A river surrounded by dense forest with autumn foliage.

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.
Greenwood Old Town
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful area. The house was beautifully styled and maintained. They had issues with their cleaning company but nothing serious."
United States
Emil S.
The price is NZ$833
includes taxes & fees
16 Nov - 17 Nov
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
Greenwood
10.0 out of 10, Exceptional, (2 reviews)
"This was an amazing experience. Loved the movie room. Great for the kids. Plenty of room for 7 kids, 5 adults, and a baby. Gorgeous, large family table that we all could sit at together. The rooms are so cute and the beds are comfortable. Loved the outdoor space! This is where we spend the most time. Pool is perfect size and was so enjoyed. Fire pit to make s'mores. Plenty of outdoor seating. Nice hot tub to warm up after the pool. House itself is beautiful and large. Lots of space. Host is 100%...
United States
Kimberly C.
The price is NZ$1,114
includes taxes & fees
9 Nov - 10 Nov
Grandstand Gathering House: Pool, Theater, Gym

3. Winter stay Family Fun with game room & backyard

Winter stay Family Fun with game room & backyard
Windsong
9.6 out of 10, Exceptional, (8 reviews)
"In town for a softball tournament with family and it was a perfect stay for us! Everything was great!"
United States
Chelsey E.
The price is NZ$937
includes taxes & fees
3 Nov - 4 Nov
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
Greenwood Old Town
The price is NZ$1,279
includes taxes & fees
8 Nov - 9 Nov
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
Southern Homes
8.8 out of 10, Excellent, (10 reviews)
"Short stay… home is nice and in a decent location."
United States
Rob B.
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,
Edgewood
9.6 out of 10, Exceptional, (20 reviews)
"It was very comfortable and had everything I loved it!!"
United States
Misty M.
The price is NZ$480
includes taxes & fees
4 Nov - 5 Nov
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
Indianapolis
10.0 out of 10, Exceptional, (4 reviews)
"My daughters Sweet 16 birthday gathering at the Rosey Ranch was beautiful. We were surrounded by nature, the total experience was absolutely amazing! "
United States
Leticia B.
The price is NZ$482
includes taxes & fees
16 Nov - 17 Nov
Escape to the Rosy Rodeo Tiny Cabin

8. The Residences at CityWay

The Residences at CityWay
4.0 star property
Downtown Indianapolis
9.0 out of 10, Wonderful, (195 reviews)
"Location is amazing"
United States
Olivia
The price is NZ$428
includes taxes & fees
9 Nov - 10 Nov
The Residences at CityWay

9. CozySuites at East Washington

CozySuites at East Washington
4.0 star property
Downtown Indianapolis
8.0 out of 10, Very good, (52 reviews)
"I won’t be staying again."
United States
Ron
The price is NZ$353
includes taxes & fees
3 Nov - 4 Nov
CozySuites at East Washington

10. Historic Meadowdale Farm - Barn Stay in Rural Setting

Historic Meadowdale Farm - Barn Stay in Rural Setting
Indianapolis
10.0 out of 10, Exceptional, (183 reviews)
"Had a very relaxing stay, I will definitely be back again."
United States
Elizabeth H.
The price is NZ$324
includes taxes & fees
3 Dec - 4 Dec
Historic Meadowdale Farm - Barn Stay in Rural Setting

11. The Argyle on Mass Ave

The Argyle on Mass Ave
4.0 star property
Downtown Indianapolis
8.8 out of 10, Excellent, (229 reviews)
"Really perfect stay from check in to check out!"
United States
Lucy
The price is NZ$430
includes taxes & fees
17 Nov - 18 Nov
The Argyle on Mass Ave

12. Ruby’s Red Cabin Hot Tub Nature Horses Indy

Ruby’s Red Cabin Hot Tub Nature Horses Indy
Indianapolis
8.6 out of 10, Excellent, (14 reviews)
"One of the best places we ever stayed. Small, quiet, away from city noise. Perfect place to stay. The host was unbelievable and great."
United States
Paul
The price is NZ$557
includes taxes & fees
30 Nov - 1 Dec
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
Franklin
10.0 out of 10, Exceptional, (9 reviews)
"An outstanding place to relax and enjoy Franklin, Indiana. Great location and very comfortable accommodations, I would definitely stay here again!"
United States
Brian N.
The price is NZ$291
includes taxes & fees
3 Nov - 4 Nov
The Howdy Inn-Rustic Charm and Modern Comfort

14. Charming 2 Bedroom with in Home Gym

Charming 2 Bedroom with in Home Gym
3.0 star property
Indianapolis
8.4 out of 10, Very good, (9 reviews)
"Super clean with a garage that we didn't use."
United States
Randy
The price is NZ$606
includes taxes & fees
8 Nov - 9 Nov
Charming 2 Bedroom with in Home Gym

15. CozySuites - Penrose

CozySuites - Penrose
4.0 star property
Downtown Indianapolis
8.6 out of 10, Excellent, (32 reviews)
"Very nice and clean place I would definitely stay here again! Nice area as well plenty of food options walking distance"
United States
Zachia
The price is NZ$365
includes taxes & fees
9 Nov - 10 Nov
CozySuites - Penrose

16. Cowboy Bunkhouse hot tub/lake/farm/nature

Cowboy Bunkhouse hot tub/lake/farm/nature
Indianapolis
9.6 out of 10, Exceptional, (25 reviews)
"Minus the heat we enjoyed our stay. Wouldn’t mind going back in the fall."
United States
Lisa G.
The price is NZ$552
includes taxes & fees
3 Nov - 4 Nov
Cowboy Bunkhouse hot tub/lake/farm/nature

17. Block20 by CozySuites

Block20 by CozySuites
4.0 star property
Downtown Indianapolis
7.8 out of 10, Good, (104 reviews)
"Excellent location."
United States
Kelvin
The price is NZ$368
includes taxes & fees
9 Nov - 10 Nov
Block20 by CozySuites

18. The Onyx Cottage. Very cozy and private

The Onyx Cottage. Very cozy and private
Indianapolis
8.8 out of 10, Excellent, (46 reviews)
"Great place, close to downtown, safe area"
United States
Terri B.
The price is NZ$289
includes taxes & fees
15 Nov - 16 Nov
The Onyx Cottage. Very cozy and private

19. The Dragonfly- A Historic Gem with Hot Tub

The Dragonfly- A Historic Gem with Hot Tub
Franklin
10.0 out of 10, Exceptional, (42 reviews)
"Great space and was perfect for our trip. There were handy notes around to make everything easy and check in/out were smooth. Thank you for having us."
United States
Luke G.
The price is NZ$561
includes taxes & fees
3 Nov - 4 Nov
The Dragonfly- A Historic Gem with Hot Tub

20. The Block by CozySuites

The Block by CozySuites
4.0 star property
Downtown Indianapolis
7.6 out of 10, Good, (43 reviews)
"Every thing was great. Value for money. Controlled access . Extremely large 2bedroom, 2 full bath, full kitchen, large living room! Five star Extremely close to everything downtown"
United States
Steven
The price is NZ$352
includes taxes & fees
3 Nov - 4 Nov
The Block by CozySuites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenwood Hotel Reviews

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.

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals in Greenwood close to Otte Golf And Family Fun Center, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Greenwood. Make sure you have time to check out the parks and casinos during your trip.

What are some of the best holiday rentals that Greenwood has to offer?

Newly Rennovated Home next to Zoo and Downtown Stadiums: This holiday home rental outside of Greenwood is located in the city centre, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Greenwood?

Choose from 30 Expedia holiday rentals in Greenwood for a memorable holiday.

What can I see and do in Greenwood?

Family-friendly attractions include Otte Golf And Family Fun Center, whereas Doty Run Lake is a spot to enjoy the outdoors. While in the area, you can also visit popular places such as Lucas Oil Stadium and Gainbridge Fieldhouse.

What are holiday rentals like in Greenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenwood. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for small groups.