Waterfront holiday rentals in Cambridge

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

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

Gorgeous, waterfront home - Perfect for Families.

If you were thinking of heading to the Eastern Shore, Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all. First Floor bedroom, also.

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!