Vacation Rental Homes

Experience coastal living at its finest in this meticulously preserved 1913 four-square home, perfectly positioned between Cape Charles'most coveted attractions. Just a leisurely one-and-a-half block stroll takes you either to the pristine beaches of the Chesapeake Bay or to the vibrant town park, where summer concerts, tennis matches, and recreational activities create a symphony of community life.

This distinguished residence, graced by Crepe myrtles that line its tranquil street, offers an elegant blend of historic charm and modern comfort. Four well-appointed bedrooms and one-and-a-half bathrooms provide ample space for both family living and gracious entertaining. The home's refined character shines through in its gleaming wood floors, while the upgraded kitchen boasts contemporary appliances for the discerning chef.

Outdoor living reaches new heights with both covered front and back porches, perfect for morning coffee or evening relaxation. The piece de résistance is an elevated screened gazebo nestled in the fenced backyard, accompanied by custom decking that creates an ideal setting for al fresco dining. Practical amenities include an outdoor shower for post-beach rinses and a dedicated fish cleaning station with sink – a nod to the coastal lifestyle.

Convenience meets charm with flexible parking options, including space for two vehicles via the rear alley access, complemented by ample street parking. Situated in the historic district, this home offers privileged access to Cape Charles' boutique shopping, dining, and cultural attractions, making it an ideal residence for those seeking a sophisticated coastal retreat.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $200 will apply. Pet restriction: One small to medium size adult dog under 50 lbs, must be housebroken. NO CATS. All pets must be disclosed prior to arrival.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab at the waterfront Memorial Park. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel! The second bedroom has two twin beds and you'll find another full bathroom upstairs as well. Come and see for yourself! (Waterfront areas, dock, pier and playground area pictured are public property/Memorial Park.)

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Welcome to a waterfront townhome retreat that delivers island living with a front-row view of the lighthouse and sunrises that will surely outshine your alarm clock. Set in one of Chincoteague Island’s most desired areas, this pet-friendly 2-bedroom, 2.5-bath home pairs comfort, charm, and a little vacation energy in all the right ways.

Inside, the layout offers easy everyday living and inviting spaces to unwind after a day on the water or at the beach. The living room is anchored by a 75-inch television, perfect for movie nights, game days, or simply pretending you are “just resting your eyes.” Upstairs, the primary bedroom features a private bathroom and a waterside balcony, creating a peaceful retreat for morning coffee, evening breezes, and uninterrupted water views. A second bedroom and additional baths provide flexibility for guests, work-from-home needs, or both. The extra half bath adds convenience for entertaining, while the townhouse design keeps daily vacationing practical and fun. 

Outdoor living is just as appealing, with a fishing and crabbing pier that invites relaxed afternoons and fresh catches, plus a hot and cold outside shower for easy cleanup after beach trips. Imagine casting a line at dusk, then rinsing off before dinner as the water glows around you. You are also conveniently close to Maui Jack’s Waterpark and Assateague Beach, so fun is never far from home.

If you have been searching for a vacation spot that feels equal parts coastal escape and everyday comfort, this one checks all the boxes. Book today and see why this waterfront townhouse is easy to love.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 will apply. Maximum pets allowed: 1. All pets must be disclosed prior to arrival.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Welcome to 'Counting Corks' (formerly known as 'Smith Beach Pines'), the moment you step foot in this beautiful waterfront cottage you feel at home. The pet friendly cottage is 1,150 sq ft, featuring 3 bedrooms and 2 full baths. The primary bedroom has a king size bed and TV. On the other end of the home the second bedroom features a queen bed and a TV. The third bedroom features a twin over a full bunk bed. The cottage also has a bar room leading into the deck area, with plenty of seating to entertain. The dock leads to the creek and is just waiting for you to go crabbing, fishing, or kayaking or simply enjoy the beautiful sunrise while drinking a cup of coffee. The property is a short distance to the community beach and to the community boat ramp. Also features an outdoor shower and a firepit area with plenty of seating. The cottage is located just a few short miles from the Historic Town of Cape Charles and about 25 minutes from Kiptopeke State Park.

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 2.  All pets must be disclosed prior to arrival.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the "Beach Road." Come and check it out for yourself!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.