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Chesapeake Beach Vacation Rentals

Cottages, Houses and Condo Rentals in the Chesapeake Bay Area

The Chesapeake Bay area beaches of Virginia offer vacationers bay-front and bay-side houses and cottages ranging in size from two to six-bedrooms. There are a wide variety of styles and options to choose from including a vast array of amenities. Pet-friendly options are available.

We also have rentals in The Resort Area, Croatan Beach, and The North End or browse through all properties at once.

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7 properties were found meeting your search criteria.

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Jefferson Avenue 3852

If you’ve dreamed of a summer vacation to remember for a lifetime, this is it! Panoramic views of Chesapeake Bay spanning from Cape Henry to the Bay Bridge Tunnel, all from the expansive 35 x 15 f 2nd floor deck of this gorgeous bay front property. Private beach access from your back door leads to a restful and less crowded beach experience. Nothing like this home is available on the bay anywhere in Virginia Beach and is located in a semi-private bay front community with their own July 4th fireworks show that beats the city display! This 3500 square foot single family home is filled with c...more info
        
Location: Bay Front

Property Type: Single Family

Sleeps: 12   Bedrooms: 3

Baths: 3   Half: 1 

Pets: No  

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Ketch Court 2411

CA, W/D, DW, microwave, jenn-aire grill, phone, cable TV, 2 decks, ceiling fans, H/C outside shower, 1 step off the deck onto the beach. BR1: king, BR2: queen, Br3: queen, BR4: queen, BR5: double, queen sleep sofa in the LR. All properties are nonsmoking and have a 7 Night Minimum starting on Saturdays. If properties include pets & linens, it will state under the Amenities Tab. (Linens & towels are NOT included during the OFF SEASON)
        
Location: Bay Front

Property Type: House

Sleeps: 10   Bedrooms: 5

Beds: King, 3 Queen, Double

Baths: 3  

Pets: No  

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Lone Pine Point 2509

Gorgeous bay front 5 Bedroom, 4 Bath Single Family Home that sleeps 15 people. This property walks out onto a large porch that overviews a dock. This will give you access to jet skis as well as a fishing boat that comes with its own captain. This large 2 story home has 4 bedrooms on the 2nd floor, 1 bedroom on the 1st floor, & its own Mother In-Law Suite on the 1st floor. Mother In-Law Suite walks out to the side of the house where you can enjoy the sitting area with a tree swing. Beautiful open fully equipped kitchen, Wireless Internet, Washer/Dryer, Cable TV with VCRs & DVD players, Charco...more info
        
Location: Bay Front

Property Type: Single Family

Sleeps: 15   Bedrooms: 5

Beds: 1K, 2Q, 4S, 3 Trundles

Baths: 4  

Pets: No   Parking Spots: 4

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Bayberry 2310

CA, W/D, DW, 2 microwaves, telephone, 3 cable TV's, VCR, wireless internet, outside shower, charcoal grill, 2 decks, 2 enclosed porches, extra fridge, new carpet, ceiling fans, beach chairs, cooler with wheels, 2 picnic tables, baby high chair, baby gate, upstairs family room has a 50" TV, eating areas on both enclosed porches, great views of the bay, less than 50 feet from the beach. BR1: queen on 2nd floor, BR2: 1 queen & 1 single on 2nd floor, BR3: queen on 1st floor, BR4: 2 singles on 1st floor, LR: double & trundle on 2nd floor, LR: double sleep sofa on 1st floor. All properties are no...more info
        
Location: Bay Side

Property Type: House

Sleeps: 13   Bedrooms: 4

Beds: 3Q,3Single,Daybed,Trundle,DSS

Baths: 3  

Pets: No  

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Powhatan Avenue 2265

CA, DW, W/D, DVD player, wireless internet, deck, gas grill. Located on the Chesapeake Bay. Minutes from the Chesapeake Bay Bridge Tunnel & 20 mins from the resort area. BR1: Queen, BR2: Pyramid Bunk, LR: Queen Sleep Sofa All properties are nonsmoking and have a 7 Night Minimum starting on Saturdays. If properties include pets & linens, it will state under the Amenities Tab. (Linens & towels are NOT included during the OFF SEASON)
        
Location: Bay Side

Property Type: Cottage

Sleeps: 6   Bedrooms: 2

Beds: Queen, Pyramid Bunk, QSS

Baths: 1   Half: 1 

Pets: No  

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Powhatan Avenue 2267

CA, DW, W/D, DVD player, wireless internet, gas grill. Located on the Chesapeake Bay. Minutes from the Chesapeake Bay Bridge Tunnel & 20 mins from the resort area. BR1 on 2nd FL: king, BR2 on 2nd FL: Pyramid Bunk All properties are nonsmoking and have a 7 Night Minimum starting on Saturdays. If properties include pets & linens, it will state under the Amenities Tab. (Linens & towels are NOT included during the OFF SEASON)
        
Location: Bay Side

Property Type: Cottage

Sleeps: 6   Bedrooms: 2

Beds: King, Pyramid Bunk, QSS

Baths: 1   Half: 1 

Pets: No  

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W. Great Neck 2325, unit 202

Your family will love this condo located just a short 1/2 block away from the Bay beach. Enjoy amazing views of the Chesapeake Bay from the shared upper deck. Easy access to bay beach at end of street, two covered parking spaces. BR1: Queen BR2: Queen, Double Futon LR: Double Sleep Sofa All properties are nonsmoking and have a 7 Night Minimum starting on Saturdays. If properties include pets & linens, it will state under the Amenities Tab. (Linens & towels are NOT included during the OFF SEASON)
        
Location: Bay Side

Property Type: Condo

Sleeps: 8   Bedrooms: 2

Beds: 2 Queens, Double Futon, DSS

Baths: 2  

Pets: No   Parking Spots: 2

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SunMonTueWedThuFriSat
2627282930311
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SunMonTueWedThuFriSat
2627282930311
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9101112131415
16171819202122
23242526272829
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June 2013
SunMonTueWedThuFriSat
2627282930311
2345678
9101112131415
16171819202122
23242526272829
30123456
June 2013
SunMonTueWedThuFriSat
2627282930311
2345678
9101112131415
16171819202122
23242526272829
30123456
June 2013
SunMonTueWedThuFriSat
2627282930311
2345678
9101112131415
16171819202122
23242526272829
30123456
June 2013
SunMonTueWedThuFriSat
2627282930311
2345678
9101112131415
16171819202122
23242526272829
30123456
June 2013
SunMonTueWedThuFriSat
2627282930311
2345678
9101112131415
16171819202122
23242526272829
30123456
June 2013
SunMonTueWedThuFriSat
2627282930311
2345678
9101112131415
16171819202122
23242526272829
30123456
= Available
= Booked