Discover Your Perfect Cumberland Vacation Homes

Cumberland Luxury Rentals

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Cumberland Pet Friendly Vacation Rentals

10.0 (38 Reviews)
House
Sundown on North Pipe
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Cumberland 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 Cumberland

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, whether you prefer lively seasons or quieter periods in this scenic region of Wisconsin.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, this destination experiences its peak tourism season, making it ideal for outdoor activities and enjoying the scenic beauty of the area.

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

As the region's foliage reaches its vibrant peak, visitors flock here to experience the stunning autumn colors and comfortable weather conditions.

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

Off-Season Highlights

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Winter (December to February)

The colder months see fewer visitors, offering a peaceful retreat with opportunities for winter-based activities and cozy accommodations.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 10°F
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Spring (March to May)

Early spring is a quieter time before the summer rush begins, with mild weather that’s perfect for exploring the calm and natural surroundings.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Cumberland

How to Book Your Cumberland 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 Cumberland

More Top-Rated Vacation Rentals in Cumberland 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 spacious outdoor seating areas perfect for relaxing and dining while taking in the natural beauty of the region.
  • Benefit from access to private or shared fire pits, ideal for evening gatherings under the stars.
  • Take advantage of well-maintained hiking trails or nature paths directly from your rental property.
  • Make use of on-site outdoor grilling stations to cook meals amid scenic surroundings.
  • Stay active with nearby lakes or ponds that offer opportunities for kayaking, canoeing, or fishing.
  • Experience the convenience of ample parking spaces or boat slips if exploring by water is part of your plans.
  • Relish in lush lawns and gardens suitable for outdoor games or simply enjoying the peaceful ambiance of the area.

Top Attractions Around Cumberland

What attractions are nearby?

Within this scenic region, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring local parks, all just moments from your vacation rental in Cumberland, Wisconsin.

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Family Activities

  • Patricia Lake Recreation Area: Enjoy family-friendly activities such as swimming, kayaking, and picnicking at this scenic spot close to Cumberland's vacation rentals.
  • Cumberland Community Center & Park: Engage in indoor sports, arts and crafts, and various community events perfect for a fun-filled day with children.
  • Cumberland Historical Museum: Discover the area's history through engaging exhibits that provide educational entertainment for all ages within this charming town.
  • Outdoor hiking and biking trails: Explore the region’s natural beauty on well-maintained trails suitable for family outings and outdoor adventures near your vacation rental.
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Adult Activities

  • Fishing on Lake Waconia: Enjoy a relaxing day casting your line in the pristine waters, known for excellent fishing opportunities right here in the region.
  • Hiking along the Northern Lights Trail: Explore scenic trails that wind through this destination's natural beauty, offering peaceful walks and stunning views.
  • Exploring local breweries and distilleries: Experience the region’s vibrant craft beverage scene by visiting popular local spots to taste unique brews and spirits.
  • Relaxing at the area’s golf courses: Tee off at well-maintained golf courses nearby, perfect for enjoying a leisurely round amidst beautiful landscapes.

Other Places to Stay in Cumberland, WI

McKinley
McKinley Vacation Rentals
Maple Plain
Maple Plain Vacation Rentals
The Dancing Bird
The Dancing Bird Vacation Rentals
Lakeland
Lakeland Vacation Rentals
More Places to Stay Near Cumberland

Cumberland Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Explore local outdoor recreational options and book activities early to ensure a memorable experience here.
  • Choose the Right Vacation Rental: Select accommodations that offer comfortable amenities and convenient access to the area's natural attractions for a relaxing stay.
  • Discover Local Dining Options: Try out regional eateries and grocery stores nearby to enjoy authentic cuisine amidst the scenic surroundings.
  • Stay Connected and Prepared: Keep essential information handy, including maps and contact details, to navigate the region efficiently during your visit.

Transportation Options

  • Personal Vehicle: Driving your own car offers the flexibility to explore the area and access Cumberland's scenic surroundings at your own pace.
  • Local Bus Services: Scheduled bus routes connect key points within this destination, providing an affordable way to get around without the need for a car.
  • Taxis and Rideshare Services: Reliable options like taxis or rideshare apps are available here, offering convenient transportation directly from your vacation rental.
  • Rental Cars: Renting a vehicle on-site grants you the freedom to venture into nearby attractions and enjoy the region's natural beauty effortlessly.

Local Customs Options

  • Local Lake Traditions: Engaging in the region’s well-loved fishing and boating practices allows you to connect with Cumberland's lakeside community.
  • Community Festivals: Participating in seasonal celebrations, such as the annual summer fair, highlights the area's vibrant local culture and friendly spirit.
  • Wildlife Respect: Observing wildlife etiquette is important here, ensuring that nature remains pristine for future visitors and residents alike.
  • Traditional Hunting Practices: For those interested in outdoor pursuits, understanding and respecting local hunting customs enriches your experience in this area’s natural environment.

Frequently Asked Questions About Cumberland?

1. What are the top vacation rentals in Cumberland?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 76 in the Cumberland 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 Cumberland. 

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

Cancellation policies vary depending on the property listing. You should review the specific cancellation terms outlined in the rental details or contact the property owner directly to understand your options before booking.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning, service charges, or security deposits are typically specified in the listing. It’s advisable to read the full description and communicate with the owner to clarify any extra costs associated with your stay.

6. What amenities can I expect at vacation rentals in this area?

The amenities offered can differ from one property to another. Review each listing carefully to see what features are included, such as Wi-Fi, kitchen facilities, or outdoor space, ensuring they meet your needs for a comfortable stay.

7. How do I ensure my reservation in Cumberland, Wisconsin is secure?

Book through trusted platforms that offer secure payment gateways and verified listings. Always confirm the property details and communicate with the owner through official channels to maintain a safe and reliable booking process.

8. What should I do if I need to change or cancel my reservation?

You should consult the specific cancellation policy outlined in your booking confirmation or contact the property owner directly. This will help you understand your options and any potential penalties related to modifications or cancellations.