Luxury Vacation Rentals in Greenwood

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 2 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Greenwood

Home in Greenwood

4 bedrooms•3 baths

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New

Home in Greenwood

5 bedrooms•4 baths

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Welcome to Greenwood

Explore our elevated collection of luxury vacation rentals in Greenwood, Indiana, where hotel-grade consistency meets the ease of a private home. Every stay is beautifully designed, spotless, and supported by 24/7 concierge, so you can settle in without a second thought.

Choose from contemporary suburban homes with open-concept living, multiple bedrooms, and generous natural light. Expect ultra fast WiFi, fully equipped kitchens, smart entertainment, and crisp linens, along with thoughtful touches like dedicated workspaces and attached garages for effortless arrivals.

With Wander, you get the reliability of a luxury hotel and the privacy you prefer, turning your Greenwood stay into a seamless, stress-free retreat.

Available soon in Greenwood

Home in Greenwood

4 bedrooms•3 baths

•

New

All homes in Greenwood

Home in Greenwood

4 bedrooms•3 baths

•

New

Home in Greenwood

5 bedrooms•4 baths

•

View all homes

Highlights in Greenwood

Experience the perfect blend of small-town charm and modern convenience with premier shopping, family-friendly water parks, and scenic local wineries.

Greenwood Park Mall

Freedom Springs Greenwood Aquatics Park

Old Town Greenwood

Mallow Run Winery

Craig Park

Valle Vista Golf Club

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Greenwood

Outdoor dining area (1)

Other popular amenities & vacation types in Greenwood

Family vacation rentals in Greenwood

Large group vacation rentals in Greenwood

Pet-friendly vacation rentals in Greenwood

Hot tub vacation rentals in Greenwood

Private pool vacation rentals in Greenwood

Discover more of Greenwood

Set just south of Indianapolis, Greenwood blends small-town warmth with modern convenience. Tree-lined neighborhoods lead to vibrant parks, greenways, and community spaces that make it easy to slow down without sacrificing access.

Spend sunny days at Freedom Springs Greenwood Aquatics Park, wander the reimagined Old City Park with its striking play tower and creekside paths, or tee off at nearby Smock Golf Course. Shop and people-watch at Greenwood Park Mall, then explore local coffee roasters and taprooms around Main Street.

The balance of calm and connection makes this a smart base for any itinerary, which is why Wander’s luxury vacation rentals in Greenwood, Indiana are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Greenwood

Why should I book a Wander in Greenwood over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Greenwood delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Greenwood?

Some of our most popular vacation rentals in Greenwood include Greenwood Gem | Pool, Hot Tub, Arcade | S10, Luxury 5BR Sleeps 20 | Dome, Pool, Sauna | Pets, and Greenwood Gem | Pool, Hot Tub, Arcade | S10. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Greenwood?

Wander offers 2 vacation rentals in Greenwood, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Greenwood?

You can check-in to Wander vacation rentals in Greenwood after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Greenwood have WiFi access?

Yes. Every Wander home in Greenwood has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.