A forest with autumn-colored trees and a wooden fence.

Greenwood holiday lettings

We found 2,224 holiday rentals — enter your dates for availability

Discover a selection of 30 homes and other holiday rentals in Greenwood that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Greenwood

Showing deals for:12 Feb - 19 Feb

Luxury Modern Nearby Downtown Indy Escape: New Built. Game Room, 75” TVs

Dining

Mini Golf|Sauna|Hot Tub|Cinema|Large Group|BBQ

Outdoor spa retreat featuring a glowing Scandinavian-style sauna and relaxing hot tub—perfect for unwinding under the string lights at night.

Brown County Cabin near Nashville, Indiana

Terrace/patio

The WhiteHouse ! Your Private Oasis in Carmel

Living area

Spacious Fishers 3BR, Walk to Park + Fishers District

Private kitchen

The Sanctuary on Primrose- A beautiful award winning Bungalow in Broad Ripple!

View from the cozy fire pit looking at the 70” smart tv or beautiful pergola

Downtown Retreat 1 mile from city center!

Second living space with desk and sofa bed.

Winter stay Family Fun with game room & backyard

Exterior

Charming 4-bedroom house with WiFi in lovely Indianapolis

Dining

Casa Boho- Fire Pit, BBQ, B-ball hoop

Private kitchen

Downtown Indy • Walk to Stadiums • 4BR/3BA • Hot Tub • Game Room • Sleeps 13

Living area

HotTub~FirePit~Games~YogaNook~5 Mins to Downtown

Outdoor dining

Southern Indy Farmhouse ~ 4-beds, Game Room, & Pet Friendly

Terrace/patio

Historic Meadowdale Farm - Barn Stay in Rural Setting

Exterior

Indy Experience House / Movie Theater, Patio, Office, Private Parking

Living area

Hot Tub Log Cabin on 5 Wooded Acres. Private fishing pond.

Exterior detail

The Gathering Place "Upscale! Walkable! 5-Bedroom 4 Bathroom Downtown Indy"

Terrace/patio

Super Comfortable Home in the Heart of Speedway!!

Deck

Modern and Fun 4BR+ Pool Table in Fountain Square

A perfect spot for culinary adventurers to explore local flavors.

Private 3.5 acre Waterfront Cabin with Hot Tub, WiFi, Minutes from Nashville

Living area

Welcoming 3-bedroom house 2 blocks from UIndy& close to downtown

Living area

Big Beautiful House Close to Downtown Indianapolis with outdoor firepit

Front of house, plenty of public parking on street

Fantastic 4-bedroom house with AC in vibrant Indianapolis

Living area

Cozy Studio Retreat one block from Downtown Noblesville.

Room

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Find properties near top attractions in Greenwood

A park with a lake, trees, and a walking path.

1

Summerfield Park

Find the best place to stay - Greenwood

The Retreat - Private Pool-Spa-Firepit-Gameroom

Image of The Retreat - Private Pool-Spa-Firepit-Gameroom

Premier Host

Sleeps 12 · 4 bedrooms · 2+ bathrooms

NEW Retreat 4-bedroom Indianapolis Dreamhouse with Hot tub & Pets ok

Image of NEW Retreat 4-bedroom Indianapolis Dreamhouse with Hot tub & Pets ok

Premier Host

Sleeps 12 · 4 bedrooms · 3 bathrooms

OliveBranch-LuxeDesigner Home-Spa-Firepit-GameZone

Image of OliveBranch-LuxeDesigner Home-Spa-Firepit-GameZone

Premier Host

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Charming 3 BR in a quiet and friendly neighborhood

Image of Charming 3 BR in a quiet and friendly neighborhood

Premier Host

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Greenwood Family Bungalow - Parking

Image of Greenwood Family Bungalow - Parking

Premier Host

Sleeps 4 · 2 bedrooms · 1 bathroom

Grandstand Gathering House: Pool, Theater, Gym

Image of Grandstand Gathering House: Pool, Theater, Gym

Sleeps 20 · 7 bedrooms · 3+ bathrooms

Frequently Asked Questions

What is the best area to stay in Greenwood when booking a holiday rental?

When considering the best area to stay in Greenwood, Indiana for a holiday rental, the charming neighbourhood of Old Town Greenwood stands out. This area is rich in history and offers a delightful atmosphere with a mix of quaint shops and restaurants. It's a wonderful spot for those who appreciate a vibrant community feel. One of the top attractions nearby is the Greenwood Community Centre, which often hosts events and activities, making it a hub of local culture. Additionally, the charming Old Town Square provides a picturesque setting to explore local boutiques and enjoy a meal at one of the inviting eateries.

Another excellent option is the area around Smith Valley, which boasts a more suburban feel while still being conveniently located near parks and recreational facilities. The nearby Craig Park is a lovely place to unwind and enjoy nature, featuring walking trails, picnic areas, and a playground, making it suitable for families. Staying in Smith Valley offers a balance of tranquillity and accessibility to Greenwood's amenities.

How much does it cost to rent a holiday home in Greenwood?

Prices for holiday rentals in Greenwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Greenwood to more spacious homes. To get the best value, book early and take advantage of Vrbo’s free rewards program.

Are there any discounts for Greenwood holiday house rentals?

You can find great discounts on house rentals in Greenwood on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

What is the most popular type of holiday rental accomodation in Greenwood?

In Greenwood, holiday houses are the most popular type of holiday rental, with around 60 available throughout the area. These homes typically offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Many are situated in family-friendly neighbourhoods, providing a comfortable base for exploring local attractions. Additionally, there are several apartments and villas to choose from, which offer more compact living options with the convenience of self-catering amenities.

Are there any family house rentals in Greenwood?

In Greenwood, Indiana, there are numerous family-friendly house rentals available, with about 15 options to choose from. This charming city offers a variety of homes that cater to families, featuring spacious living areas and fully equipped kitchens superb for preparing family meals. Many properties also include outdoor spaces, where children can enjoy playing, along with amenities like Wi-Fi and air conditioning for added comfort.

Visitors can explore nearby attractions such as the Greenwood Park Mall for shopping and dining, or enjoy the great outdoors at Craig Park, which boasts playgrounds and walking trails.

Can I rent a holiday home with a pool or hot tub in Greenwood?

In Greenwood, Indiana, there are several holiday homes available for rent that feature pools and hot tubs. This charming suburb, located just south of Indianapolis, offers a variety of properties suitable for families or groups seeking a relaxing getaway. Many rentals come with private pools and hot tubs, allowing guests to enjoy leisure time right at home.

Travellers can expect amenities such as spacious living areas, fully equipped kitchens for self-catering, and outdoor spaces superb for barbecues or lounging by the pool. The area is also conveniently located near local parks and recreational facilities, providing additional options for outdoor activities.

Can I find long-stay holiday rentals in Greenwood?

A long-stay holiday rental in Greenwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there pet-friendly house rentals in Greenwood?

In Greenwood, Indiana, there are several pet-friendly house rentals available for those looking to enjoy a getaway with their furry companions. The area offers a mix of charming suburban homes that typically feature spacious layouts, fully equipped kitchens, and outdoor spaces such as fenced yards or patios, making them ideal for families or groups travelling with pets. Many of these properties are conveniently located near local parks, providing ample opportunities for walks and outdoor play with your pets.

Greenwood is also close to the tranquil Freedom Park, which features walking trails, picnic areas, and a pond, superb for a day out with your dog. The friendly neighbourhood atmosphere and nearby amenities, including shops and restaurants, further enhance the experience for visitors.

Are there any remote work holiday rentals in Greenwood?

In Greenwood, Indiana, remote work holiday rentals are quite abundant, with around 69 options available for those seeking a productive getaway. Many properties offer essential amenities for remote work, including complimentary Wi-Fi in both rooms and public areas, as well as designated workspaces and desks within the units. This makes it easy for travellers to stay connected and focused during their stay.

The area itself is conveniently located near various points of interest, such as parks and shopping centres, providing a great blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

Are there any Greenwood holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Greenwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the “Parking available” filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

What are popular rental amenities in Greenwood?

In Greenwood, popular holiday rentals typically feature a variety of amenities that enhance the stay for visitors. Most accommodations come equipped with kitchens, allowing guests to prepare their own meals and enjoy a home-like experience. Onsite parking is commonly available, making it convenient for those travelling with vehicles. Additionally, many rentals provide coffee and tea makers for that morning boost, and outdoor spaces such as decks or patios are often included, great for relaxing outside after a day of exploring the local attractions.

When is the best time to visit Greenwood for a holiday rental?

The most popular time to visit Greenwood is during the peak season from May to July, when the area comes alive with vibrant activities and warm weather. This period is ideal for families and outdoor enthusiasts who enjoy exploring local parks, attending community events, and participating in outdoor sports. With temperatures typically ranging from 20 to 30 degrees Celsius, visitors can comfortably enjoy the beautiful surroundings.

July stands out as the busiest month, offering a lively option with numerous festivals and events, such as the renowned Freedom Festival. This is a wonderful opportunity to immerse yourself in local culture, savour delicious food, and enjoy the energetic vibe of the community.

If you're looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it provides a great experience with festive decorations and holiday events that bring a different charm to Greenwood. You can enjoy quieter streets, local shopping, and the warmth of community gatherings during this time.

Ultimately, the best time to book a holiday rental in Greenwood depends on your preferences—whether you fancy the bustling summer months filled with activities or the tranquil, festive spirit of December.

How early should I book a Greenwood holiday rental?

Book your Greenwood holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in Greenwood?

In Greenwood, Indiana, visitors can enjoy a range of attractions that showcase the city's charm. The Greenwood Park Mall is a central hub for shopping and dining, offering a variety of stores and eateries, making it a popular destination for both locals and tourists. Nearby, the Old Town Greenwood area features quaint shops and restaurants, superb for a leisurely stroll.

For those interested in outdoor activities, the city boasts several parks, including Craig Park, which offers walking trails, sports facilities, and picnic areas. The park is a great spot for families to relax and enjoy the outdoors. Additionally, the Greenwood Community Centre often hosts events and activities that cater to residents and visitors alike.

The city is also home to the Greenwood Public Library, which offers a range of programs and resources for all ages, making it a great place for educational pursuits.

Can I change or cancel my Greenwood home rental booking on Vrbo?

To find Greenwood holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

Are all fees included in the Greenwood holiday rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

What is VrboCare™ and how does it work?

Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

What can I expect from Vrbo customer service and VrboCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

Can I plan a group trip on Vrbo?

Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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