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Peach Perfect | Chesapeake Properties

An amazing in town location on a tree lined street, that will book quickly! This beautifully renovated Victorian home has all the modern updates that meet period charm! Peach Perfect, Home Features: • 2 Bedroom, 2.5 Bath - Available for up to 6 Guests! • Modern Gourmet Kitchen • Cape Charles art by Eastern Shore artists • Stereo System, Games & Books • Free WiFi & Smart TVs Please SEE: Other Things to Note For Area Details, Please SEE: Where You'll Be (Located under the map!) This is a no pe

Restored 1930’s Tiny Home 3 min to Cape Charles

Step into Cape Charles history when staying in this newly restored 1930’s tiny home! The vintage series of tiny homes is one of 10 located in the 4-acre community. The home features a queen-sized bed with plenty of room for 2 guests, a full bathroom, microwave, mini fridge, coffee pot, a Smart TV, a private porch & access to the largest firepit you may ever see! Enjoy all that Cape Charles has to offer, while being immersed in the history that has allowed the city to grow into what it is today!

Family Reunion on the Bay

Unpretentious, clean & family-friendly. Bright open-plan for easy living. Generous seating throughout. Loads of games, toys. Ideal for extended families. Side-door ramp, 1st-floor ADA bedroom, step-in shower w/seat & grab bar nearby. Backyard fire pit, picnic tables, grill, corn hole. Free firewood, propane, stand-up paddleboard, beach chairs. 3 IMPORTANT NOTES: 1. bedrm #5 reduced to 4 beds in 2026 2. Absolutely NO PETS ALLOWED! ($750 fine) 3. Only 7-day Sat.-to-Sat. rentals June thru Aug. 30.

Three Little Birds-Kayak, fish, bike, enjoy!

We have a wonderful waterfront location with a handicap accessible studio suite, huge accessible bathroom, and PRIVATE ENTRANCE! We live on site and are around to help should you have any questions or concerns, but you will of course have complete privacy in your suite. Outside we have a dock, complete with fire pit, fishing gear, binoculars, bird watching guide, raft, and kayaks! We have bikes available upon request. The location is close to various attractions including the beach!

*Grotto Waterfall* Bethel Oasis | 2masters | 5bdrs

Built in 2019, our home was designed to make our guests' stay enjoyable. In 2023 a Grotto waterfall feature was added with surrounding 3-foot pond. There are two master bedrooms with walk-in showers, as well as a lovely play set in the back yard. The 1st floor master closet was converted into a simple nursery with a crib and baby swing. The master bedroom on the 2nd floor has a queen size bed for parents and a space dedicated to toddlers, featuring a princess castle bed.

Sweet Bay | Chesapeake Properties

Situated by the shore of the Chesapeake Bay within the private Bay Creek community and historic Cape Charles. Just a short walk to a beautiful exclusive 2 mile beach! Please SEE: Other Things to Note For Area Details, Please SEE: Where You'll Be (Located under the map!) *This is a no pet/animal home. *See "The Space" for Bay Creek amenities information (complimentary) and Bay Creek's Life Center access information (fee applies).

Sojourn's Harborage 2 BR 1 BA

Enjoy a relaxing beach vacation in the fully renovated, OV Harborage Suite. This modern 750 sq. ft. 2-bed/1-bath condo on the 1st floor offers comfort and style. Shared spaces include fire pits and ample seating. Please note, ongoing city construction may cause noise during business hours and significant water pooling in 5th bay. For more details, feel free to contact us before booking.

Coastal Charmer | Chesapeake Properties

Coastal Charmer - 4 bedroom, 2 bath, sleeps 8-10 with 2 sets of bunk beds. - Completely Renovated! Cozy and comfy interiors, with an amazing backyard for outdoor dining or relaxing under the stars around the stone firepit! Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *This is a no pet/animal home.

Seagrass | Chesapeake Properties

Just steps away from the beach, "Seagrass" is situated on a corner lot on the town's beautiful tree lined street! Spacious 3 bedroom, 3 bath duplex with lots of curb appeal! Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet.