Best Vacation Homes in Cumberland
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $471/Night
For 7 Nights AU $3,297
1550 ft²
4 Guests
2 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Parking
- Internet
AU $299/Night
For 7 Nights AU $2,090
AU $187/Night
For 7 Nights AU $1,309
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $178/Night
For 7 Nights AU $1,249
1345.49 ft²
6 Guests
3 Bedrooms
2 Bathrooms
House
- Pet Friendly
- Parking
- Security/Safety
AU $406/Night
For 7 Nights AU $2,840
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $262/Night
For 7 Nights AU $1,831
4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Air Conditioner
- Internet
AU $545/Night
For 7 Nights AU $3,814
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Bed & Breakfast
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $242/Night
For 7 Nights AU $1,696
Cumberland Luxury Rentals
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $859/Night
For 7 Nights AU $6,016
850 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $790/Night
For 7 Nights AU $5,532
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Parking
- Child Friendly
AU $754/Night
For 7 Nights AU $5,277
904.17 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Parking
- Air Conditioner
AU $646/Night
For 7 Nights AU $4,525
950 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $581/Night
For 7 Nights AU $4,065
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Kitchen
- Parking
AU $552/Night
For 7 Nights AU $3,867
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $537/Night
For 7 Nights AU $3,758
2000 ft²
11 Guests
3 Bedrooms
3 Bathrooms
Pet Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pet Friendly
AU $506/Night
For 7 Nights AU $3,545
Cumberland Pet Friendly Vacation Rentals
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
AU $416/Night
For 7 Nights AU $2,911
4 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Pet Friendly
- Parking
- Air Conditioner
AU $310/Night
For 7 Nights AU $2,168
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $283/Night
For 7 Nights AU $1,983
800 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $348/Night
For 7 Nights AU $2,436
4 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Pet Friendly
- Parking
- Air Conditioner
AU $307/Night
For 7 Nights AU $2,152
9 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $450/Night
For 7 Nights AU $3,149
2390 ft²
11 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $484/Night
For 7 Nights AU $3,389
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $189/Night
For 7 Nights AU $1,325
Cumberland Large Vacation Homes
AU $155/Night
For 7 Nights AU $1,083
Why Choose Rent By Owner for your Cumberland 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
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.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Fall offers stunning foliage views and pleasant weather, perfect for sightseeing and experiencing the local charm here.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
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.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
Winter months bring cooler temperatures, with a quieter atmosphere that allows for a peaceful retreat away from peak tourist times.
Average Temperature Daytime: 40°F to 50°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
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 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
Great Allegheny Passage
C&O Canal National Historic Park
Cumberland County
Bear Creek Lake State Park
Clinton
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:
- In the Village Of Powhatan- walking distance to owners restaurant
- Heart Of Farmville❤️
- Charming Virginia Retreat w/Covered Porch & Yard!
- Walk to Longwood Sleeps 6 Cozy Cottage Near Hampden-Sydney
- Farmville,walk to Longwood, Greenfront,High Bridge,minutes to Hampden-Sydney
- Castello Segreto -Charming 2-bedroom cabin-
- Happy Hollow Barndominium Retreat
- Historic Farmhouse in the Dillwyn countryside. Not far from Farmville.
- Modern Downtown Farmville #2
- Charming Virginia Retreat with Covered Porch and Yard!
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 2026 is over 69 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, Virginia?
Cancellation policies vary depending on the individual property listing. To ensure you understand the specific terms, please review the cancellation details provided in the listing or contact the property owner directly before booking.
5. Are there any special amenities available in vacation rentals here?
Amenities differ between properties, so it’s best to check each listing for details such as Wi-Fi, kitchen facilities, or outdoor spaces. You can contact the host if you need clarification on what’s included.
6. How do I find the best vacation rental deals in Cumberland, Virginia?
To secure the best rates, compare multiple listings, adjust your travel dates, and look for special offers or discounts that may be available during your preferred stay period. Reading reviews can also help identify quality accommodations.
7. What should I know about the check-in and check-out process in this region?
Check-in and check-out procedures are outlined in each listing. Some properties offer flexible times, while others have specific windows. Contact the property owner if you need additional guidance on arrival or departure arrangements.
8. Is there a minimum stay requirement for vacation rentals in Cumberland, Virginia?
Minimum stay requirements can vary between properties. Details are typically specified in the listing, or you may inquire with the host directly to confirm the duration of stay needed.
Cumberland Top Rated Vacation Rentals
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
AU $152/Night
For 7 Nights AU $1,063
356.04 ft²
10 Bathrooms
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $201/Night
For 7 Nights AU $1,409
AU $173/Night
For 7 Nights AU $1,212
AU $159/Night
For 7 Nights AU $1,112
