- Connect with Facebook
- Sign in
- Register Now!
Chesapeake Vacation Rentals - Chesapeake Rental Homes and Condos
Chesapeake
- Chesapeake Tourism
- Chesapeake Hotels
- Vacation Rentals
- Flights to Chesapeake
- Chesapeake Deals
- More On Chesapeake
- Restaurants
- Things to Do
- Travel Forum
- Travel Guide
- Photos
- Map
- Chesapeake Deals
- Discount Hotels
- Hotel & Air
- All Travel Offers
Popular vacation rentals:
Explore the world! TripAdvisor has reviews and information on over 400,000 locations, including:
Vacation Rentals
- Pattaya, Thailand vacation rentals
- Cape Cod, Massachusetts vacation rentals
- Barbados vacation rentals
- Vail, Colorado vacation rentals
- Marrakech vacation rentals
- Savannah vacation rentals
- Myrtle Beach vacation rentals
- Destin, Florida vacation rentals
- Palm Springs, California vacation rentals
- North Myrtle Beach, South Carolina vacation rentals
Explore other Chesapeake resources:
Chesapeake Vacation Rentals
The safest rental experience online
Rent from verified owners and managers, and read reviews before you book.
Find out what to expect »
In partnership with:
New and Featured
Beach Break, Virginia Beach
-
Price:
€202/night
€1,012 - €1,989/week
- Bedrooms: 4, sleeps 10
- Bathrooms: 3 Contact Manager
Sunkissed, Virginia Beach
-
Price:
€188 - €260/night
€879 - €2,614/week
- Bedrooms: 5, sleeps 14
- Bathrooms: 3 Contact Manager
Sleepin' Inn, Virginia Beach
-
Price:
€2,199 - €3,263/week
- Bedrooms: 6, sleeps 17
- Bathrooms: 4
- Min stay: 7 Contact Manager
Sea-Clusion, Virginia Beach
-
Price:
€253 - €358/night
€1,214 - €3,591/week
- Bedrooms: 6, sleeps 16
- Bathrooms: 4 Contact Manager
Sea N Stars, Virginia Beach
-
Price:
€231 - €316/night
€904 - €3,165/week
- Bedrooms: 6, sleeps 17
- Bathrooms: 4 Contact Manager
Sands of Time, Virginia Beach
-
Price:
€428/night
€1,905 - €5,668/week
- Bedrooms: 7, sleeps 16
- Bathrooms: 6 Contact Manager
Sandbridge Dunes 408, Virginia Beach
-
Price:
€158 - €293/night
€796 - €2,848/week
- Bedrooms: 3, sleeps 10
- Bathrooms: 3 Contact Manager
Seaward Sanctuary, Virginia Beach
-
Price:
€1,012 - €2,719/week
- Bedrooms: 5, sleeps 14
- Bathrooms: 3
- Min stay: 7 Contact Manager
A Promise Kept, Virginia Beach
-
Price:
€400 - €526/night
€1,766 - €5,252/week
- Bedrooms: 6, sleeps 18
- Bathrooms: 5 Contact Manager
Beach Bird, Virginia Beach
-
Price:
€855 - €2,705/week
- Bedrooms: 5, sleeps 18
- Bathrooms: 4
- Min stay: 7 Contact Manager
Recommended by Travelers
There are no vacation rentals within Chesapeake, Virginia. We broadened your search to include all rentals within 25 miles.
Shreveport, Virginia Beach
Nightly rate from
€328
€328
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 7, sleeps 16 |
| Bathrooms: | 5 |
Shreveport will delight your senses with its large decks and wide sandy beach. This great beach home offers MANY NEW UPGRADES FOR HER GUESTS TO ENJOY, ...
-
Nightly
€328 -
Weekly
€1,410 - €4,184 -
Monthly
--
Bountiful, Virginia Beach
Nightly rate from
€121
€121
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 12 |
| Bathrooms: | 3 |
You'll enjoy your "trip to Bountiful" at this tranquil, family and pet oriented house by the sea. Upgraded again in 2008 with new carpet, new living room ...
-
Nightly
€121 -
Weekly
€415 - €1,319 -
Monthly
--
Also consider
Virginia Beach Oceanfront 2Bdr Condo, Virginia Beach
| Management: | Verified owner |
| Property: | Condo/Apartment |
| Bedrooms: | 2, sleeps 6 |
| Bathrooms: | 2 |
Only two blocks south of the 24th Street Stage and the Old Coast Guard Station, Kamla Condominiums are in the heart of the Boardwalk, at the Virginia Beach ...
-
Nightly
-- -
Weekly
€646 - €1,187 -
Monthly
--
Sandbridge Dunes 210, Virginia Beach
| Management: | Professional |
| Property: | Condo/Apartment |
| Bedrooms: | 3, sleeps 8 |
| Bathrooms: | 2 |
| Min stay: | 7 |
Enjoy morning coffee and afternoon drinks overlooking the beach in this gorgeous oceanfront unit. Comfortable furnishings and beautiful views from the living ...
-
Nightly
-- -
Weekly
€1,546 - €2,206 -
Monthly
--
Also consider
Liquid Asset, Virginia Beach
Nightly rate from
€184
€184
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 10 |
| Bathrooms: | 3 |
So you want to mix a little pleasure with business? You'll find this newly re-modeled beach cottage property with central air/heating to have all the answers! ...
-
Nightly
€184 - €246 -
Weekly
€859 - €2,460 -
Monthly
--
Blue Moon, Virginia Beach
Nightly rate from
€231
€231
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 16 |
| Bathrooms: | 4 |
This excellent water view home is newly remodeled with space and privacy for several families with 2 bedrooms and a bath on either side of the spacious great ...
-
Nightly
€231 - €278 -
Weekly
€974 - €3,137 -
Monthly
--
Lazy Daze, Virginia Beach
Nightly rate from
€208
€208
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 16 |
| Bathrooms: | 3 |
Lazy Daze is a vacation home for an active family or a gathering of good friends. Spacious decks and screened-in porch, large in-ground pool w/basketball and ...
-
Nightly
€208 - €274 -
Weekly
€984 - €2,754 -
Monthly
--
Atlantic Sands, Virginia Beach
Nightly rate from
€301
€301
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 17 |
| Bathrooms: | 3 |
The song of sea sirens will call you back again and again to an exquisitely furnished beach retreat. This large, spacious home has multi-level decks for ...
-
Nightly
€301 - €379 -
Weekly
€1,277 - €3,797 -
Monthly
--
Also consider
Beachy Keen, Virginia Beach
Nightly rate from
€323
€323
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 16 |
| Bathrooms: | 3 |
This beachfront home is Beachy Keen! Great entertaining and quiet family living will be easily had with this nice floorplan. Gather your family and friends in ...
-
Nightly
€323 - €409 -
Weekly
€1,382 - €4,111 -
Monthly
--
Blue Heron, Virginia Beach
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 12 |
| Bathrooms: | 5 |
| Min stay: | 7 |
The Blue Heron is a beautiful home completed in the spring of 2007. It occupies a superb third row location with quick access to everything - a short path to ...
-
Nightly
-- -
Weekly
€1,134 - €3,368 -
Monthly
--
Straight to the Beach, Virginia Beach
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 7, sleeps 22 |
| Bathrooms: | 6 |
| Min stay: | 7 |
Grab your towel and head "Straight to the Beach!" This super comfortable beach cottage was completely remodeled! Spacious third floor with living area, full ...
-
Nightly
-- -
Weekly
€2,345 - €3,479 -
Monthly
--
Seaside Condo D-104, Virginia Beach
Nightly rate from
€95
€95
| Management: | Professional |
| Property: | Condo/Apartment |
| Bedrooms: | 3, sleeps 9 |
| Bathrooms: | 2 |
The low-key life of our coastal village is waiting for you at Seaside at Sandbridge.These condominiums, new in 2004, are just one block from the Atlantic ...
-
Nightly
€95 - €161 -
Weekly
€482 - €1,392 -
Monthly
--
Blue Lagoon, Virginia Beach
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 4, sleeps 10 |
| Bathrooms: | 2 |
| Min stay: | 7 |
Relax in this family friendly home located on the quiet North End of Sandbridge. Your children will enjoy the entertainment room as well as the kid friendly ...
-
Nightly
-- -
Weekly
€1,173 - €1,741 -
Monthly
--
Arcadia, Virginia Beach
Nightly rate from
€138
€138
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 7, sleeps 16 |
| Bathrooms: | 4 |
Simplicity is the spice of life at Arcadia. This home has everything you could want to please the beach goer. Enjoy close and easy beach access, take a dip in ...
-
Nightly
€138 -
Weekly
€768 - €3,287 -
Monthly
--
Also consider
Sun Settle In, Virginia Beach
Nightly rate from
€152
€152
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 13 |
| Bathrooms: | 3 |
Come settle in for a perfect week in this newly redecorated bayfront home. Gorgeous views of smoldering sunsets over Back Bay will be yours to enjoy from the ...
-
Nightly
€152 - €200 -
Weekly
€670 - €1,996 -
Monthly
--
Making Memories, Virginia Beach
Nightly rate from
€301
€301
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 16 |
| Bathrooms: | 5 |
REMODELING FOR 2009 INCLUDES: TILE FLOORING, REMODELED KITCHEN WITH STAINLESS STEEL APPLIANCES AND GRANITE COUNTERS, NEW INTERIOR PAINT AND CARPETING, NEW 42" ...
-
Nightly
€301 - €316 -
Weekly
€1,333 - €3,972 -
Monthly
--
Sea Breezes, Virginia Beach
Nightly rate from
€384
€384
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 8, sleeps 20 |
| Bathrooms: | 6 |
Beautifully decorated with fine furnishings and hand painted murals, Sea Breezes is the perfect choice for your family's beach vacation! Lots of front and ...
-
Nightly
€384 - €519 -
Weekly
€1,741 - €5,179 -
Monthly
--
Coastal View VII, Virginia Beach
Nightly rate from
€360
€360
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 6, sleeps 18 |
| Bathrooms: | 4 |
If you have never experienced a Coastal View home, you must try Coastal VII! This one will captivate you with its eagle's nest upper deck, offering views of ...
-
Nightly
€360 - €417 -
Weekly
€1,626 - €4,533 -
Monthly
--
Land Shark, Virginia Beach
Nightly rate from
€138
€138
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 11 |
| Bathrooms: | 4 |
Brand New, Never Before Rented! Completely remodeled and redesigned beach rental perfect for your family's summertime (or anytime!) beach vacation! Loaded ...
-
Nightly
€138 - €181 -
Weekly
€607 - €1,811 -
Monthly
--
Also consider
Wildest Dreams I, Virginia Beach
Nightly rate from
€290
€290
| Management: | Professional |
| Property: | Rental Home |
| Bedrooms: | 5, sleeps 14 |
| Bathrooms: | 4 |
Impeccable semi-oceanfront home will make all of your wildest dreams come true! Gorgeous pool with multi-level decks and jazzy cabana room with mini-fridge, ...
-
Nightly
€290 - €379 -
Weekly
€1,277 - €3,804 -
Monthly
--
-
-
Chesapeake Bay Waterfront
www.EasternShoreVacations.com Enjoy a Fun, Relaxing Weekend at St Michaels Area Waterfront Homes -
Chesapeake Condo Rentals
Marriott.ExecuStay.com/Chesapeake Chesapeake Furnished Apts for 30+ Nights. Enjoy Free WiFi & More. -
Aloft Chesapeake
aloft.StarwoodHotels.com/Chesapeake Official Aloft Chesapeake Hotel Site. Member of the SPG® Program. -
Tysons Corner Apartments
www.dwoskin.com Apartments as low as $1100 per month in Tysons Corner Virginia!
-
Chesapeake Bay Waterfront
- View all deals for Chesapeake
- Sponsored links *
Professionally managed typically means…
- Member of the FlipKey Verified Property Manager program
- Dedicated on-site help
- Experienced local staff
- Professional hospitality services
- Secure credit card payment
Verified Plus property owner typically means…
- Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
- Established history of renting online
- Direct & personal contact
- Detailed rental knowledge
- Flexible dates & rates
- More options in smaller towns
Verified property owner typically means…
- Verification of owner name and address via valid credit card
- History of renting online
- Direct & personal contact
- Detailed rental knowledge
- Flexible dates & rates
- More options in smaller towns
© 2009 TripAdvisor LLC All rights reserved. TripAdvisor Terms of Use and Privacy Policy.
* TripAdvisor LLC is not a booking agent and does not charge any service fees to users of our site... (more)
We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.
TripAdvisor LLC is not responsible for content on external web sites. Taxes, fees not included for deals content.