Discover Your Perfect Greenwood Vacation Homes

Best Vacation Homes in Greenwood

9.4 (12 Reviews)
Bed & Breakfast
Maon House Bed and Breakfast
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
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Greenwood Luxury Rentals

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Why Choose Rent By Owner for your Greenwood 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 Greenwood

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the region’s optimal seasons when the weather is ideal for outdoor activities and local events, ensuring a memorable experience at your chosen vacation rentals here.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, the region experiences its peak visitation, making it ideal for outdoor activities and enjoying the natural beauty of this destination.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
autumn
Fall (September to November)

This season offers stunning fall foliage that attracts visitors seeking scenic drives and outdoor adventures in the region's vibrant autumn landscapes.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F

Off-Season Highlights

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Winter (December to February)

The winter months bring colder temperatures and fewer visitors, providing a peaceful retreat for those looking to enjoy snow-covered scenery and quiet moments.

Average Temperature Daytime: 20-30°F - Nighttime: 10-20°F
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Spring (March to May)

As the area awakens from winter, spring offers a quieter experience with blooming flowers and mild weather, perfect for exploring at a leisurely pace.

Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F

Weekly Weather Forecast for Greenwood

How to Book Your Greenwood Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

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.

Explore and book the perfect rental in Greenwood

More Top-Rated Vacation Rentals in Greenwood Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 cooking with a private grill for barbecues in the fresh air.
  • Relax on a spacious patio or deck, perfect for soaking up the sun or evening gatherings.
  • Take advantage of scenic views from a private balcony or porch.
  • Make use of nearby hiking trails or biking paths to explore the natural surroundings.
  • Utilize outdoor fire pits for cozy nights under the stars.
  • Benefit from well-maintained lawns for outdoor games and activities.
  • Secure parking areas or driveways to conveniently access your rental while exploring the region.

Top Attractions Around Greenwood

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic trails just moments from your vacation rentals in Greenwood, Wisconsin.

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Family Activities

  • Greenwood Community Park: Spend quality time outdoors at the local park, where family-friendly amenities and scenic picnic spots await you in this charming area.
  • Wilson Creek Wildlife Area: Explore nature with your family through hiking and wildlife observation in this tranquil natural reserve nearby.
  • Local Fishing Spots: Enjoy a relaxing day casting lines at family-accessible fishing locations that offer fun for all ages in the region.
  • Community Events and Festivals: Participate in seasonal events and festivals held throughout the year, perfect for creating memorable family experiences here.
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Adult Activities

  • Golfing at Greenwood Golf Course: Enjoy a leisurely round of golf at the scenic Greenwood Golf Course, where picturesque views and well-maintained fairways make for a relaxing day on the links.
  • Canoeing and Kayaking on Local Lakes: Explore the tranquil waters surrounding here by canoe or kayak, offering an immersive experience in the area's natural beauty and peaceful surroundings.
  • Hiking in Nearby State Parks: Discover the region’s diverse landscapes with a hike through nearby state parks, providing scenic trails and opportunities to connect with nature.
  • Fishing Excursions on Area Waterways: Spend your day fishing on local lakes and rivers, where you can unwind while trying to catch some of the region’s abundant freshwater fish.

Other Places to Stay in Greenwood, WI

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Hillsboro Vacation Rentals
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Greenwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature: Take advantage of the area's scenic parks and outdoor spaces to enjoy activities like hiking, fishing, or simply relaxing in the natural surroundings.
  • Discover Regional Cuisine: Savor the local flavors by visiting nearby eateries that showcase regional ingredients and culinary traditions unique to this destination.
  • Plan Off-Peak Visits: Schedule your stay during less busy times to experience a more peaceful atmosphere and better access to popular spots within the region.
  • Engage with the Community: Connect with local residents and participate in community events to gain authentic insights and enrich your travel experience here.

Transportation Options

  • Greenwood County Airport: This regional airport offers convenient flights for travelers heading to the area, with options for private and commercial aviation.
  • Local Bus Services: Reliable bus transportation connects Greenwood to nearby towns and cities, making it easy to explore the region without a car.
  • Car Rentals: Numerous car rental agencies in the vicinity provide flexible transportation options to explore this destination at your own pace.
  • Taxis and Rideshare Services: Taxis and rideshare companies operate within the area, offering quick and convenient transport directly from your vacation rental.

Local Customs Options

  • Traditional Potluck Gatherings: Sharing meals during community events is a cherished custom that emphasizes hospitality and togetherness here.
  • Local Craftsmanship Celebrations: Participating in or observing these events offers a glimpse into the region’s unique artisanal heritage.
  • Seasonal Festivals: Marking seasonal changes with festivals highlights the area's rich cultural traditions and communal spirit.
  • Respect for Nature and Outdoor Activities: Engaging in outdoor pursuits like fishing and hiking reflects the region’s deep-rooted appreciation for its natural environment.

Frequently Asked Questions About Greenwood?

1. What are the top vacation rentals in Greenwood?

There are a lot of options in Greenwood. If you plan on staying in the Greenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greenwood:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 99 in the Greenwood 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 Greenwood. 

4. What is the cancellation policy for vacation rentals in Greenwood, Wisconsin?

Cancellation policies vary by property owner, so it's important to review the specific listing details or contact the host directly to understand the terms applicable to your booking in this area.

5. Are there any house rules I should be aware of before booking?

Yes, each vacation rental has its own set of house rules provided in the listing. It's recommended to read these carefully and reach out to the host if you have any questions or need clarifications.

6. What amenities are typically included in Greenwood’s vacation rentals?

Amenities can differ among properties, but common features often include Wi-Fi, parking, kitchen facilities, and outdoor spaces. To confirm what's available, please check the specific listing details or contact the property owner.

7. How do I know if the vacation rental is suitable for my needs?

You should review the property description, photos, and guest reviews on the listing. If you have particular requirements, reaching out directly to the owner can help ensure the rental meets your expectations.

8. What is the process for checking in and out of a vacation rental in this destination?

Check-in and check-out procedures vary by property. Details are generally provided in the listing or communicated by the host. It’s best to read these instructions carefully or contact the owner for guidance before your arrival.