Need a flexible short-term rental in Chesapeake? Browse fully furnished stays tailored for extended holidays, digital nomad bases, or business travel. Compare verified options to secure a convenient setup for your visit.
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 Short Term 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 short term rentals stand out?
Every short term 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 short term 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 Short-term Rentals in Chesapeake
You can explore 99 verified short-term rentals in Chesapeake, including apartments, houses, and furnished stays suitable for both travel and temporary living.
Short-term rental prices in Chesapeake vary depending on location, property size, and travel dates. Rates typically start from around $45 per night, with higher prices for premium properties or peak seasons.
Many short-term rentals in Chesapeake include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.
Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chesapeake, booking earlier can help secure better options.
In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.
Short-term rentals in Chesapeake often include amenities such as Fireplace/Heating, Internet, and Laundry, providing a comfortable and convenient stay.
Short-term rentals in Chesapeake are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.