Discover Your Ideal Cumberland, Virginia Vacation Rentals for a Memorable Getaway
Discover Your Perfect Cumberland Vacation Homes
Best Vacation Homes in Cumberland
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Cumberland Luxury Rentals
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Cumberland Pet Friendly Vacation Rentals
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Cumberland Large Vacation Homes
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Why Choose Rent By Owner for your Cumberland Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Cumberland
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the region offers different attractions and weather conditions throughout the year that cater to a variety of preferences.
Peak Season Highlights
Spring (March to May)
During spring, you can enjoy the region's vibrant natural beauty, making it an ideal time for outdoor activities and exploring the area's scenic landscapes.
Fall (September to November)
Fall offers stunning foliage views and pleasant weather, perfect for sightseeing and experiencing the local charm here.
Off-Season Highlights
Summer (June to August)
In summer, the region tends to be hotter and more humid, which may make outdoor pursuits less comfortable but offers opportunities for water-based activities.
Winter (December to February)
Winter months bring cooler temperatures, with a quieter atmosphere that allows for a peaceful retreat away from peak tourist times.
Weekly Weather Forecast for Cumberland
How to Book Your Cumberland Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Cumberland
Common Vacation Rentals Amenities
What amenities can you expect?
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 a private outdoor grilling area perfect for family cookouts amidst the scenic surroundings.
- Relax in a spacious backyard with ample space for outdoor activities and picnics.
- Make use of a well-maintained, outdoor swimming pool to cool off during warm summer days.
- Take advantage of nearby walking or hiking trails accessible directly from your rental property.
- Unwind around a cozy fire pit in the evenings, ideal for storytelling and stargazing.
- Benefit from lush landscaped gardens that enhance the natural beauty of your stay here.
- Utilize outdoor furniture arrangements designed for enjoying the fresh air and beautiful views of the region.
Top Attractions Around Cumberland
What attractions are nearby?
In this destination, you can enjoy a variety of outdoor activities and exploring local attractions that highlight the charming character of the region around Cumberland, Virginia, USA.

Family Activities
- Cumberland County Courthouse & Civil War Museum: Discover local history and engage the family with educational exhibits at this iconic landmark in the heart of the area.
- Wolf Creek Greenway: Enjoy scenic walking and biking trails that weave through natural landscapes, perfect for outdoor family adventures in this region.
- Cumberland County Historical Society & Museum: Explore regional heritage through interactive displays and historical artifacts suitable for all ages in this community-rich destination.
- Prairie View Park: Relax and play in a lush setting featuring playgrounds, picnic areas, and open spaces that make for a fun family day in the area.
Adult Activities
- Explore the Cumberland State Forest: Discover scenic hiking trails and outdoor adventures nestled within this natural sanctuary, perfect for escaping into nature during your stay.
- Visit the Carter Mountain Orchard: Enjoy seasonal fruit picking and panoramic views of the region while indulging in local flavors at this popular orchard destination.
- Tour historic sites and landmarks: Immerse yourself in the area's rich history through guided tours and visits to well-preserved historic locations nearby.
- Attend local festivals and events: Experience the vibrant community spirit by participating in seasonal festivals that showcase regional culture and entertainment.
Other Places to Stay in Cumberland, VA
Cumberland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local History and Culture: Take time to discover the rich history and cultural heritage that make this destination unique, enriching your stay with meaningful experiences.
- Plan Outdoor Activities: Make the most of the area's natural beauty by engaging in outdoor pursuits such as hiking or picnicking at nearby parks or scenic spots.
- Choose a Strategic Location: Select vacation rentals that are conveniently situated near key attractions and amenities for easy access and maximum convenience.
- Connect with Local Cuisine: Sample authentic regional dishes at local eateries or prepare meals in your rental to enjoy a taste of the region’s culinary traditions.
Transportation Options
- Driving Your Car: The most flexible way to explore this destination is by car, offering convenient access to local attractions and scenic routes in the area.
- Rental Cars: Several rental agencies operate nearby, making it easy to find a vehicle that suits your needs for traveling throughout the region.
- Local Transit Services: Public bus services provide an affordable and reliable transportation option within the area, connecting you to key points of interest.
- Taxis and Rideshare Options: Taxis and rideshare services offer a convenient door-to-door travel solution in the region, ideal for short trips or when convenience matters most.
Local Customs Options
- Traditional Southern Hospitality: You’ll notice a warm and welcoming attitude here that reflects the region’s deep-rooted friendliness towards visitors.
- Community Gatherings and Festivals: Participating in local events is common, giving you a chance to experience genuine regional customs and connect with residents.
- Southern Cuisine Traditions: Enjoying classic dishes like barbecue and comfort food is an integral part of the area's culture, often celebrated during communal meals and festivals.
- Respect for Historical Heritage: Visitors are encouraged to appreciate the region’s history through local memorials and preserved landmarks, demonstrating the community’s pride in its past.
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:
- Cedar Ridge Lodge Near High Bridge Trail
- In the Village Of Powhatan- walking distance to owners restaurant
- Heart Of Farmville❤️
- The Cabin on the Ridge
- Charming Virginia Retreat w/Covered Porch & Yard!
- Rose Cottage at Chevy Chase Farm
- 2 bedroom cottage in d-town Farmville, walking distance to Longwood University.
- Happy Hollow Barndominium Retreat
- Charming Virginia Retreat with Covered Porch and Yard!
- Modern Downtown Farmville #2
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 55 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.
Cumberland Top Rated Vacation Rentals
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