Best Vacation Homes in Cumberland County
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Parking
- Pet Friendly
- Accessibility
Cabin
- Parking
- Pet Friendly
- Balcony/Terrace
Cumberland County Luxury Rentals
Other
- Air Conditioner
- Parking
- Pool
Other
- Air Conditioner
- Parking
- TV
House
- Parking
- Pet Friendly
- Accessibility
House
- Air Conditioner
- Parking
- Pet Friendly
Cabin
- Parking
- Pet Friendly
- Balcony/Terrace
House
- Air Conditioner
- Parking
- Balcony/Terrace
House
- Air Conditioner
- Parking
- Pet Friendly
Cumberland County Pet Friendly Vacation Rentals
Why Choose Rent By Owner for your Cumberland County Vacation Rental Homes?
What makes our Vacation Rentals 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 County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can enhance your experience, as the region offers optimal conditions for outdoor activities and relaxation during specific seasons, making it ideal for booking your vacation rentals here.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the area experiences warm weather ideal for outdoor activities and exploring local scenery, making it an excellent period for booking vacation rentals that offer a comfortable base for your adventures.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Early Fall (September to October)
This season offers mild temperatures and vibrant natural surroundings, attracting visitors looking to enjoy outdoor pursuits in a pleasant climate while securing quality accommodations in advance.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
With cooler temperatures and fewer tourists, this is a peaceful time to find affordable vacation rentals and enjoy the quieter side of the region without the crowds.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Late Fall (November and early December)
As temperatures drop and the holiday season approaches, fewer visitors are present, offering you a tranquil experience and the opportunity to book cozy accommodations in advance.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Cumberland County
How to Book Your Cumberland County 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 County
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 areas with a private yard or garden to relax and unwind amidst nature.
- Take advantage of a fully equipped outdoor grilling station for delicious barbecues during your stay.
- Make the most of nearby hiking or walking trails that showcase the region’s scenic beauty.
- Benefit from access to a communal or private swimming pool, perfect for cooling off in warm weather.
- Experience outdoor recreational facilities such as tennis courts or sports fields available at many properties.
- Relax on a furnished porch, deck, or patio that provides a tranquil setting to enjoy the surroundings.
- Explore local parks and outdoor spaces for picnicking, birdwatching, or simply appreciating the area's natural landscape.
Top Attractions Around Cumberland County
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and cultural heritage of Cumberland County, Illinois, providing a memorable experience during your stay.
Family Activities
- Cumberland County Historical Society Museum: Dive into the area’s rich history and engage with interactive exhibits that are perfect for family learning experiences.
- Sunset Lake Park: Enjoy a day outdoors with picnicking, kayaking, and hiking opportunities in this scenic spot loved by locals and visitors alike.
- Cumberland County Fairgrounds: Experience family-friendly events and seasonal festivals that showcase local culture and entertainment throughout the year.
- Nature Trails in the Region: Explore the natural beauty through well-maintained trails that offer easy hikes suitable for all ages and skill levels.
Adult Activities
- Hiking and Nature Walks: Explore scenic trails that wind through the area's natural beauty, perfect for enjoying the outdoors and observing local wildlife.
- Fishing at Local Lakes: Cast your line in nearby lakes known for their peaceful settings and abundant freshwater fish, ideal for a relaxing day by the water.
- Historical Tours: Discover the region's rich history through guided tours and local museums that provide fascinating insights into its past.
- Golfing: Play a round on well-maintained courses that offer both challenge and enjoyment amid picturesque surroundings.
Other Places to Stay in Cumberland County, IL
Cumberland County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Research local attractions and outdoor recreation opportunities to make the most of your time here, ensuring you experience the best this destination has to offer.
- Select a Prime Location: Choose a vacation rental that’s centrally located to easily access popular sites and enjoy the natural beauty surrounding the area.
- Check Amenities Carefully: Opt for accommodations with the amenities you need, whether it’s a fully-equipped kitchen or outdoor space, to enhance your overall stay.
- Connect with Local Resources: Reach out to host or property managers for insider tips on hidden gems and upcoming events to enrich your visit to this region.
Transportation Options
- Car Rentals: Local car rental agencies offer convenient options for exploring the area at your own pace, making it easy to visit nearby attractions and scenery.
- Public Transit: Bus services provide an affordable and accessible way to get around the region without needing a personal vehicle.
- Taxi Services: Taxis and rideshare options like Uber and Lyft are available for quick, reliable transportation within the destination and to surrounding areas.
- Rental Bikes: Bike rentals are a great eco-friendly choice for exploring the local landscape and enjoying the scenic routes here.
Local Customs Options
- County Fair Traditions: Participating in locally celebrated county fairs gives you a glimpse into the region’s community spirit and family-friendly customs during your stay.
- Farmers' Market Practices: Visiting the area’s farmers' markets allows you to experience the fresh produce and handcrafted goods that reflect local agricultural traditions.
- Historical Preservation: Respect for historic sites and buildings is prominent here, offering insight into the area's rich past and cultural heritage.
- Community Events and Festivals: Engaging in seasonal festivals and parades showcases the friendly atmosphere and collective pride of the local residents.
Frequently Asked Questions About Cumberland County?
1. What are the top vacation rentals in Cumberland County?
There are a lot of options in Cumberland County. If you plan on staying in the Cumberland County 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 County:
- Vintage Charmer on Main Street
- Country Farmhouse with Private Fishing & Swimming Pond, Walking Trails & Gardens
- The Ca BIN
- A frame getaway on the Embarrass River in Charleston, Illinois
- Beautiful home, huge kitchen, strong Wi-Fi , lots of room, plenty of parking
- Charming A-frame cabin set in the woods overlooking deep wooded ravines.
- Townhouse in Greenup, IL
- Pets Welcome: Tranquil Retreat w/Yard in Jewett!
- Budget Host Inn Greenup
- Budget Host Inn
2. Which vacation homes in Cumberland County are best for families?
If you are looking for a family-friendly vacation home in Cumberland County, 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 County:
3. How many Rentbyowner vacation rentals are available in Cumberland County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 20 in the Cumberland County 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 County.
4. What is the cancellation policy for vacation rentals in Cumberland County, Illinois?
Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand their terms regarding refunds and cancellations.
5. How do I find pet-friendly vacation rentals in this region?
You can filter your search on the booking platform to display only pet-friendly options, and it’s recommended to confirm with the owner about any additional pet policies or fees.
6. Are there check-in and check-out times I should be aware of when staying in these accommodations?
Check-in and check-out times differ by property; please read the specific listing details or reach out to the host for precise arrival and departure instructions.
7. Is there free Wi-Fi available at vacation rentals in this area?
Many properties offer Wi-Fi as an amenity, but it’s best to verify this information in the listing description or contact the property owner to ensure it meets your needs.
8. What amenities are typically included in vacation rentals around here?
Amenities vary, but common features include fully equipped kitchens, outdoor spaces, and parking. For a complete list, review each listing carefully or inquire directly with the host.
