Holiday rentals in Callaway

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Beachfront Oasis with Amazing Views

Perfect getaway home to relax and enjoy peaceful beach views. This beachfront home is perfect for a romantic weekend getaway or a family vacation. Enjoy long walks on the beach, conversations at the fire pit in the evening, kayaking or hunting for fossil sharks teeth. The perfect escape from DC, the home is just over an hour from the city and located in the quiet, private beach community.

Spectacular beachfront walk-out in Piney Point MD

A beautiful 1000ft private beachfront walk-out to be enjoyed couples, families and even your pet. If you're interested in an incredible beach sanctuary, birds, turtles, kayaking or just reading a book listening to the waves - our sanctuary is your sanctuary. Please join us!

Waterfront Fishing, Game Room, Kayaks, Firepit

Escape to your dream vacation at this 3-4 bedroom waterfront retreat on the peaceful Corrotoman River, where everyone can unwind and enjoy ample space. This idyllic getaway offers a perfect mix of relaxation and adventure, ideal for family and friends alike.