Discover Your Perfect Cherrydale Vacation Homes

Cherrydale Luxury Rentals

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10.0 (2 Reviews)
Apartment
The Million Dollar Perch
  • Air Conditioner
  • Pet Friendly
  • View
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Cherrydale Pet Friendly Vacation Rentals

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9.4 (1847 Reviews)
Apartment
The River Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.0 (19 Reviews)
Apartment
Cityscape in the heart of Ballston
  • Air Conditioner
  • Parking
  • Pet Friendly
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Cherrydale Large Vacation Homes

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Why Choose Rent By Owner for your Cherrydale 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.

Popular Areas for Cherrydale Vacation Rentals

Where are the best neighborhoods to stay in Cherrydale?

Discover the charming neighborhoods of Cherrydale in Arlington, Virginia, where you can enjoy a peaceful residential atmosphere while remaining conveniently close to vibrant city amenities. Staying in this welcoming area offers easy access to local parks, trendy cafes, and boutique shops, making it an ideal choice for those seeking a comfortable and authentic experience. Whether you're visiting for leisure or exploring nearby attractions, choosing a vacation rental in Cherrydale provides a reliable and seamless stay in one of Arlington’s most desirable neighborhoods.

Ballston

This vibrant neighborhood offers convenient access to urban amenities and a lively atmosphere, making it an ideal choice for exploring the region while enjoying comfortable vacation rentals. Its proximity to key transportation routes ensures seamless travel throughout Arlington and beyond.

View 144+ Rentals in Ballston

Donaldson Run

Known for its peaceful residential streets and scenic views, Donaldson Run provides a relaxing setting just minutes from the area's main attractions. It's perfect for travelers seeking tranquility combined with easy access to Arlington's vibrant city life.

View 875+ Rentals in Donaldson Run

Waverly Hills

Nestled in a quiet part of Arlington, Waverly Hills offers a charming environment with convenient proximity to local parks and community amenities. This neighborhood is well-suited for visitors interested in a cozy, homely stay while exploring the area.

View 904+ Rentals in Waverly Hills

Virginia Square

A hub of education and culture, Virginia Square features a variety of dining, shopping, and entertainment options within walking distance. Its central location makes it an excellent base for discovering Arlington’s dynamic urban scene.

View 144+ Rentals in Virginia Square

Maywood

Offering a mix of historic charm and modern convenience, Maywood provides a welcoming environment with easy access to public transit and local parks. It’s an appealing choice for those wanting an authentic Arlington experience.

View 1320+ Rentals in Maywood

Woodmont

Characterized by tree-lined streets and family-friendly amenities, Woodmont is ideal for travelers seeking a quiet, community-oriented area close to Arlington's main attractions. It provides a peaceful backdrop for your stay in the region.

View 1614+ Rentals in Woodmont

Best Times to Visit Cherrydale

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation in this destination ensures you enjoy its unique charm and local experiences at their best, making your stay in Arlington's charming neighborhood truly unforgettable.

Peak Season Highlights

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Spring (March to May)

During spring, the region experiences pleasant weather ideal for exploring outdoor activities near your vacation rentals in Cherrydale. The vibrant season attracts visitors seeking comfortable daytime temperatures and blooming landscapes.

Average Temperature Daytime: 60-75°F - Nighttime: 45-55°F
autumn
Fall (September to November)

Autumn offers comfortable weather with colorful foliage, making it a popular time to stay here. The region’s scenic beauty during this period enhances your experience while enjoying your vacation rentals.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Summer (June to August)

Summertime can bring higher humidity and temperatures, but it remains a lively season with plenty of opportunities for outdoor activities. Visiting during these months allows you to enjoy less crowded vacation rentals in the area.

Average Temperature Daytime: 80-90°F - Nighttime: 65-70°F
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Winter (December to February)

Winter tends to be quieter in this destination, offering a peaceful retreat with occasional cold weather. This is an excellent time to find more affordable vacation rentals and explore the region at a relaxed pace.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F

Weekly Weather Forecast for Cherrydale

How to Book Your Cherrydale 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 Cherrydale

More Top-Rated Vacation Rentals in Cherrydale 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 a private outdoor patio or deck perfect for relaxing after exploring the area.
  • Take advantage of a spacious backyard ideal for outdoor activities or family gatherings.
  • Look for a well-maintained garden area that adds to the charm of your stay in this destination.
  • Make use of outdoor seating areas designed for al fresco dining or morning coffee.
  • Check if there is a barbecue grill available for outdoor cooking during your visit.
  • Discover nearby parks or green spaces accessible from your rental for outdoor recreation.
  • Benefit from outdoor lighting features that enhance security and ambiance during evening hours.

Top Attractions Around Cherrydale

What attractions are nearby?

In this vibrant area, you can enjoy a variety of outdoor activities, cultural experiences, and local dining options that showcase the best of Arlington and its surrounding region.

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Family Activities

  • Cherrydale Park: You can enjoy outdoor adventures and family picnics at this scenic park, offering a perfect setting for relaxation in the area.
  • Virginia Highlands Park: This local park provides playgrounds and open spaces where your family can unwind and play together amidst nature.
  • Clare & Don's Beach Shack: Savor family-friendly dining experiences with casual meals just moments from your vacation rental here in Arlington’s charming neighborhood.
  • Local Nature Trails: Explore nearby walking or biking trails that provide a fun and active way to discover the region’s natural beauty with your loved ones.
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Adult Activities

  • Visit the Arlington Historical Museum: Discover fascinating exhibits and learn about the rich history of the region during your stay.
  • Explore local parks and outdoor spaces: Enjoy peaceful walks and scenic views at nearby parks that cater to outdoor enthusiasts seeking relaxation in this area.
  • Experience craft brewing tours: Immerse yourself in the vibrant craft beer scene with brewery visits that showcase the area's innovative brewing culture.
  • Attend cultural events and festivals: Engage with the community by participating in seasonal festivals and arts events held throughout the destination.

Cherrydale Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the area's charming eateries to enjoy authentic regional cuisine during your stay.
  • Utilize nearby public transportation: Maximize your visit by using convenient transit options that connect you to Arlington's key attractions and Washington, D.C.
  • Plan outdoor activities: Engage in outdoor pursuits like walking or biking in nearby parks to experience the region's scenic beauty firsthand.
  • Book with trusted vacation rentals: Secure your ideal accommodation through reliable options that offer comfort and convenience in this desirable destination.

Transportation Options

  • Metrobus: This extensive bus system offers convenient and affordable transit options within the area and to neighboring regions.
  • Virginia Railway Express (VRE): Commuter trains provide a reliable way to travel between the region and Washington, D.C., making day trips effortless.
  • Washington Metro: The nearby Metro rail connects you directly to the city center and beyond, ideal for exploring the region without hassle.
  • Car Rentals: Renting a car is a flexible transportation choice that allows you to explore Cherrydale and its surroundings at your own pace.

Local Customs Options

  • Respect for Local History: In this area, appreciating and honoring the historic landmarks and traditions is a valued custom that visitors are encouraged to observe.
  • Community Engagement: Engaging with neighbors through local events or neighborhood gatherings fosters a welcoming atmosphere in this destination.
  • Environmental Consciousness: Practicing environmentally friendly habits, such as recycling and conserving energy, aligns with the region’s commitment to sustainability.
  • Dining Etiquette: When enjoying meals at local eateries, embracing the regional dining customs enhances your experience here.

Frequently Asked Questions About Cherrydale?

1. What are the top vacation rentals in Cherrydale?

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

2. How many vacation rentals have private pools in Cherrydale?

There are 18 vacation rentals with private pools near Cherrydale. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cherrydale are best for families?

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

4. How many Rentbyowner vacation rentals are available in Cherrydale?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1077 in the Cherrydale 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 Cherrydale. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the specific property and owner. It’s recommended to review the cancellation terms listed on the individual rental page or contact the host directly for detailed information.

6. How do I ensure my reservation in Arlington, Virginia, is confirmed?

To confirm your booking, complete the reservation process through the listing platform and verify any confirmation emails received from the host or property manager. Contact the host if you have questions about your reservation status.

7. Are there any special requirements or house rules I should be aware of?

Each property may have its own set of house rules and requirements, which are detailed in the listing description. Be sure to read these carefully before completing your booking or reach out to the host for clarification.

8. What amenities are typically included in rentals here?

Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. For specific amenities, check the listing details or contact the owner to ensure the property meets your needs.

9. How close are the vacation rentals to popular attractions or transportation options?

Most rentals in this region are conveniently located near public transportation and key attractions. For exact distances and accessibility, refer to the property’s location details on the listing or ask the host for guidance.