Cottage vacation rentals in Chesapeake

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.

The Seaglass Cottage by the Chesapeake Bay

The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.

The Little House on Park Avenue

Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

Sanctuary on Sandpiper - Bayfront in Sandbridge

Relax in this renovated 1950's flat-top beach cottage in gorgeous Sandbridge Beach. This waterfront home, on a canal off the beautiful Back Bay, is an easy five-minute, two-block walk to the ocean and the perfect setting for your family beach vacation. With three king beds, a custom-built bunk room, two full baths, a well-equipped kitchen, a spacious backyard, saltwater pool, and all linens and beach gear included, it's got everything you need to spend quality time away with your family.

Quaint 2 Bedroom Cottage in Chicks Beach

This 2 bedroom 1 bathroom quaint cottage is the perfect small family getaway. Located 2 residential blocks to the beach. The beach is great for families with children. This unit is connected to a 1 bedroom rental. Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $100 pet fee with pre approval. ***Summer 2026 check in on Friday only ****

Cozy Cottage w/ Hot Tub, Pool Table, Fenced Yard

Welcome to Wayland Beach Cottage, a relaxed beach retreat with your own private hot tub and separate game room. Unwind under the pergola, soak year-round in the 6-person hot tub, or enjoy movie nights and friendly competition around the full-size 8-foot pool table in your own entertainment space. With a fully fenced yard, smart TVs throughout, fast Wi-Fi, a long private driveway, and easy access to beaches and dining, it’s the perfect getaway for families and friends.

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.

Comfy three bedroom cottage - easy beach access

Enjoy a multi mile beach that feels private most of the year at our Willoughby Spit beach house. We are located across the street from the beach and only 1/2 block to the beach access. You will have the entire house to yourself - no shared walls, no assigned parking spaces, no shared washer and dryer. We have three outside decks for grilling and relaxing and our kitchen is fully stocked with complimentary coffee, wine and snacks.

Walk-to-Beach Apt with Shared Pool

Escape to The Old Beacon, Unit 2! This 1940’s upstairs surfer nest was updated in 2021 with stylish accents and is an Airbnb private retreat favorite! Located just two blocks from the Virginia Beach boardwalk. Perfect for 1 or 2, it features a modern kitchen, dedicated workspace, and access to a shared pool and fire pit. Enjoy the best of the oceanfront in this cozy, well-appointed space that comfortably fits up to 2 guests.

Life on a Sandbar right on Chesapeake Bay

Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!

Beachfront stay with kayaks & paddleboards

Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.

The Ladybug - arcade, dog-friendly, firepit, & EV

A peaceful, design-forward farmhouse minutes from Cape Charles where vintage fun meets smart-home comfort. Enjoy a private arcade, Peloton gym, EV charger, firepit sunsets, and whole-home Spotify sound. Guests love the vinyl collection, chef’s kitchen, and views of the Magothy Bay Preserve. Relax under wide-open skies by the firepit or start your day on the Magothy Bay trails.