Discover Your Perfect Chesapeake Rentals by Owner

Chesapeake Rentals by Owner

More Top-Rated Rentals by Owner in Chesapeake Area

Why Choose Rent By Owner for your Chesapeake vacation rental?

What makes our Rentals by Owner 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 Chesapeake Rentals by Owner

Where are the best neighborhoods to stay in Chesapeake?

When choosing a neighborhood to stay in Chesapeake, Virginia, you'll find that each area offers its own unique charm and convenience. Whether you prefer the vibrant atmosphere of a lively community or a quieter residential setting, Chesapeake provides a variety of options to suit your travel needs. Staying in a neighborhood close to key amenities ensures easy access to local attractions and activities, making your visit more enjoyable and stress-free. As you explore rental options through Rent By Owner, consider locations that match your lifestyle preferences and desired experience in Chesapeake, Virginia.

Greenbrier East

In Greenbrier East, you will find a welcoming community that offers convenient access to local amenities and outdoor spaces, making it an ideal choice for those seeking comfort and practicality during their stay.

View 48+ Rentals in Greenbrier East

Churchland

Situated near the region's commercial hubs, Churchland provides a balanced blend of residential tranquility and accessibility to nearby attractions, perfect for travelers looking for a peaceful yet connected stay.

View 73+ Rentals in Churchland

Greenbrier West

Greenbrier West is known for its family-friendly atmosphere and proximity to shopping centers, offering a comfortable environment for visitors who want convenience combined with a sense of community.

View 82+ Rentals in Greenbrier West

Great Bridge

This neighborhood features a mix of historic charm and modern amenities, making it a suitable location for those interested in exploring the area's rich heritage while staying close to key facilities.

View 137+ Rentals in Great Bridge

Western Branch North

Western Branch North boasts spacious neighborhoods and easy access to outdoor recreation, providing a relaxing setting for travelers seeking both leisure and convenience.

View 36+ Rentals in Western Branch North

Deep Creek South

Here, you can enjoy a quiet, suburban environment with close proximity to parks and local services, ideal for visitors wanting a peaceful base within the region.

View 165+ Rentals in Deep Creek South

Great Bridge East

Great Bridge East offers a serene neighborhood known for its friendly atmosphere and access to natural areas, making it a great spot for those desiring a calm and accessible stay.

View 535+ Rentals in Great Bridge East

Best Times to Visit Chesapeake

When should you plan your Rentals by Owner stay?

Choosing the right time to visit here can significantly enhance your experience, allowing you to enjoy the region’s unique climate and activities at their best when booking your rental by owner through Rent By Owner in Chesapeake, Virginia, USA.

Peak Season Highlights

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Late Spring to Early Summer (May - June)

During these months, you can enjoy warm weather and longer daylight hours, making it an ideal time to explore the area’s outdoor activities and attractions.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September - October)

This period offers pleasant temperatures and fewer crowds, providing a comfortable setting for outdoor exploration and enjoying the local scenery.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December - February)

The winter months bring cooler temperatures, making it a quieter time for those seeking a peaceful retreat while avoiding peak tourist activity.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
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Late Fall (November and early December)

As the region transitions into winter, this is a less busy period, perfect for visitors looking to relax in a calm environment with fewer crowds.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Chesapeake

How to Book Your Chesapeake 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 Chesapeake

More Top-Rated Rentals by Owner in Chesapeake Area

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 living with a private backyard, perfect for relaxing or entertaining guests.
  • Take advantage of a spacious patio or deck to dine al fresco while soaking up the region's pleasant climate.
  • Make use of an outdoor grill to prepare delicious meals during your stay in this inviting destination.
  • Benefit from access to scenic gardens or landscaped yards that enhance your outdoor experience.
  • Relax by a private swimming pool or hot tub, ideal for unwinding after exploring the area.
  • Engage in outdoor activities such as badminton, volleyball, or other lawn games suitable for all ages.
  • Utilize ample parking spaces or driveways for convenient access when exploring the region’s attractions.

Top Attractions Around Chesapeake

What attractions are nearby?

Within this vibrant region, you can enjoy outdoor activities such as boating, fishing, and exploring scenic parks, making it an ideal destination for those seeking both relaxation and adventure during your stay.

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Family Activities

  • Chesapeake Arboretum: Explore the region’s lush greenery and engaging nature trails, perfect for family walks and outdoor education.
  • Oak Grove Lake Park: Spend a day enjoying scenic picnics, boat rentals, and playground activities in this outdoor sanctuary.
  • Hickory Ridge Farm: Experience farm life firsthand with fun activities like pony rides and seasonal festivals designed for families.
  • The Children's Museum of Virginia at Chesapeake: Discover interactive exhibits and hands-on activities that inspire learning and creativity for young visitors.
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Adult Activities

  • Golf Courses in Chesapeake: Enjoy a leisurely day on beautifully maintained greens at some of the area's top golf courses, perfect for testing your skills amidst scenic surroundings.
  • Shopping and Dining Experiences: Explore a variety of local shops and eateries where you can indulge in regional cuisine and find unique souvenirs in this vibrant part of Virginia.
  • Boating and Water Sports: Take advantage of accessible waterways for boating, kayaking, or paddleboarding to experience the region's aquatic beauty firsthand.
  • Nature Trails and Parks: Discover walking and biking trails through lush parks and nature reserves that showcase the natural charm of the area.

Other Places to Stay in Chesapeake, VA

Great Bridge East
Explore 535 Properties
Chesapeake City County
Explore 209 Properties
Cahoon Plantation Golf Course
Explore 170 Properties
Deep Creek South
Explore 165 Properties
Portlock Galleries at SoNo
Explore 154 Properties
Chesapeake Veterans' Memorial
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Great Bridge
Explore 137 Properties
South Norfolk
Explore 102 Properties
Greenbrier West
Explore 82 Properties
Greenbrier East
Explore 48 Properties
Jolliff
Explore 45 Properties
Western Branch North
Explore 36 Properties
More Places to Stay Near Chesapeake

Chesapeake Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the region's diverse dining options to enjoy authentic Chesapeake flavors during your stay.
  • Utilize Nature and Recreation Areas: Make the most of outdoor activities available nearby, from parks to waterfronts, to experience the area's natural beauty.
  • Plan Your Sightseeing Ahead: Research the top attractions and events to optimize your schedule and fully immerse yourself in what this destination offers.
  • Choose a Well-Located Rental: Select a rental by owner close to key sites and amenities to enhance convenience and reduce travel time throughout your visit.

Transportation Options

  • Chesapeake Transit Bus System: This reliable bus service connects various neighborhoods and key points of interest, making it easy for you to explore the area without a car.
  • Rental Cars: Numerous rental car agencies operate in the region, providing flexible mobility options whether you're visiting for leisure or business.
  • Taxi Services: Local taxi providers are available throughout here, offering convenient transportation for short trips or airport transfers.
  • Ride-Sharing Apps: Popular ride-sharing services like Uber and Lyft are widely accessible, ensuring quick and affordable travel around the region.

Local Customs Options

  • Southern Hospitality: You’ll notice the warm, friendly welcomes that reflect the region’s tradition of southern hospitality and community spirit.
  • : When dining here, it’s customary to enjoy the regional seafood specialties and engage with locals about their culinary traditions.
  • Respect for Military Heritage: The area’s strong military presence means it's important to show respect for veterans and active service members in your interactions.
  • Community Festivals: Participating in local festivals offers a great way to experience the area's rich cultural customs and meet residents sharing their traditions.

Frequently Asked Questions About Chesapeake Rentals by Owner

1. What are the top vacation rentals in Chesapeake?

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

2. How many Rentbyowner vacation rentals are available in Chesapeake?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 81 in the Chesapeake 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 Chesapeake. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary by listing, so it's important to review the specific terms outlined on the rental's page or contact the owner directly for detailed information.

4. How do I ensure the rental has the amenities I need?

Amenities are listed within each property description. If you have particular requirements, verifying the details with the owner before booking can help ensure the rental meets your needs.

5. What should I know about checking in and out at a rental by owner in this region?

Check-in and check-out procedures are generally specified in the listing or provided by the owner. Contacting the host ahead of time can ensure a smooth arrival and departure process.

6. Are there any additional fees associated with my rental stay?

Additional fees such as cleaning, service charges, or taxes are typically detailed on the listing. Confirm these details with the owner during the booking process to avoid surprises.

7. How can I communicate with the owner if I have questions or issues during my stay?

Most listings include direct contact information for the owner or property manager. Using the messaging feature on the platform allows for easy communication throughout your stay.

More Rentals You May Like Near Chesapeake

More Top-Rated Rentals by Owner in Chesapeake Area