Best Vacation Homes in Chesapeake
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
- Parking
- Balcony/Terrace
- Kitchen
- Parking
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Parking
- Internet
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Hot Tub
- Fireplace/Heating
- Kitchen
Chesapeake Luxury Rentals
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Hot Tub
- Fireplace/Heating
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Fireplace/Heating
- Kitchen
- Parking
Chesapeake Pet Friendly Vacation Rentals
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Pet Friendly
- Parking
- Fireplace/Heating
- Pool
- Pet Friendly
- Private Pool
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Chesapeake Large Vacation Homes
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Hot Tub
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
Why Choose Rent By Owner for your Chesapeake Vacation Rental Homes?
What makes our Vacation Rentals special?
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 27+ Rentals in Greenbrier EastChurchland
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 63+ Rentals in ChurchlandGreenbrier 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 60+ Rentals in Greenbrier WestGreat 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 103+ Rentals in Great BridgeWestern 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 70+ Rentals in Western Branch NorthDeep 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 145+ Rentals in Deep Creek SouthGreat 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 27+ Rentals in Great Bridge EastBest 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
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.
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.
Off-Season Highlights
Winter (December to February)
The cooler months bring lower tourist traffic, allowing you to experience the area's tranquility and affordability with cozy accommodations.
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.
Weekly Weather Forecast for Chesapeake
How to Book Your Chesapeake Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Chesapeake
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 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.
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.
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
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.
Chesapeake Vacation Rental Frequently Asked Questions
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:
- Beautiful home in Chesapeake
- Fully renovated and Modernized home in Chesapeake
- YourSpace Hotels Chesapeake
- Oasis at the Creek
- Bright Chesapeake Home Near Shopping & Dining
- Southern Charm Warm and WelcomenEntire home hosted by Annetten4 guests
- The Sparks Home! Relaxing Space + Lux Kitchen
- Beautiful home in Chesapeake
- Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub
- Great Studio | Pool & Hot Tub. Your Next Vacation
2. How many vacation rentals have private pools in Chesapeake?
There are 8 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 2026 is over 183 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?
6. How do I check for availability and secure my reservation in Chesapeake's vacation rentals?
7. Are there any additional fees or charges when booking a vacation rental here?
8. What amenities are usually available in vacation rentals in this area?
9. How close are the vacation rentals to local attractions and transportation options?
Chesapeake Top Rated Vacation Rentals
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pool
- Balcony/Terrace
- Breakfast
- Pool
- Breakfast
- Kitchen
- Private Pool
- Oceanfront
- Fireplace/Heating
