Pet-friendly holiday rentals in Greenwood

#IndyCozyCottage | Historic Cottage Near Downtown

Hello, Fellow Traveler! Welcome to our cozy historic Indy cottage in a quiet neighborhood retreat just minutes from downtown. Enjoy coffee on the porch, a fenced yard for pets, and easy access to Mass Ave, Bottleworks, and Lucas Oil Stadium. Thoughtfully updated for comfort and style while keeping its original charm! This quaint home features a king bedroom with walk-in closet, updated and stocked kitchen, secondary flex bedroom/office, and two-car garage. Perfect for your next Indy adventure!

Walkability · Outdoor spaces · Cleanliness

Cheerful & cozy farmhouse 2 bedroom home

Kick back and relax in this stylish space that is right down the street from Old Greenwood & less than 20 mins to Downtown Indianapolis. This tastefully updated home exudes "peaceful and cozy" w/ 2 bedrooms w/ brand new luxury king sized mattresses, 1.5 baths w/ walk-in tile shower, charming living room w/55" TV, Fiber internet, front load washer and dryer, dining table for 4+ bar seating, and a tranquil backyard space that is fully fenced, (dog friendly for an extra $75 cleaning fee, NO CATS).

Outdoor spaces · Walkability · Value

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.

Walkability · Pets · Parking

Charming 2-bedroom home on Greenwood bike trail

Cozy up with the whole family in this lovely two-bedroom, one-bathroom home. This stay includes a king and queen bed, with a TV in each bedroom. Grab a bite to eat at one of the many local restaurants or whip up your own meal in the fully-stocked kitchen. A dishwasher, microwave, air fryer, Keurig, pet bowls, and toddler dishes/utensils are included. Be sure to take advantage of the fenced-in backyard, fire pit, and gas grill. You will find a treadmill, elliptical, and weights in the garage.

Pets · Walkability · Decor

Cozy Cottage 14 mi. S of Indy In Bargersville, IN

Relax and unwind in this spacious three bedroom, one bath ranch home situated on one acre. The house is on about 1/2 the acre. The house is situated in Bargersville, Indiana in Johnson County, IN on the southern edge of Greenwood located in Center Grove Area. The garage area is not accessible. Vivint Home Security system with doorbell camera. I will email your unique code once you complete reservation. Central a/c & heat. Bedroom off kitchen has window a/c. We live about 1/4 mile away.

Pets · Walkability · Layout

Cozy Downtown Retreat - Walkable to Everything

A cozy, updated craftsman home in the heart of downtown Greenwood that we affectionately call "The Pearl". Walkable to restaurants, shops, parks, and a convenience store. Only a 20-min drive to downtown Indy, Lucas Oil Stadium, Indianapolis Zoo, Fountain Square, and the convention center. It's a great hub for your greater Indianapolis adventure! It's a great space for families, small groups, and co-workers with an open layout that allows everyone to gather together or spread out.

Walkability · Outdoor spaces · Decor

Lofty Cottage

This unique place has a style all its own. Walking distance to Lucas Oil Stadium this renovated cottage has 1 bedroom plus a king size bed in the loft, accessed via ships ladder. Modern kitchen with waterfall quartzite peninsula counters. Patio out front and a backyard with a grill and seating area. Plus free wifi & coffee. A block away from Iozzos, Greek Islands and Shapiro's Delicatessen, 4 minutes from award winning restaurants like Bluebeard, Milktooth and St. Elmo's Steakhouse.

Walkability · Pets · Sleep quality

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.

Pets · Walkability · Value

*Home away from home, 20 min. to Indy downtown

Enjoy your home away from home in a quiet neighborhood just minutes from all the attractions of downtown Indy. 5 minutes from the highway with lots of restaurants and stores nearby. 15 minutes to the Lucas Oil Stadium, 20 minutes to the Convention Center, Indianapolis Zoo, and White River State Park. 25 minutes to the Motor Speedway. Home is fresh, comfortable, and stylish. Stocked kitchen, fully fenced backyard with a fire pit and a picnic table.

Outdoor spaces · Walkability · Comfort

Fountain Square Luxe w/ Hot Tub

Beautiful freshly remodeled home in the vibrant and fun historic Fountain Square neighborhood very close to downtown Indy and Fountain Square nightlife. Super comfortable home with leather sofa and new everything! Walk out oversized deck from master suite with relaxing hottub. Full laundry on main floor as well as two brand new full baths covered in stylish tile. Feel as comfortable as at home while away.

Walkability · Pets · Indoor spaces

Private, one car garage, hot coffee

Welcome to Robin's Nest, my cozy, modern, open-concept home in Indy! This inviting space includes 2 bedrooms, 1 bathroom, and 2 queen beds. Enjoy amenities such as a coffee bar, fire pit, and workstation. Let your fur babies run free in my fully fenced-in yard. You’re in close proximity to Lucas Oil, the Convention Center, and Gainbridge Fieldhouse, Murat, and many major hospitals are in a 10 mile radius.

Pets · Outdoor spaces · Indoor spaces

Historic Meadowdale Farm

Relax at this peaceful historic farm stay! Located in our pole barn built in 2023, this private unit sleeps 4 (1 bed/1 bath) just 15–20 mins from city life and shopping. Step into your dog-friendly, 1/4-acre fenced yard featuring a covered outdoor dining area, porch swing, and a cozy firepit for evenings under the stars. The perfect rural retreat with plenty of room to unwind!

Outdoor spaces · Pets · Nearby