A river surrounded by dense forest with autumn foliage.

Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Greenwood vacation rentals

A patio area with a fire pit, outdoor seating, and string lights.

1. 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.
$548 nightly
The price is $613
Oct 7 - Oct 8
Total with taxes and fees
Grandstand Gathering House: Pool, Theater, Gym
A two-story house with a garage, a well-maintained lawn, and a large tree in the background.

2. Winter stay Family Fun with game room & backyard

Winter stay Family Fun with game room & backyard
Windsong
10.0 out of 10, Exceptional, (7 reviews)
"Was just as described and lots of little extras. Would stay here again. "
United States
Ryan K.
$485 nightly
The price is $543
Sep 30 - Oct 1
Total with taxes and fees
Winter stay Family Fun with game room & backyard
A two-story house with a balcony, a porch, and a well-lit driveway.

3. Historic Meadowdale Farm - Barn Stay in Rural Setting

Historic Meadowdale Farm - Barn Stay in Rural Setting
Indianapolis
10.0 out of 10, Exceptional, (179 reviews)
"Had a very relaxing stay, I will definitely be back again."
United States
Elizabeth H.
$165 nightly
The price is $185
Sep 30 - Oct 1
Total with taxes and fees
Historic Meadowdale Farm - Barn Stay in Rural Setting
A cozy room with a large flat-screen TV, comfortable seating, popcorn, and a decorative vase.

4. Movie Theater & Game Room Sleeps 8 Indianapolis

Movie Theater & Game Room Sleeps 8 Indianapolis
Southern Homes
8.8 out of 10, Excellent, (10 reviews)
"Short stay… home is nice and in a decent location."
United States
Rob B.
$339 nightly
The price is $397
Oct 11 - Oct 12
Total with taxes and fees
Movie Theater & Game Room Sleeps 8 Indianapolis
A spacious living area with a dining table, a ceiling fan, and a view of the outdoors.

5. 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, (18 reviews)
"Was a very cozy house and the bed was extremely comfortable. "
United States
Jessica G.
$209 nightly
The price is $245
Sep 30 - Oct 1
Total with taxes and fees
Cozy 2-bedroom house in charming Indianapolis with AC, Close to downtown,
A living room with a sofa, ottoman, coffee table, TV, and a rug.

6. The Dragonfly- A Historic Gem COMPLETELY Restored!

The Dragonfly- A Historic Gem COMPLETELY Restored!
Franklin
10.0 out of 10, Exceptional, (40 reviews)
"Well run rental in quaint town. Within walking distance to downtown which includes old theater, square and restaurants/bars."
United States
Paula C.
$283 nightly
The price is $317
Oct 18 - Oct 19
Total with taxes and fees
The Dragonfly- A Historic Gem COMPLETELY Restored!
A kitchen with green cabinets, a stainless steel stove, a microwave, a sink, and a window with a blue valance.

7. Charming 2-bedroom guest house with WiFi, AC in Franklin

Charming 2-bedroom guest house with WiFi, AC in Franklin
Franklin
9.2 out of 10, Wonderful, (19 reviews)
"Great stay!"
United States
Bruce H.
$223 nightly
The price is $250
Oct 4 - Oct 5
Total with taxes and fees
Charming 2-bedroom guest house with WiFi, AC in Franklin
A covered patio with a wooden table, chairs, and a blue sofa with cushions.

8. Modern-Sunroom-15min to DwnTwn-Grps-Kids-Firepit

Modern-Sunroom-15min to DwnTwn-Grps-Kids-Firepit
Indianapolis
9.4 out of 10, Exceptional, (54 reviews)
"Great place for families. Big yard, ample parking. Games for the kids. Wonderful screened porch, plenty of room to spread out and extra sleeping areas if needed. Owner is responsive to any need."
United States
Cheryl
$321 nightly
The price is $375
Oct 1 - Oct 2
Total with taxes and fees
Modern-Sunroom-15min to DwnTwn-Grps-Kids-Firepit
A living room with a white sofa, a wooden coffee table, and a red storage box.

9. The Howdy Inn-Rustic Charm and Modern Comfort

The Howdy Inn-Rustic Charm and Modern Comfort
Franklin
10.0 out of 10, Exceptional, (7 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.
$164 nightly
The price is $184
Oct 4 - Oct 5
Total with taxes and fees
The Howdy Inn-Rustic Charm and Modern Comfort
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with balconies.

10. The Residences at CityWay

The Residences at CityWay
4.0 star property
Downtown Indianapolis
9.0 out of 10, Wonderful, (189 reviews)
"Excellent location for going to Gainbridge Fieldhouse. The apartment was very nice and spotless, the building hallways & stairwells could use a cleaning however."
United States
Jennifer
$251 nightly
The price is $263
Oct 8 - Oct 9
Total with taxes and fees
The Residences at CityWay
A neatly made bed with patterned bedding, two bedside lamps, and a window with blinds.

11. The Onyx Cottage. Very cozy and private

The Onyx Cottage. Very cozy and private
Indianapolis
8.8 out of 10, Excellent, (45 reviews)
"Great place, close to downtown, safe area"
United States
Terri B.
$147 nightly
The price is $172
Sep 30 - Oct 1
Total with taxes and fees
The Onyx Cottage. Very cozy and private
A two-story house with a front porch, steps, and a small garden.

12. Mable’s Place at Emerson Heights. Near Irvington, Fountain Square and downtown.

Mable’s Place at Emerson Heights. Near Irvington, Fountain Square and downtown.
Near Eastside
10.0 out of 10, Exceptional, (52 reviews)
"Nice location for our event at Beech Grove High School. Would stay again if in the area and needing a place to stay! "
United States
Caitlin G.
$192 nightly
The price is $225
Oct 6 - Oct 7
Total with taxes and fees
Mable’s Place at Emerson Heights. Near Irvington, Fountain Square and downtown.
A spacious living area with a large window, a sofa, a coffee table, a TV, and a dining table with chairs.

13. CozySuites - Penrose

CozySuites - Penrose
4.0 star property
Downtown Indianapolis
8.6 out of 10, Excellent, (25 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
$165 nightly
The price is $194
Oct 6 - Oct 7
Total with taxes and fees
CozySuites - Penrose
A modern kitchen with a central island, bar stools, stainless steel appliances, and a high ceiling with exposed ductwork.

14. Black house stays sleeps 10

Black house stays sleeps 10
Fountain Square
10.0 out of 10, Exceptional, (15 reviews)
"This was a excellent and relaxing venue!"
United States
Helen O.
$348 nightly
The price is $410
Sep 30 - Oct 1
Total with taxes and fees
Black house stays sleeps 10
A room with a bed, a desk, and a wardrobe. There are dumbbells on the floor.

15. Charming 2 Bedroom with in Home Gym

Charming 2 Bedroom with in Home Gym
3.0 star property
Indianapolis
8.0 out of 10, Very good, (8 reviews)
"Super clean with a garage that we didn't use."
United States
Randy
$302 nightly
The price is $353
Oct 2 - Oct 3
Total with taxes and fees
Charming 2 Bedroom with in Home Gym
Full Kitchen Fully Stocked

16. Historic Downtown Indy Neighborhood Calvary

Historic Downtown Indy Neighborhood Calvary
Fountain Square
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful home in a great location. We came for a basketball game and it was the perfect place. Hot tub was perfect! Would absolutely stay here again."
United States
Lori C.
$333 nightly
The price is $393
Sep 30 - Oct 1
Total with taxes and fees
Historic Downtown Indy Neighborhood Calvary
A house with a porch, a mailbox, and a flower bed with various flowers.

17. 2 Bedroom with Finished Basement Duplex Close to Downtown Indianapolis

2 Bedroom with Finished Basement Duplex Close to Downtown Indianapolis
Near Eastside
9.0 out of 10, Wonderful, (46 reviews)
"This is a neat property that has undergone some great remodeling, which is on going. Secure access, good communication with Steve. Easy to get Amazon and InstaCart deliveries. Great location right off I-70."
United States
David M.
$208 nightly
The price is $244
Sep 30 - Oct 1
Total with taxes and fees
2 Bedroom with Finished Basement Duplex Close to Downtown Indianapolis
A wooden staircase with a brick wall on one side and a white panel on the other.

18. Magnificent 2 Bedroom, Loft Close to Downtown Duplex

Magnificent 2 Bedroom, Loft Close to Downtown Duplex
Near Eastside
9.2 out of 10, Wonderful, (46 reviews)
"Very nice place"
United States
Marty R.
$246 nightly
The price is $287
Sep 30 - Oct 1
Total with taxes and fees
Magnificent 2 Bedroom, Loft Close to Downtown Duplex
A compact kitchen with white cabinets, a microwave, a coffee maker, and a dishwasher.

19. The Argyle on Mass Ave

The Argyle on Mass Ave
4.0 star property
Downtown Indianapolis
8.8 out of 10, Excellent, (218 reviews)
"Great place to stay in an awesome area! Just be aware the windows/walls are very thin so you can hear all the street traffic and pedestrian noise."
Canada
Kassandra
$216 nightly
The price is $227
Oct 4 - Oct 5
Total with taxes and fees
The Argyle on Mass Ave
A rooftop terrace with outdoor seating, a view of a historic tower, and modern buildings in the background.

20. CozySuites at Block20

CozySuites at Block20
4.0 star property
Downtown Indianapolis
7.8 out of 10, Good, (92 reviews)
"The check in was very tricky with four codes needed but that made it very secure"
United States
Debra
$175 nightly
The price is $206
Oct 5 - Oct 6
Total with taxes and fees
CozySuites at Block20
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

The Fontana Hotel

The Fontana Hotel

8/10 Good
"Right value for the price."
Errol 2-night trip
Posted 1 hour ago
The Fontana Hotel

Find out more about Greenwood

Everything you need to know about Greenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Greenwood?

Yes, we offer vacation rentals in Greenwood close to Otte Golf And Family Fun Center, or you can choose a more secluded option if you'd like a relaxing place to 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 vacation rentals that Greenwood has to offer?

Newly Rennovated Home next to Zoo and Downtown Stadiums: This vacation home rental outside of Greenwood is located in the city center 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 you can cook with friends or family.

How many vacation rentals are there in Greenwood?

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

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 like Lucas Oil Stadium and Gainbridge Fieldhouse.

What are vacation rentals like in Greenwood?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Greenwood. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family gatherings.