Cumberland Rentals by Owner
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House
- Air Conditioner
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Cabin
- Air Conditioner
- Pet Friendly
- TV
Cabin
- Pet Friendly
- Security/Safety
- Child Friendly
Cabin
- Air Conditioner
- Parking
- Pet Friendly
Why Choose Rent By Owner for your Cumberland vacation rental?
What makes our Rentals by Owner special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 Rentals by Owner stay?
Choosing the ideal time to vacation here ensures you experience the region's natural beauty at its best, making your Rent By Owner rental in Cumberland, Wisconsin, the perfect home base for your memorable getaway.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy longer daylight hours and warmer weather, making it an ideal time for outdoor activities in this region. This peak season attracts visitors looking to experience the area's natural beauty and vibrant atmosphere.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn brings colorful foliage and a crisp climate, attracting travelers seeking scenic views and outdoor adventures. The cooler temperatures and stunning fall scenery make this period a popular time to visit here.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
In winter, the area transforms into a quiet retreat with colder weather, perfect for those looking to escape the crowds and enjoy peaceful surroundings. This off-peak season offers a serene environment for relaxation.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F
Spring (March to May)
Spring arrives with milder temperatures and blooming flora, but it remains less crowded compared to peak seasons. It’s a great time to explore the region's natural landscapes before the summer rush begins.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Cumberland
How to Book Your Cumberland vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. 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
Common Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner 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 dining with a private picnic area or barbecue grill to savor meals al fresco.
- Take advantage of spacious yards or gardens perfect for outdoor activities and relaxation.
- Make the most of scenic views with access to nearby lakes, forests, or other natural landscapes.
- Utilize private decks, patios, or porches ideal for unwinding while taking in the fresh air and views of the region.
- Benefit from community amenities such as shared outdoor pools or tennis courts often available in the area.
- Explore nearby hiking or biking trails directly accessible from your vacation rental’s outdoor space.
- Relax around a cozy outdoor fire pit for evenings under the stars, a popular feature in this peaceful destination.
Top Attractions Around Cumberland
What attractions are nearby?
Enjoy nearby outdoor activities such as hiking, fishing, and boating in the scenic surroundings of this destination, providing effortless access to the region’s natural beauty for an unforgettable stay.
Family Activities
- Lake Name: Spend a day boating, swimming, or fishing in this scenic lake that offers fun for the whole family.
- Cumberland Cheese Factory Tour: Discover how local cheese is made with a guided tour that’s both educational and delicious for children and adults alike.
- Pine Lake Trail: Embark on an easy hike along this trail, perfect for families to explore nature and enjoy stunning views around here.
- Cumberland Community Park: Relax and play at this inviting park equipped with playgrounds, picnic areas, and open spaces suitable for all ages.
Adult Activities
- Explore the Biking Trails: Discover scenic routes around the region that provide a great way to enjoy the outdoors and see the area's natural beauty.
- Visit Local Breweries and Wineries: Experience the craft beverages of the area by touring local breweries and wineries, perfect for an adult tasting adventure.
- Enjoy Guided Fishing Tours: Relax on a guided fishing excursion on nearby lakes, where you can unwind and try your luck in this serene setting.
- Discover Historical Landmarks: Immerse yourself in the region’s history by visiting notable landmarks and learning about the area's heritage during your stay.
Other Places to Stay in Cumberland, WI
Cumberland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the area's natural beauty by engaging in outdoor pursuits such as fishing, hiking, or boating to fully immerse yourself in the region's scenic environment.
- Choose a Rental Near Key Attractions: Select a vacation rental by owner close to popular spots to maximize your leisure time and enjoy convenient access to the area's highlights.
- Plan Seasonal Events and Festivals: Check the local calendar for seasonal festivals or events that highlight the region’s culture and traditions, enriching your stay with authentic experiences.
- Utilize Local Tips for Dining and Shopping: Seek recommendations from your host or locals to discover hidden gem eateries and shops, offering you a more genuine taste of the community here.
Transportation Options
- Local Bus Services: Convenient public transportation options are available, allowing you to easily explore the area without a car.
- Rental Car Agencies: Major rental car companies operate nearby, offering flexibility and independence for your travel plans.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps provide quick and reliable transportation throughout this region, ideal for short trips or spontaneous outings.
- Private Shuttle Services: Customized shuttle services can be arranged for specific destinations within Cumberland, ensuring a comfortable and direct journey here.
Local Customs Options
- Lumberjack Traditions: In this area, you’ll find a deep-rooted history of logging and lumberjack culture that influences local festivals and community events.
- Harvest Celebrations: Participating in seasonal harvest festivals offers a glimpse into the region’s agricultural heritage and communal spirit.
- Dockside Customs: The community values its lakeside lifestyle with customs centered around boating, fishing, and water safety prevalent throughout here.
- Local Artisanship: Supporting regional artisans and craft traditions is common, reflecting the area's appreciation for handmade goods and local craftsmanship.
Frequently Asked Questions About Cumberland Rentals by Owner
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:
- QUIET LAKE HOME RURAL SETTING
- Farmhouse Retreat
- Relax on the lake!
- Poskin Lake Getaway Cabin Lakefront access and beautiful sunrise
- Modern Lake Home with Pickleball and Pontoon available to rent.
- Sundown on North Pipe
- Cabin Retreat - 90 minutes from Twin Cities - Can accommodate up to 10 people
- Rustic Home by the Lake
- Kodiak - Hot Tub/Sauna
- The Lake Home on Beaver Dam Lake in Cumberland, Wisconsin
2. How many Rentbyowner vacation rentals are available in Cumberland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 70 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.
3. What is the cancellation policy for a rental by owner in Cumberland, Wisconsin?
The cancellation policy varies depending on the individual listing. To ensure you understand the specific terms, please review the cancellation details provided in each rental listing or contact the owner directly before booking.
4. Are there any additional fees when booking a rental by owner in the area?
Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing details. We recommend reading through these details carefully or reaching out to the owner to clarify any potential extra costs.
5. How do I confirm my booking for a property listed by an owner in Cumberland?
Your booking is confirmed once you complete the reservation process and receive confirmation from the owner or the platform. Be sure to follow all steps indicated in the listing and communicate with the owner if you have any questions.
6. What amenities can I expect when staying at a rental by owner in the region?
Amenities vary between properties. Each listing provides detailed descriptions of what is included, such as Wi-Fi, kitchen facilities, or outdoor spaces. Review the listing carefully to ensure it meets your needs before booking.
7. Are pets allowed at rental homes in Cumberland, Wisconsin?
Pet policies differ among owners. Some rentals may allow pets, while others do not. Check the specific listing details or contact the owner directly to confirm whether pets are permitted during your stay.
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