Holiday houses in Greenfield

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.

Quaint & Walking Distance to All The Fun!

Our place is recently renovated and walking distance to all of the amazing amenities Greenfield has to offer. Within half a mile of our place you will find beautiful Riley Park, a FREE community Splash Pad, a just renovated public pool with waterslides, the historic Old Log Jail Museum, the famous James Whitcomb Riley Boyhood Home and Museum, and all of the locally owned eateries and boutiques of downtown Greenfield. Start or end your days with a walk on our serene 5.6 mile paved Pennsy Trail.

Updated Historic Home, in the Heart of Greenfield

A one-of-a-kind historic gem located three blocks from Downtown Greenfield on Main Street and only a 35-minute drive to downtown Indianapolis. Enjoy the entire downstairs of this completely upgraded late 1800's wooden frame home featuring all original wood flooring and beautiful antique furniture pieces. Filled with modern luxuries; including 3 flat screen tv's with streaming services included, an upgraded 8 burner gas stove, dishwasher, full-size washer and dryer, and outdoor barbecue grill.

The Rosie Roots - Cozy House & Pet Friendly

Welcome to our cozy & pet friendly 3 bedroom 1 bathroom house located in the heart of Greenfield, within 5 min to local shops & dinning and I-70. Downtown Indianapolis is a short 25-minute drive away, you'll have easy access to all the city's top attractions, including the Gainbridge Fieldhouse, Lucas Oil Stadium and many more. Our home is the perfect choice for guests who want to be close to all the action of the city while still enjoying the comfort and convenience of a charming small town.

Modern Carriage House Indianapolis

Welcome to our charming carriage house in the heart of Indianapolis! Just minutes from the Convention Center, Lucas Oil Stadium, Gainbridge Fieldhouse, Bottleworks District, and Mass Ave, our location is perfect for exploring. Enjoy modern comforts in a historic setting with a cozy living area, a fully equipped kitchen, comfortable bedrooms, a modern bathroom, one garage space, free coffee, fast wifi, and high-quality furniture for a comfortable stay. Book now for an unforgettable experience

Tall, Dark and Handsome 2BR in historic Irvington

Situated in the heart of Irvington’s historic district, Sawyer Crossing features striking industrial design, outfitted with quality leather furnishings and thoughtful attention to detail. An updated duplex with two bedrooms and one bathroom, the home is set up with a generously stocked kitchen, so you have the option to cook meals and brew fresh coffee during your stay. Stroll the brick lined streets of Irvington and discover the local shops, restaurants, and coffee houses.

Studio by Falls Park

Welcome to the Studio by Falls Park. This is a family-friendly studio apartment with a separate entrance. You are within walking distance to several good restaurants and the local drinking hole (The Wine Stable), Falls Park, walking trails. Located 10 minutes off I-69, and 20 minutes North of Indianapolis. Harrah’s casino is 15 minutes North on I-69. Studio has shower/bath, 1 queen bed, a full size futon, queen size blowup mattress and kitchen.

Greenfield CountryCottage-minutes to downtown Indy

Beautiful, relaxing country cottage room is a perfect place to stay for your business trip or vacation. We provide clean and comfortable furnishings, along with a kitchenette and coffee bar. You will have total privacy, including a private driveway and entrance. Relax on the balcony with your morning coffee or after a busy day. Our room is located on a 2nd story with a private stairway to the entrance. Special discount on stays 3 days or more!

Walk 2 Convention Ctr | Stunning Views | Penthouse

WE DO NOT ACCEPT LOCAL BOOKINGS Welcome to Suite Spot's premier penthouse Airbnb, nestled within "The Block" in the heart of vibrant Downtown Indianapolis, offering unparalleled luxury and convenience. Situated next to the iconic Arts Garden, Monument Circle, and the Convention Center. Our penthouse Airbnb offers unrivaled access to the city's finest attractions, including world-class dining, shopping, entertainment, and cultural venues!

La Cochera Indy East - No Cleaning Fee!

Contemporary, clean carriage house on a large East Indianapolis property. Private keypad entrance with easy self check-in and on-site parking for up to two cars. Comfortably sleeps the whole family with a king bed and a stylish queen-size sofa bed. Important details: • No parties or events • Local guests require prior approval • Early check-in available for $35 (when possible) • $20–$40 linen fee for use of sofa bed

The Indy Nook

Brand-new in 2025, this cozy 1 bed, 1 bath guest home sleeps up to 3 and has all the comforts of home. Enjoy a fully equipped kitchen, fast Wi-Fi, smart TV, and in-unit laundry. The private, fully fenced yard is perfect for relaxing. Just 2 minutes from the I-70 on-ramp, you'll have quick access to local shops, dining, and attractions. Ideal for short or extended stays—your perfect home base awaits!

Cobb Cabin

Take it easy at this unique and tranquil getaway. Quiet and relaxing 1 bedroom studio home with king bed. Only 18 minutes from downtown. Couch pulls out for added comfort, leg room and sleeping area. There is a fold out single cot and a fold out queen mattress available. Full kitchen, smart tv, washer/dryer, private security system and all the basics are all with this secluded home.