
Chesapeake Vacation Rentals
- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Our top choices for Chesapeake vacation rentals

Great Studio | Pool & Hot Tub. Your Next Vacation
Great Studio | Pool & Hot Tub. Your Next Vacation
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
3-bedroom home away from home in fabulous Chesapeake, Virginia.
3-bedroom home away from home in fabulous Chesapeake, Virginia.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Comfortable & Private 2 Bedrm Cottage w/ King bed.Find vacation rentals that suit your style
Top Chesapeake Hotel Reviews

Ocean Resort
Find out more about Chesapeake
Everything you need to know about Chesapeake vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chesapeake vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $137 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Chesapeake rentals
At Expedia, we put the best Chesapeake vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Pet-Friendly Hotels in Virginia Beach
- Extended Stay Hotels in Norfolk
- Williamsburg Hotels
- Hotels near Norfolk Intl.
- Oceanfront Hotels in Norfolk
- Vacation Homes in Virginia Beach
- Virginia Beach Hotels
- Newport News Hotels
- Condo Rentals in Virginia Beach
- Portsmouth Hotels
- All-Inclusive Resorts in Virginia Beach
- Chesapeake Hotels
- Cheap Hotels in Norfolk
- Hotels near Greenbrier Mall
- Oceanfront Hotels in Norfolk - Virginia Beach
- Cheap Hotels in Chesapeake
- Hotels near Rivers Casino Portsmouth
- Hotels with Balconies in Virginia Beach
- Hotels near Virginia Beach Boardwalk
- Hampton Hotels
- Norfolk Hotels
- Resorts in Virginia Beach
- Cheap Hotels in Virginia Beach
- Oceanfront Hotels in Virginia Beach
- Flights to Norfolk - Virginia Beach
- Flights from New York (JFK) to Norfolk (ORF)
- Flights from Dallas (DFW) to Norfolk (ORF)
- Flights from Detroit (DTW) to Norfolk (ORF)
- Flights from Houston (IAH) to Norfolk (ORF)
- Flights from Jacksonville (JAX) to Norfolk (ORF)
- Flights from New York (NYC) to Norfolk (ORF)
- Flights to Newport News
- Flights to Virginia Beach
- Flights from Baltimore (BWI) to Norfolk (ORF)
- Flights from Phoenix (PHX) to Norfolk (ORF)
- Flights from Tampa (TPA) to Norfolk (ORF)
- Flights from Chesapeake
- Flights to Chesapeake
- Flights from Philadelphia (PHL) to Norfolk (ORF)
- Flights from San Diego (SAN) to Norfolk (ORF)
- Flights from Seattle (SEA) to Norfolk (ORF)
- Flights from Minneapolis (MSP) to Norfolk (ORF)
- Flights from Atlanta (ATL) to Norfolk (ORF)
- Flights from Norfolk Intl.
- Flights from Fort Lauderdale (FLL) to Norfolk (ORF)
- Flights to Norfolk
- Flights from Orlando (MCO) to Norfolk (ORF)
- Flights from Hartford (BDL) to Norfolk (ORF)
- Flights from Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
- Flights from Los Angeles (LAX) to Norfolk (ORF)
- Flights from Denver (DEN) to Norfolk (ORF)
- Flights from Columbus (CMH) to Norfolk (ORF)
- Flights from Chicago (ORD) to Norfolk (ORF)
- Flights from Charlotte (CLT) to Norfolk (ORF)
- Flights from Pittsburgh (PIT) to Norfolk (ORF)
- Flights from Nashville (BNA) to Norfolk (ORF)
- Flights from Boston (BOS) to Norfolk (ORF)
- Franklin Vacation Rentals
- Northampton County Vacation Rentals
- Bohannon Vacation Rentals
- Topping Vacation Rentals
- Jamestown Island Vacation Rentals
- Portsmouth Vacation Rentals
- Norfolk Vacation Rentals
- Surry Vacation Rentals
- Norfolk - Virginia Beach Vacation Rentals
- Franklin City County Vacation Rentals
- Suffolk Vacation Rentals
- Gloucester Vacation Rentals
- Newport News Vacation Rentals
- Cheriton Vacation Rentals
- Virginia Beach Vacation Rentals
- Smithfield Vacation Rentals
- Lanexa Vacation Rentals
- Poquoson Vacation Rentals
- Cape Charles Vacation Rentals
- Yorktown Vacation Rentals
- Diggs Vacation Rentals
- Hampton Vacation Rentals
- Virginia Beach City County Vacation Rentals
- Toano Vacation Rentals
- Mathews Vacation Rentals
- Deltaville Vacation Rentals
- Williamsburg Vacation Rentals
- Gwynn Vacation Rentals












































































