Guest house holiday rentals in Dorchester County

Cozy Guest House Near Park

This lovely guest house is located in the historic district of Cambridge within 3 blocks to the Great Marsh/Gerry Boyle waterfront park. This cozy space includes a full kitchen with dishes, living space with reclining sofa, new Bedstory med/firm queen bed separated by an antique armoire as well as a large bathroom. You will have a private parking area and separate entryway through a private courtyard. Less than 1 mile to historic Cambridge. Near start of annual races and waterfront activities.

Blue Crab Bungalow

​Our charming, remote bungalow allows you to relax, refresh, and truly unwind while taking in views of the bay. Enjoy amazing sunsets, starry nights, and the water view from the second-story deck, private pier, or around the fire pit. ​Try crabbing or fishing from the pier—no license needed! ​A small, local beach for swimming and a public boat ramp are less than 5 minutes away. We are a little over an hour from Ocean City, Chincoteague, Assateague, and the Blackwater National Wildlife Refuge.

Heide's GuestHouse

Pairing modern comforts with timeless charm, this 1-bath studio offers an ideal stay on your next visit to coastal Cambridge. Visit the Harriet Tubman Museum, dine on fresh local seafood, or enjoy a leisurely stroll along the Choptank River — all just steps from your front door. Back home, rest and relax on the shared patio, or curled up in front of the TV. Traveling with a pet, or maybe a larger crew? Make use of this vacation rental's pet-friendly policy and additional rental home on-site.

El Camino

Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet, waterfront oasis guesthouse is the perfect weekend retreat. There is 1 bedroom and 1 bathroom in the house. There is also a pullout couch. There is a large dock for hanging out / sunbathing. There is not a full kitchen, but there is an outdoor grill. You are surrounded by nature - this is a true escape! If you're looking for the perfect weekend getaway, this is it! *Wifi is spotty! Do not rely on it!*

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.

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.

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.

Cozy Waterfront Garage Unit

Peaceful 1BR waterfront retreat with stunning views—perfect for relaxing or exploring the Eastern Shore. Enjoy crabbing, fishing, kayaking, or unwind on the private deck. Features a queen bedroom, pull-out sofa, full bath, kitchenette, and washer/dryer. Just minutes from downtown Cambridge, Blackwater Refuge, shops, and dining. Ideal for couples, solo travelers, or small families. Only 15-20 minutes from Cambridge, and 10 mins from Blackwater and Harriet Tubman Museum.

Nanticoke river front Studio!

Relax in our cozy river front apartment suite. The apartment is located in our stand alone garage next to our primary residence facing the beautiful Nanticoke River. Perfect for kayaking and exploring nature. Centrally located between popular Eastern Shore destinations, like Ocean City and many historic small towns. Take this opportunity to explore all there is to see in the area, or relax and take in the many wildlife activities that can be seen along the river.

Camelot Cottage

Camelot Cottage, a charming small cottage nestled in the woods, exudes a peaceful and serene atmosphere. It offers a private and secluded retreat, surrounded by landscaping that captivate the senses. As you sip your early morning coffee, you may see deer or turkeys passing by the window. The cottage can accommodate a 3rd person, however, due to the small area, its suits 2 most comfortably. I have a mattress I can set up prior to your arrival if needed.

The Loft at Sailor's Retreat. Waterfront Apartment

Romantic waterfront loft for couples in a charming barn. Relax in a cozy king bed, enjoy a full bath, and cook in a well-equipped country kitchen. Sip wine or coffee on your private balcony overlooking the water, or explore the creek with kayaks and paddleboards. Share the pool (Apr–Oct), lawn games, and game room with one other unit. Perfect for a peaceful getaway to unwind and reconnect. Designed as an adults-only retreat—no children please.

Newly Renovated Guest House

Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Maryland. The house is in a quiet neighborhood with a beautiful view of Town Creek. Take a short walk or bike ride to town where you can enjoy fine dining and shopping. The house is equipped with TV, Wifi, AC to make your stay comfortable. There is reserved parking in front of the house and enjoy dining on the outside porch.