Discover Your Perfect Sherwood Vacation Homes

Sherwood Luxury Rentals

New
House
Simon
  • Air Conditioner
  • Parking
  • Security/Safety
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Sherwood Pet Friendly Vacation Rentals

10.0 (1 Review)
Condo
Historical Haven Steps to Downtown
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
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Why Choose Rent By Owner for your Sherwood 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 Sherwood

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, so consider the seasonal trends and weather patterns to ensure your stay in this destination aligns with your ideal vacation plans.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, this destination experiences warm and inviting weather, making it ideal for outdoor activities and enjoying the natural surroundings.

Average Temperature Daytime: around 80°F to 85°F - Nighttime: approximately 60°F to 65°F
autumn
Fall (September to November)

Autumn brings vibrant foliage and pleasant temperatures, attracting visitors seeking scenic views and outdoor exploration in the area.

Average Temperature Daytime: about 70°F to 75°F - Nighttime: roughly 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

The cold winter months offer a quieter retreat with brisk air and snow-covered landscapes, ideal for those seeking solitude and peaceful scenery.

Average Temperature Daytime: around 30°F to 35°F - Nighttime: close to 15°F to 20°F
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Spring (March to May)

Springtime showcases blossoming flora and gradually warming weather, providing a gentle transition into the lively summer season.

Average Temperature Daytime: approximately 50°F to 60°F - Nighttime: about 35°F to 45°F

Weekly Weather Forecast for Sherwood

How to Book Your Sherwood 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 Sherwood

More Top-Rated Vacation Rentals in Sherwood 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 grilling with access to a private barbecue area, perfect for family gatherings or relaxing weekend cookouts.
  • Take advantage of spacious yards ideal for outdoor games and activities amid the scenic surroundings of the region.
  • Relax on a screened porch or patio that offers a comfortable outdoor living space, allowing you to soak in the fresh air.
  • Access nearby trails and pathways for walking, jogging, or mountain biking through the natural beauty of the area.
  • Make use of a fire pit or outdoor fireplace, perfect for cozy evenings under the stars.
  • Capitalize on outdoor recreational amenities like a swimming pool or hot tub for ultimate relaxation during your stay.
  • Discover picturesque views from outdoor decks or balconies that showcase the best of the regional landscape.

Top Attractions Around Sherwood

What attractions are nearby?

In this charming area, you can explore scenic hiking trails, enjoy local parks, and experience outdoor activities that showcase the natural beauty of the region surrounding Sherwood, Wisconsin.

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Family Activities

  • Sherwood Nature Center: Explore this local nature center to enjoy guided hikes, wildlife observation, and educational programs suitable for all ages.
  • Local Farm Visits: Visit nearby farms to experience hands-on activities such as berry picking, animal petting, and learning about regional agriculture.
  • Community Parks and Playgrounds: Spend quality time at family-friendly parks featuring playgrounds, picnic areas, and open spaces for outdoor games in the area.
  • Family-Friendly Fishing Spots: Relax at accessible fishing locations where families can try their luck and enjoy the peaceful surroundings here.
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Adult Activities

  • Golfing at the Sherwood Golf Course: Enjoy a relaxing day on the greens at this well-maintained course nestled in the region, perfect for both beginners and seasoned players.
  • Exploring local wineries: Discover the area's scenic vineyards with tastings that highlight the region’s renowned winemaking craftsmanship.
  • Hiking in nearby nature reserves: Experience tranquil trails through lush landscapes, offering an ideal setting for outdoor enthusiasts seeking to connect with nature.
  • Dining at local eateries: Savor regional flavors at the area's charming restaurants, where farm-to-table ingredients reflect the region’s culinary heritage.

Other Places to Stay in Sherwood, WI

Harrison Military Trail
Harrison Military Trail Vacation Rentals
More Places to Stay Near Sherwood

Sherwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and shopping options: Take advantage of the charming eateries and shops nearby to immerse yourself in the region's authentic atmosphere.
  • Plan outdoor activities early: Whether it's exploring parks or enjoying water-based pursuits, planning ahead ensures you make the most of the area's natural beauty.
  • Utilize nearby transportation services: Opt for convenient transportation options to easily access key attractions within the destination without hassle.
  • Communicate with your hosts: Use your vacation rental hosts as a resource for insider tips and personalized recommendations in this welcoming area.

Transportation Options

  • Personal Vehicle: Having your own car offers the most flexibility for exploring the local area and visiting nearby attractions from your vacation rental in Sherwood.
  • Public Transit: Bus services provide an affordable and convenient way to navigate here, connecting you to key destinations within the region.
  • Taxi and Rideshare: Taxis and rideshare services like Uber or Lyft are readily available, offering quick transportation options for trips around the area.
  • Rental Cars: Renting a car allows you to enjoy the scenic drives and ease of access to popular spots without relying on public transport schedules here.

Local Customs Options

  • Local Harvest Celebrations: Participating in the region's seasonal harvest festivals is a common tradition, celebrating Wisconsin's rich agricultural heritage.
  • Community Potlucks: Sharing homemade dishes at community events exemplifies the friendly and communal spirit that visitors often experience here.
  • Traditional Folk Music: Enjoying local live performances featuring folk tunes highlights the area's appreciation for its musical roots.
  • Farmers' Market Etiquette: Visiting weekly farmers' markets offers a glimpse into the area's farm-to-table customs, emphasizing fresh, local produce.

Frequently Asked Questions About Sherwood?

1. What are the top vacation rentals in Sherwood?

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

2. How many vacation rentals have private pools in Sherwood?

There are 27 vacation rentals with private pools near Sherwood. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Sherwood are best for families?

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

4. How many Rentbyowner vacation rentals are available in Sherwood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 587 in the Sherwood 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 Sherwood. 

5. What is the cancellation policy for vacation rentals near Sherwood, Wisconsin?

Cancellation policies vary depending on the specific listing. You should review the cancellation terms listed on each property detail page or contact the property owner directly to understand all conditions before booking.

6. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or security deposits are typically detailed in the listing. Be sure to check the total cost breakdown and contact the owner if you have any questions.

7. How do I confirm the availability of vacation rentals here during my travel dates?

Availability can be checked instantly on each listing's calendar. If you find a suitable property, proceed with the booking or reach out to the owner for confirmation on your preferred dates.

8. What amenities are usually included in vacation rentals in this region?

Properties often include amenities like Wi-Fi, parking, kitchen facilities, and outdoor spaces. To see what’s included, review the specific listing details or contact the owner for further information.

9. What is the process for checking in and out of vacation rentals here?

Check-in and check-out procedures are outlined in each listing; many properties offer self-check-in options with key codes or lockboxes. For detailed instructions, consult the property details or communicate directly with the owner.