Holiday houses in Indianapolis

The Jewel Box—Historic Tiny Home—Walk Downtown

Experience the charm of The Jewel Box, a beautifully renovated 1924 tiny home in the historic Indianapolis neighborhood of Windsor Park. Just steps from the Monon Trail, lush 31-acre Spades Park, & minutes from the trendy and upscale hub of the city: Mass Ave & the Bottleworks area. Enjoy boutique shops, lively bars, entertainment, & fine dining all within walking distance. With rich jewel tones, layered textures, & colorful artwork, the space offers playful luxury in a cozy, artistic retreat.

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!

Skyline View Condo, Best downtown spot, Park FREE!

There’s no better place to explore downtown Indy than our stylish condo in the heart of it all. We have free parking on site, but you won’t need your car! Step outside the front door and make your way to the vibrant entertaining and dining options of Mass Ave and The Bottleworks District, or stroll the historic cobblestone streets of Lockerbie. Wineries, breweries, coffee shops, antique dealers and entertainment venues are all minutes away. At night, you’ll enjoy the sparkling skyline view.

McOuat Place 4A Downtown Suite

Experience the heart of downtown Indianapolis from our modern, spacious loft at McOuat Place. Perfectly designed for comfort and convenience, this apartment is your ideal base for business, leisure, or special events. You are situated in the vibrant heart of downtown Indy, with the city's best attractions, dining, and entertainment steps from your door. Immerse yourself in the energy of the city, knowing your comfortable loft is just a short walk away from everything you want to see and do.

Free Parking · Skywalk · Walkable Downtown 1BR

🏙️ The Loft Suite The ONLY downtown apartment building with Skywalk access — walk indoors to the Convention Center, Lucas Oil & restaurants without stepping outside. Save $44/day with FREE garage parking. ⭐ "Beautiful apartment — even more beautiful than the pictures! Perfect location for taking the Skywalk to the convention center or Lucas Oil!" —Brittany Modern 1BR with city views · queen + sofa bed (sleeps 4). Fully stocked, fast WiFi, in-unit laundry. Superhost · Guest Favorite.

Bates Hendricks Luxe with Roof Deck

I am so excited to share my beautiful house with you, located in the Bates Hendricks neighborhood of Indy. Close to Fountain Square, Lucas Oil Stadium, Gainbridge Fieldhouse and lots more fun. The house has 3 beautiful bedrooms, 2 ensuite. There is a lounge upstairs with a comfy leather futon for more sleeping room. Off that is a beautiful roof deck with gas BBQ, firepit and dining for 6+. Also located on the same street as the famous HGTV Good Bones girls shop. Come visit Indy!

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.

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.

#IndyModPod Guest Suite Only! | No Cleaning Fees!

Hello, Fellow Traveler! Small, but mighty! This unique guest suite, located on the first floor of a modern three-story home, is perfect for short or extended stays. Enjoy all the essentials in a cozy space just steps away from some of Indy’s best neighborhood spots—restaurants, coffee shops, distilleries, and breweries! Plus, a quick stroll or bike ride down the iconic Monon Trail will take you to the vibrant Mass Ave dining and entertainment district!

Downtown Private Suite Convention Center Access

The Gallery is a 2 bedroom 1.5 bathroom suite with amazing city views. Located on Illinois and Market Street, you will have a birds eye view of Monument Circle and The Arts Garden. Enjoy a clean, spacious, and private stay while being close to all Indianapolis has to offer. Lucas Oil, the Indianapolis Convention Center, Gainbridge Fieldhouse, and popular restaurants are all in walking distance All art work on display are sourced from local artists.

Pink Lotus BnB: boho, romantic, stocked, *location

•Choose The Pink Lotus• •Romantic•Memorable•Relaxing•Uplifting• •Walkable to Convention Center, Stadium, Fieldhouse, + more •walkable city guide in listing photos. Historic Fletcher Place ~ Best Indy Neighborhood. Next to Amberson coffee, blocks from world renowned Milk Tooth, Irias Italian, Bluebeard, and much more. Convenient Reserved Parking Bedroom Theater, Putt-Putt, Fire Pit, BBQ Grill Pattern Magazine "Chaotic Luxury, December 2022

White River Retreat

Escape to a private retreat on the White River in Indianapolis! This custom-built home offers a peaceful, open-concept space with a stone fireplace, pool table, and jetted tub. Enjoy 12 acres of shared grounds with river access, kayaks, and fire pits. Perfect for a unique getaway, feeling worlds away yet close to everything. Ideal for couples or small groups seeking tranquility and adventure.