 3 in two beds.

Value · Family · Long stay

Comfy private studio in historic Meridian Kessler

Enjoy this cozy, quiet, ground level studio in historic Indianapolis neighborhood of Meridian Kessler. Walk to restaurants, coffee shops, grocery stores, and pharmacy; Broad Ripple village with galleries and many restaurants 5 minutes away, and only a 15 minute drive to downtown Indianapolis. Private, secluded studio is detached from the main house in front, and has a full bath & kitchenette.

Location · Family · Condition

Adorable 2BD/1BA Guesthouse of Historic Home

Escape to our peaceful 2-bedroom guesthouse in a quiet Indianapolis neighborhood. This 725 sq. ft. retreat blends historic charm with modern art, featuring a full kitchen and dedicated office. Perfect for up to 4 guests seeking a quiet, stylish space just 15 blocks from downtown. Enjoy contactless check-in and the convenience of city living with a private, intimate feel.

Value · Location · Backyard

Perfect Downtown Carriage House - Walkable!

New construction, surrounded by history, in the middle of it all. Steps from Mass Ave and Bottleworks, feel at home in the king-sized Sleep Number bed, luxurious shower, and full kitchen, brand new appliances, including laundry. YouTube TV, Netflix, Prime, Disney+, MLBTV, and more all available on the TV! Great for a weekend getaway, even better for an extended stay.

Value · Location · Sleep quality

Private and Charming Carriage House Downtown Indy

Fully modern and new private space in my charming carriage house. It has all the amenities you would need to enjoy and explore the beautiful city of Indianapolis. If you are here for work or pleasure, it is perfectly located and easy access to all Indy has to offer so come and explore Indianapolis and all it has to offer.

Value · Family · Decor