Discover Your Perfect Chesapeake Vacation Homes

Best Vacation Homes in Chesapeake

See More Chesapeake Vacation Rentals

Chesapeake Luxury Rentals

See More Chesapeake Luxury Vacation Rentals
Find More Chesapeake Villas, Resorts, & Rentals on BedroomVillas

Chesapeake Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Chesapeake on PetFriendly.io

Why Choose Rent By Owner for your Chesapeake Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Chesapeake Vacation Rentals

Where are the best neighborhoods to stay in Chesapeake?

When selecting a neighborhood to stay in Chesapeake, Virginia, you'll find a variety of charming districts that cater to different preferences. Each area offers unique local flair and convenient access to the city’s attractions and amenities. Whether you're seeking a quiet residential community or a lively locale close to natural parks, Chesapeake’s neighborhoods provide excellent options for booking your vacation rentals. This diversity ensures you can find the perfect setting to enjoy your time in this welcoming city, making your experience both comfortable and memorable.

Greenbrier East

In Greenbrier East, you can enjoy a tranquil setting with convenient access to local amenities, making it an ideal choice for those seeking comfort and accessibility in Chesapeake. This neighborhood provides a peaceful retreat while being close to key attractions within the region.

View 38+ Rentals in Greenbrier East

Churchland

Located just outside the core of the area, Churchland offers a friendly community atmosphere with easy connectivity to nearby city conveniences. It’s perfect for travelers wanting a blend of suburban charm and proximity to regional highlights.

View 73+ Rentals in Churchland

Greenbrier West

Greenbrier West presents a welcoming environment with spacious surroundings, ideal for visitors looking to explore Chesapeake from a comfortable base. Its location makes it simple to reach popular destinations throughout the region.

View 82+ Rentals in Greenbrier West

Great Bridge

Known for its historic significance, Great Bridge is a charming neighborhood that combines cultural interest with modern conveniences. It’s a fantastic spot for exploring local history while enjoying the comforts of a well-connected area.

View 137+ Rentals in Great Bridge

Western Branch North

Western Branch North features a peaceful residential setting with easy access to outdoor activities and regional highways, making it suitable for travelers looking for a quiet retreat with convenient travel options within Chesapeake.

View 26+ Rentals in Western Branch North

Deep Creek South

Deep Creek South offers a relaxed atmosphere with local parks and open spaces, ideal for visitors interested in enjoying the natural beauty of the area while staying close to Chesapeake’s main attractions.

View 165+ Rentals in Deep Creek South

Great Bridge East

This part of Chesapeake provides easy access to both historical sites and modern amenities, making it a practical choice for travelers who want to explore the region thoroughly from a comfortably situated neighborhood.

View 535+ Rentals in Great Bridge East

Best Times to Visit Chesapeake

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit for your stay ensures you experience the region's best features, whether you prefer a lively summer atmosphere or a quieter off-season in Chesapeake, Virginia.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the weather tends to be warm and pleasant, making it ideal for exploring the area's outdoor attractions and enjoying your stay.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Early Fall (September to October)

This season offers mild temperatures and less crowded conditions, providing a comfortable environment to relax and discover the region's local charm.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 60°F

Off-Season Highlights

image
Winter (December to February)

The cooler months bring lower tourist traffic, allowing you to experience the area's tranquility and affordability with cozy accommodations.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
image
Late Spring (April)

Before the peak summer rush begins, April offers mild weather and fewer visitors, perfect for enjoying the peaceful ambiance of your vacation rental and nearby surroundings.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 50°F

Weekly Weather Forecast for Chesapeake

How to Book Your Chesapeake 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 Chesapeake

More Top-Rated Vacation Rentals in Chesapeake 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 your outdoor space with a private patio or deck, perfect for relaxing in the fresh air.
  • Take advantage of a spacious backyard area suitable for family gatherings or outdoor activities.
  • Experience the region's pleasant climate with access to a well-maintained garden or landscaped grounds.
  • Make the most of outdoor dining opportunities with a barbecue or grill setup available at many properties.
  • Stay active with outdoor amenities like a swimming pool or a sports court included in some vacation rentals.
  • Explore the area's natural beauty through nearby walking trails or nature paths often accessible from the property.
  • Relax by a cozy fire pit during cooler evenings, ideal for socializing and enjoying the region’s peaceful scenery.

Top Attractions Around Chesapeake

What attractions are nearby?

In this vibrant destination, you can enjoy a variety of outdoor activities and explore local parks, museums, and recreational spots that highlight the best of what the region has to offer, making your stay memorable and enjoyable.

image
image

Family Activities

  • Chesapeake Bay Maritime Center: Explore interactive exhibits and hands-on activities that educate your family about the region's maritime history and its significance to this coastal destination.
  • Great Dismal Swamp National Wildlife Refuge: Embark on scenic nature trails and observe local wildlife in a peaceful setting that offers educational opportunities for children and adults alike.
  • Hickory Ridge Farm and Market: Enjoy a family-friendly farm experience with seasonal activities, animal encounters, and fresh local produce within the area’s vibrant rural surroundings.
  • Greenbrier Mall and Park: Spend quality time at this shopping and recreational hub featuring outdoor play areas, walking trails, and entertainment options suitable for all ages.
image

Adult Activities

  • Visit the Chesapeake Arboretum: Explore this peaceful natural space to enjoy scenic walking trails and discover native Virginia flora, perfect for a relaxing outdoor activity.
  • Discover the Chesapeake Maritime Center: Learn about the region's rich maritime history through engaging exhibits and interactive displays that highlight local naval and commercial shipping heritage.
  • Enjoy a round of golf at Elizabethan Downs Golf Course: Tee off at this well-maintained course offering a challenging and enjoyable experience amidst the area's scenic landscape.
  • Explore the City Park: Take advantage of this urban park’s amenities, including playgrounds, walking paths, and picnic areas, ideal for unwinding after a day of exploring here.

Other Places to Stay in Chesapeake, VA

Great Bridge East
Great Bridge East Vacation Rentals
Cahoon Plantation Golf Course
Cahoon Plantation Golf Course Vacation Rentals
Deep Creek South
Deep Creek South Vacation Rentals
Chesapeake City County
Chesapeake City County Vacation Rentals
Portlock Galleries at SoNo
Portlock Galleries at SoNo Vacation Rentals
Chesapeake Veterans' Memorial
Chesapeake Veterans' Memorial Vacation Rentals
Great Bridge
Great Bridge Vacation Rentals
Greenbrier West
Greenbrier West Vacation Rentals
South Norfolk
South Norfolk Vacation Rentals
Jolliff
Jolliff Vacation Rentals
Greenbrier East
Greenbrier East Vacation Rentals
Western Branch North
Western Branch North Vacation Rentals
More Places to Stay Near Chesapeake

Chesapeake Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Make the most of your stay by visiting popular landmarks and sites that showcase the unique charm of Chesapeake, Virginia.
  • Engage with the Community: Take time to participate in local events or visit community spots to truly experience the area's vibrant culture.
  • Plan Outdoor Activities: Utilize the region’s parks and natural spaces for outdoor adventures like walking, biking, or relaxing amidst scenic views.
  • Choose Well-Located Vacation Rentals: Book accommodations close to key attractions and amenities to maximize convenience and reduce travel time during your visit.

Transportation Options

  • Chesapeake Bus System (The Tide): Offers convenient local transit options to explore the area with ease, making it simple to navigate this region without a car.
  • Amtrak Rail Service: Connects here to major cities along the East Coast, providing a reliable rail option for travel within the region and beyond.
  • Norfolk International Airport: Serves as the primary airport nearby, offering domestic flights that help you easily reach this destination from across the country.
  • Taxi and Rideshare Services: Available throughout the area, these provide flexible and on-demand transportation for getting around while staying in Chesapeake.

Local Customs Options

  • Southern Hospitality: You will notice the warm and welcoming attitude that characterizes social interactions in this area, reflecting its deep-rooted Southern traditions.
  • Barbecue Etiquette: Enjoy experiencing local barbecue customs, which emphasize communal sharing and appreciation for slow-cooked, flavorful dishes typical of the region.
  • Fishing and Boating Customs: Engaging in fishing and boating is a common pastime here, with a respectful approach toward conservation and environmental awareness embraced by locals.
  • Community Festivals: Participating in seasonal festivals offers insight into traditional music, crafts, and food that celebrate the local heritage of this destination.

Frequently Asked Questions About Chesapeake?

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 vacation rentals have private pools in Chesapeake?

There are 9 vacation rentals with private pools near Chesapeake. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 166 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. 

5. What is the cancellation policy for vacation rentals in Chesapeake, Virginia?

Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms and any potential fees involved before booking.

6. How do I check for availability and secure my reservation in Chesapeake's vacation rentals?

Availability can be checked through the listing calendar on the property page. Once you find a suitable option, you can proceed with the booking process, which typically involves contacting the owner or completing an online reservation.

7. Are there any additional fees or charges when booking a vacation rental here?

Additional fees such as cleaning charges, service fees, or taxes are often included in the listing details. It’s best to review the breakdown provided during your booking process or reach out to the owner for clarification.

8. What amenities are usually available in vacation rentals in this area?

Most properties often feature essential amenities like Wi-Fi, parking, and kitchen facilities. To find specific amenities, review the property's description and photos or contact the owner before confirming your stay.

9. How close are the vacation rentals to local attractions and transportation options?

Many rentals are conveniently located to provide easy access to key attractions and transportation. For precise location details and proximity to transit, refer to the property listing or contact the owner for more information.

Chesapeake Top Rated Vacation Rentals

See More Chesapeake Vacation Rentals