Discover Your Perfect Greendale Vacation Homes

Best Vacation Homes in Greendale

Cottage
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like-icon9.8
Exceptional
(171 Reviews)
2 Bedrooms 1 Bath 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $167/Night 7 Nights - US $1,167
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House
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like-icon8.0
Excellent
(5 Reviews)
3 Bedrooms 2 Baths 7 Guests 1323.96 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
More amenities
US $290/Night 7 Nights - US $2,028
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Hotel
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like-icon8.8
Fabulous
(1001 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Breakfast
    Breakfast
More amenities
US $118/Night 7 Nights - US $826
Apartment
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like-icon10.0
Exceptional
(18 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $199/Night 7 Nights - US $1,394
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House
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2 Bedrooms 2 Baths 4 Guests 1496.18 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
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US $261/Night 7 Nights - US $1,827
House
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like-icon10.0
Exceptional
(5 Reviews)
2 Bedrooms 2 Baths 5 Guests 2200 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $357/Night 7 Nights - US $2,500
House
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like-icon10.0
Exceptional
(4 Reviews)
2 Bedrooms 2 Baths 4 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $201/Night 7 Nights - US $1,404
House
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like-icon9.8
Exceptional
(38 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $296/Night 7 Nights - US $2,074

Greendale Luxury Rentals

House
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like-icon10.0
Exceptional
(17 Reviews)
4 Bedrooms 4 Baths 12 Guests 4000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $531/Night 7 Nights - US $3,716
House
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like-icon10.0
Exceptional
(88 Reviews)
6 Bedrooms 3 Baths 14 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $379/Night 7 Nights - US $2,655
House
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like-icon10.0
Exceptional
(17 Reviews)
3 Bedrooms 2 Baths 7 Guests 1320 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $310/Night 7 Nights - US $2,167
House
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like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 1 Bath 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $298/Night 7 Nights - US $2,087
New
House
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1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $248/Night 7 Nights - US $1,733
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House
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1 Bedroom 2 Baths 6 Guests 1808.34 ft²
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
More amenities
US $222/Night 7 Nights - US $1,557
House
Map-icon
like-icon10.0
Exceptional
(88 Reviews)
4 Bedrooms 2 Baths 10 Guests 1250 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $213/Night 7 Nights - US $1,494
House
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2 Bedrooms 1 Bath 7 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $190/Night 7 Nights - US $1,333

Greendale Pet Friendly Vacation Rentals

Apartment
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like-icon9.2
Exceptional
(17 Reviews)
2 Bedrooms 1 Bath 4 Guests 1040 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $140/Night 7 Nights - US $980
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Hotel
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like-icon8.6
Fabulous
(244 Reviews)
5 Baths 360.59 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $118/Night 7 Nights - US $827
Hotel
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like-icon8.2
Excellent
(924 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $77/Night 7 Nights - US $541
House
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2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $224/Night 7 Nights - US $1,565
Hotel
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like-icon7.6
Very Good
(422 Reviews)
6 Baths 331.88 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $73/Night 7 Nights - US $509
House
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2 Bedrooms 1 Bath 8 Guests 850 ft²
  • View
    View
  • Pet Friendly
    Pet Friendly
More amenities
US $154/Night 7 Nights - US $1,078
House
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like-icon9.4
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $279/Night 7 Nights - US $1,953
House
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like-icon10.0
Exceptional
(8 Reviews)
3 Bedrooms 2 Baths 7 Guests
  • Hot Tub
    Hot Tub
  • Skiing
    Skiing
More amenities
US $336/Night 7 Nights - US $2,352

Greendale Large Vacation Homes

House
Map-icon
like-icon9.6
Exceptional
(112 Reviews)
2 Bedrooms 1 Bath 11 Guests 1034 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $93/Night 7 Nights - US $651
House
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4 Bedrooms 4 Baths 12 Guests
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
US $1,000/Night 7 Nights - US $7,000
Apartment
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5 Bedrooms 2 Baths 11 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $353/Night 7 Nights - US $2,472

Discover & compare premier experiences around Greendale

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Greendale Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Greendale

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can enhance your experience, as the region offers distinct seasonal pleasures that cater to various interests and preferences.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll enjoy the region's vibrant atmosphere and pleasant weather, making it an ideal time for outdoor activities and exploring local attractions.

Average Temperature Daytime: around 85°F - Nighttime: 65°F
autumn
Fall (September to November)

This season offers cooler temperatures and colorful foliage, perfect for experiencing the area's natural beauty and enjoying outdoor recreation in a comfortable climate.

Average Temperature Daytime: about 75°F - Nighttime: 55°F

Off-Season Highlights

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Winter (December to February)

While the winter months are quieter, you can find cozy accommodations to relax and enjoy the peaceful scenery of this destination during the colder season.

Average Temperature Daytime: around 40°F - Nighttime: 25°F
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Spring (March to May)

In early spring, the area begins to bloom, providing a tranquil environment before the busy summer season, with mild temperatures perfect for exploring at your own pace.

Average Temperature Daytime: about 60°F - Nighttime: 40°F

Weekly Weather Forecast for Greendale

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for meals amidst the scenic surroundings of the area.
  • Relax on private patios or decks that offer views of the natural beauty here.
  • Make use of well-maintained gardens and landscaped yards to unwind outdoors.
  • Benefit from community pools and outdoor swimming options available at some properties.
  • Take advantage of outdoor fireplaces or fire pits for cozy evenings under the stars.
  • Explore spacious yards suitable for outdoor activities like playing or picnics.
  • Utilize nearby walking or biking trails that showcase the local landscape and scenery.
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Family Activities

  • Greendale Community Park: Enjoy a family picnic, playground fun, and scenic walking trails at this well-maintained local park.
  • Indianapolis Zoo: Spend a delightful day exploring diverse animal exhibits and engaging educational programs in nearby Indianapolis, just a short drive away.
  • Greenwood Amphitheater: Catch family-friendly outdoor concerts and events in an inviting setting that offers entertainment for all ages.
  • Trails at the Grand Kankakee Marsh: Discover nature through easy hiking and birdwatching opportunities set within the region’s preserved wetlands.
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Adult Activities

  • Greendale Historic District Tour: Immerse yourself in local history by exploring the well-preserved architecture and charming streets of this area's historic district.
  • Local Dining Experiences: Savor authentic regional cuisine at one of the neighborhood’s popular restaurants, offering a taste of the area's culinary heritage.
  • Parks and Recreation: Enjoy outdoor activities like walking or picnicking at nearby parks that provide scenic views and peaceful surroundings.
  • Community Events and Markets: Engage with local culture by attending seasonal markets and community festivals celebrated throughout the region.

Other Places to Stay in Greendale, IN

Competition Racing Indoor Karting Center

Greendale Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region's charming restaurants and cafes to enjoy authentic cuisine and experience the area's vibrant food scene.
  • Plan Outdoor Activities: Make the most of your stay by engaging in outdoor pursuits such as hiking, cycling, or relaxing in nearby parks that showcase the natural beauty of this destination.
  • Discover Unique Neighborhoods: Wander through different neighborhoods to get a true sense of local culture and find hidden gems that enrich your visit.
  • Utilize Local Transportation: Use available transit options or walkable routes to easily explore the area’s attractions and maximize your time here without hassle.

Transportation Options

  • Greendale Transit Bus Service: This reliable bus service offers convenient transportation throughout the neighborhood, making it easy to explore the area without a car.
  • Local Taxi Services: Numerous taxi companies operate here, providing quick and comfortable rides for travelers seeking flexible transportation options in this part of Indiana.
  • Rideshare Options: Popular rideshare apps are widely available in the region, allowing you to easily connect with drivers for door-to-door service around your vacation rental.
  • Car Rentals at Nearby Airports: If you're arriving by air, several rental agencies at nearby airports provide cars suitable for exploring here and beyond in Indiana.

Local Customs Options

  • Community Festivals: Participating in local festivals is a cherished tradition here, offering you a chance to enjoy regional music, food, and crafts that celebrate the area's heritage.
  • Chamber of Commerce Events: Attending events organized by the local chamber provides insight into the community's spirit and helps you connect with its residents during your stay.
  • Respect for Local History: You’ll find that preserving the area's history is a key custom, often reflected in efforts to maintain historic buildings and share stories about the region’s past.
  • Environmental Awareness: The community places importance on conservation and eco-friendly practices, encouraging visitors to respect natural spaces and participate in sustainability initiatives.

Greendale Vacation Rental Frequently Asked Questions

2. Which vacation homes in Greendale are best for families?

If you are looking for a family-friendly vacation home in Greendale, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greendale:

3. How many Rentbyowner vacation rentals are available in Greendale?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 44 in the Greendale area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greendale. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the specific property you choose. It’s best to review the individual listing details or contact the owner directly to understand the terms and any applicable fees.

5. Are there any specific check-in and check-out times I should be aware of?

Check-in and check-out times are set by the property owner and can differ from one rental to another. You should confirm these details when booking and refer to your reservation confirmation for exact times.

6. Is Wi-Fi and other amenities included with my stay?

Amenities such as Wi-Fi, appliances, and other extras are listed on each property detail page. For specific questions about available amenities, contact the host before completing your reservation.

7. How do I securely book a vacation rental in the region?

Booking is completed through the secure platform, which ensures your payment and personal information are protected. Be sure to read all listing details and reach out to the owner if you have any questions before confirming your reservation.

8. What should I know about local regulations or rules when staying in a vacation rental here?

Local regulations and house rules are typically outlined in the listing or provided by the host. It’s important to review these before your stay to ensure compliance and a smooth experience in this destination.

Greendale Top Rated Vacation Rentals

Hotel
Map-icon
like-icon8.8
Fabulous
(905 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $123/Night 7 Nights - US $860
House
Map-icon
like-icon8.8
Fabulous
(3 Reviews)
1 Bedroom 1 Bath 4 Guests 550 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $116/Night 7 Nights - US $809
Hotel
Map-icon
like-icon7.2
Very Good
(669 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $79/Night 7 Nights - US $550
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Hotel
Map-icon
like-icon6.7
Good
(415 Reviews)
5 Baths 355.21 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $80/Night 7 Nights - US $557
House
Map-icon
like-icon8.6
Fabulous
(3 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
US $157/Night 7 Nights - US $1,102