Looking for the ideal vacation rental in Chesapeake? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.
Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family
AC, Dryer, Internet, Laundry, No Smoking, Washer
Exceptional
2 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
Exceptional
1 reviews
AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
21 reviews
Balcony/Terrace, Parking, Internet, Air Conditioner, Child Friendly
AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry
Air Conditioner, Security/Safety, View, Kitchen, Fireplace/Heating, Internet, Parking
Good
6 reviews
AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay
Review score
1 reviews
Free Parking, Internet, Pool, Washer And Dryer
Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay
AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
1 reviews
Apartments, Accommodations, Parking, Lodgings, Places to stay
AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking
Apartments, Accommodations, Parking, Lodgings, Places to stay
Good
2 reviews
AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer
Review score
1 reviews
Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering
Exceptional
47 reviews
AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry
Review score
2 reviews
Fabulous
4 reviews
AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area
Exceptional
4 reviews
AC, Dryer, Fireplace, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Living Area
Superb
3 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Chesapeake.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our vacation rentals stand out?
Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best vacation rentals in Chesapeake are:
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
You can explore 92 verified vacation rentals in Chesapeake. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.
Vacation rental prices in Chesapeake vary depending on the season, property size, and location. Rates typically start from around $45 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.
Most vacation rentals in Chesapeake include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.
Yes, many vacation rentals in Chesapeake welcome pets. Currently, 24 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.
For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.
Vacation rentals in Chesapeake often include amenities such as Fireplace/Heating, Internet, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.
You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.