Holiday rentals in Cambridge

Nature's Rest in Church Creek

Nature's Rest is located just minutes from Blackwater Wildlife Refuge, The Harriet Tubman Museum, Blackwater Adventures! Boat ramps are close by for easy access to the Chesapeake Bay and its tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Historic 1740 Home Near Waterfront

Guests will be steps away from the historic district and marina when you stay at the oldest home in Cambridge! You will step back in time with the home’s unique history. Enjoy the views of High Street and Choptank River from the rocking chairs on the beautiful upper and lower front porches with a cup of coffee. After exploring the rooms and passageways, find a comfortable nook to relax and unwind. There are plenty of reasons to come stay in this charming home and visit Cambridge! Pet friendly.

High Water Guest House

Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of historic High Street and adjacent to the city marina. Walk to downtown for shopping and dining. Take advantage of having a front row seat to the finish line of Ironman Maryland. Beach, pier and large yard made available for your use. Two inflatable paddleboards, one inflatable kayak and one inflatable 2 seater kayak available for use. Limited size life jackets available.

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

The Place in Cambridge-Summer is here!

Beautifully located, a clean crisp poolhouse cottage with key extras.! Queen bed, full kitchenette, and beautiful bath. Enjoy the lovely in-ground pool & poolside seating ( open May 1st - Sept. 30th) Perfect for couples or small families. A block from the Choptank River, 1/2 mile walk downtown to shops and dining. Experience the Eastern Shore of the Chesapeake from a new perspective-it's your stay! The Place in Cambridge, sometimes, the best experiences come in simple packages.

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

Osprey's Retreat Waterfront w/ private beach/dock

Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

School Street Retreat: Cozy, artsy, central home

School Street is the perfect spot to launch adventures around Cambridge and the Eastern Shore. You get a full house with two bedrooms, two full bathrooms and beautiful native gardens. Just blocks from Great Marsh Point for boating, fishing, play and river access. Less than a mile to downtown historic Cambridge and the lighthouse/market. Quick drives to Easton, Vienna, Blackwater and more. Also provides great access to historic sites in the area. Come rest, relax and explore!

Large 3 BR in Historic Cambridge

Come visit Historic Cambridge, MD and stay in a spacious and timeless home. We are walkable to downtown Cambridge for any shopping/dining. We are a kid-friendly, dog-friendly host that enjoys everything Cambridge has to offer. We can accommodate larger groups and multiple families, our best friends own the home next door and is also listed on AirBNB. If you have a larger group don't hesitate to reach out as we can assist with coordinating side by side homes for your stay!

Charming cottage, FP, 1 blk water, historic area

A peaceful oasis near the water in the center of Cambridge. Tucked away at the end of a cul-de-sac with historic connections, this private, charming antique-filled cottage is steps away from the river. Enjoy three comfortable bedrooms all with en-suite bathrooms, and 2 living areas w/ fireplace and view of the Choptank River, with plenty of room for family and friends to entertain. Close to all amenities, Gerry Boyle Park and the waterfront.

Aurora Blue - A Stylish Experience

A stylish experience at this centrally-located retreat. The reviews are coming in... guests love this home! New owners purchased and renovated the entire home both inside and out. Enjoy the close proximity to the Choptank River & Cambridge Creek, Rt 50, and the downtown area. The owners have renovated and furnished this house with all top of the line, brand new, modern appliances, furniture, and linens.