Cottage holiday rentals in Chesapeake

Comfy three bedroom cottage - easy beach access

Enjoy the beach at our Willoughby Spit beach house. Located across the street from the beach and only 1/2 block to the beach access. You will have the entire house & property for you and your family - no shared walls, no assigned parking spaces, no shared washer and dryer. We have three outside decks for grilling and relaxing with family and friends. Our kitchen is fully stocked including KitchenAid mixer and food processor, Ninja blender, Crock pots, coffee maker, toaster and waffle maker.

Cozy Cottage - NEW hot tub, dogs OK, fenced yard

Welcome to Wayland Beach Cottage, your home away from home! Here are some of the things you can look forward to: - queen beds - smart TVs in each room - fully equipped kitchen & laundry room - fully fenced backyard - 6-person hot tub *new!* - outdoor seating under a pergola - 4-burner gas grill - long, private driveway - speedy Wi-Fi We're nearby to so many fun things to do, shop, and eat! Bring the family, see the sights, and come relax at Wayland Beach Cottage. We'd love to have you!

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

Positano Villa

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.

The Beach Nest. Walk to oceanfront.

The Beach Nest is a pristinely clean cottage located just a half-mile walk from the oceanfront and boardwalk. The cottage is well-outfitted with beach chairs, beach cruisers, beach towels, a beach cart, and a sand umbrella. A quaint retreat ideal for two. The Beach Nest is NOT a party house. SMOKING IS PROHIBITED. PETS ARE NOT ALLOWED as we often host guests with allergies.

Seaglass Cottage

Brand new, sparkling clean, "Seaglass cottage" in a quiet, beach neighborhood! Two blocks from the exciting, artsy, "VIBE" district, with murals, marketplace and unique restaurants. Five blocks from the active, Virginia Beach Boardwalk with shopping, music and dining! Don't do the usual, hotel lobbies and crowds, come to a clean place that you can call your own!

Enchanted Holiday Cottage

Our charming little bungalow reminds us of the fairy tales of our childhood. The history of the surrounding area is utterly fascinating, and worth learning about. 5 min. drive to Colonial Williamsburg, 1 queen and 1 full bed in two distinctly charming bedrooms.