
Greenwood Holiday Rentals
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Our top choices for Greenwood holiday rentals

1. Peaceful 3-bedroom 2 full bath house finished basement AC in charming Greenwood.
Peaceful 3-bedroom 2 full bath house finished basement AC in charming Greenwood.
2. Grandstand Gathering House: Pool, Theater, Gym
Grandstand Gathering House: Pool, Theater, Gym
3. Winter stay Family Fun with game room & backyard
Winter stay Family Fun with game room & backyard
4. Courthouse in walkable Historic Greenwood-Downtown Indianapolis 20 min, sleep 12
Courthouse in walkable Historic Greenwood-Downtown Indianapolis 20 min, sleep 12
5. Movie Theater & Game Room - Sleeps 8 - Indianapolis Vacation Home
Movie Theater & Game Room - Sleeps 8 - Indianapolis Vacation Home
6. Cozy 2-bedroom house in charming Indianapolis with AC, Close to downtown,
Cozy 2-bedroom house in charming Indianapolis with AC, Close to downtown,
7. Escape to the Rosy Rodeo Tiny Cabin
Escape to the Rosy Rodeo Tiny Cabin
8. The Residences at CityWay
The Residences at CityWay
9. CozySuites at East Washington
CozySuites at East Washington
10. Historic Meadowdale Farm - Barn Stay in Rural Setting
Historic Meadowdale Farm - Barn Stay in Rural Setting
11. The Argyle on Mass Ave
The Argyle on Mass Ave
12. Ruby’s Red Cabin Hot Tub Nature Horses Indy
Ruby’s Red Cabin Hot Tub Nature Horses Indy
13. The Howdy Inn-Rustic Charm and Modern Comfort
The Howdy Inn-Rustic Charm and Modern Comfort
14. Charming 2 Bedroom with in Home Gym
Charming 2 Bedroom with in Home Gym
15. CozySuites - Penrose
CozySuites - Penrose
16. Cowboy Bunkhouse hot tub/lake/farm/nature
Cowboy Bunkhouse hot tub/lake/farm/nature
17. Block20 by CozySuites
Block20 by CozySuites
18. The Onyx Cottage. Very cozy and private
The Onyx Cottage. Very cozy and private
19. The Dragonfly- A Historic Gem with Hot Tub
The Dragonfly- A Historic Gem with Hot Tub
20. The Block by CozySuites
The Block by CozySuitesFind holiday rentals that suit your style
Top Greenwood Hotel Reviews

Candlewood Suites Indianapolis Downtown Medical District by IHG
Find out more about Greenwood
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greenwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Greenwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Greenwood. Seeing all the best attractions is bound to make you fall in love with Greenwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Greenwood short-term rentals, that won’t be hard to do.

































































