Cottage vacation rentals in Hampton Roads

Peaceful beach @Courtyard Cottage Pets Allowed

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.

“Magnolia Cottage” on the River

Perched on a bluff high above the James River this charming rehabbed cottage is an idyllic escape from everyday life. This spot is for travelers who seek a step back in time to a simpler life. You’ll be surrounded by woods, water and a growing flower farm. The set up is unique in that the cottage itself holds living and sleeping space while your own designated bathroom and outdoor hot water shower are a short walk across the yard to a tool shed turned luxury bath and shower under the open sky.

902 CH Carriage House 20 Steps to Beach & Specials

902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Beachfront Grilling. Specials - Free Kayaks/Paddle-Boards/Beach Chair & Beach Umbrellas starting September 8 Step back in time at the Historic Carriage House, a beautifully restored 120-year-old gem just 20 feet from the Chesapeake Bay. Once home to horses and rowboats in the early 1900s, this 1-bedroom, 1-bath carriage house now blends timeless charm with modern comfort — offering guests a truly unique and peaceful bayfront getaway.

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 ****

Coleman Cottage

Enjoy easy access to everything from this perfectly located home base. This recently updated cottage is steps away from our local farmers market and a short ride to all that Williamsburg has to offer. Walking distance to local grocery store and local restaurants. Minutes drive to Colonial Williamsburg, Jamestown Island, Billsburg and other outdoor breweries. William and Mary is minutes away. Newtown shops and restaurants is a short drive. Bush Gardens is a 10 minute drive

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.

Sarah's Creek Starlight

Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

The Cottage on Sarah's Creek

Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

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.