Beachfront vacation rentals in Chesapeake Beach

Oceanfront Building Boardwalk Pool Beach 3 Beds

Welcome to the Cozy Crab – updated, comfort-focused & steps from the sand! Located in a quiet corner of a beachfront building on the Virginia Beach boardwalk with a seasonal pool (open mid-May–mid-Oct). Sleeps 4 with 3 real beds: one queen and two singles, all with real mattresses. Features a large, updated bathroom with full vanity and a kitchen. Just a few steps up—no elevator needed. No chore checkout, pro cleaning, fresh linens/towels, WiFi. 2nd-floor grills. Eat! restaurant is downstairs!

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

Poseidon - Beach Carriage House - 120 Years Old

Your Bayfront Vacation Spot. If you want to spend good family time, a romantic getaway, or live in a cool place while working here, this is your spot. Our neighborhood is located on the shores of the historic Chesapeake Bay. Step onto our beach and you will see that we are the perfect spot for sunrises/sunsets, fishing/crabbing, sunbathing, grilling & hot tubbing. The rental isnt on the beach-side of the property so walk around the building to the beach which is only 30 feet away.

Private Beach Access at The OV Beach House

Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided. Can accommodate up to 8 people.

New Beach Home on the Chesapeake Bay

New Beach House on the Chesapeake Bay. Entire 2500 SF Home, 1st, 2nd and 3rd floors. Three King size bedrooms, third floor with 2 Sofa Beds. One Full kitchen and one Kitchenette. House on the dune 40 steps to the sandy beach. Balcony view of bay for sunrise coffee & sunset wine. New & old homes surround this newly built home in "East Ocean View." Restaurants short walk, more only a two min. drive. Summer Sailing regattas on Weds. and Sun. evenings, live music at the Pavilion.

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Villa Positano

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay