Vacation rentals in Dorchester County

A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.

4.99 out of 5 average rating, 171 reviews

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.

4.97 out of 5 average rating, 30 reviews

A pair of glass French doors provides a view of the outdoor seating area and pool. Bright red chairs are positioned around a fire pit on a stone patio, framed by a lush green lawn leading to the water.

Home in Tilghman Island

Relax by the Water - Summer Dates Available!

STRN-24-62. Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacation experience. Fabulous location with panoramic views of the water everywhere you look. Crab and fish from the dock. Hop on a bike and explore the island by land and then try out kayaks for a water adventure. Cool off with an afternoon dip in the pool. Enjoy starry nights at the waterfront firepit. If the bikes and kayaks wore you out relax your muscles in the hot tub. Perfect!

4.99 out of 5 average rating, 83 reviews

Cabin in Lusby

Your own private beach? Horizon views of the bay?

Beachfront modern updated Panamabode log cabin with gorgeous views from the home, the hot tub, fire pit, lawn, kayaks. Sit on the swing and watch your family play in the sand on the beach or in the shallow water. Water usually about 3-4' feet for quite a way out. Eagles, pelicans,hummingbirds zoom by, dolphins,crab&oyster boats... Bring your own bed linen & towels (see below for sizes.) No pets allowed at any time. No additional guests or visitors. Limit 3 cars (parking on driveway only.)

5 out of 5 average rating, 14 reviews

A covered porch with a vaulted ceiling features comfortable blue seating arrangements and a dining table, all overlooking tranquil waters. Large windows allow for panoramic views of the Cambridge Creek, while a ceiling fan provides a gentle breeze.

Guesthouse in Cambridge

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. Bring your kayak, paddleboard, or boat and enjoy all Cambridge has to offer or just sit on the end of the pier to watch the sunrise or sunset.

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

4.94 out of 5 average rating, 132 reviews

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.

4.95 out of 5 average rating, 477 reviews

Guest suite in Cambridge

Sailwinds Waterview Loft at Cambridge Creek

Waterview second story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located just 4 blocks from Route 50 and only 2 blocks from the Choptank River! This amazing space is within walking distance to seafood restaurants, shops, public boat ramp, beach, and parks! Close to all local attractions including the Choptank River Lighthouse, Sailwinds Park, Harriett Tubman UnderGround Railroad, Blackwater Refuge, Eagleman/Iron Man, and so many more!

A serene neighborhood view is presented, featuring a well-maintained pathway bordered by gardens. Lush greenery and trees provide shade, while charming homes are visible across the street. The scene captures a tranquil atmosphere that invites leisurely exploration.

5 out of 5 average rating, 14 reviews

"Riverside Retreat"

Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview rental is the perfect home base for exploring all that this fascinating city has to offer. With its rich history, vibrant culture, and stunning natural beauty, Cambridge is an ideal destination for relaxation and exploration. Within walking distance to great restaurants, shopping, marinas and a historic downtown area that will both entertain and delight you!

Apartment in Lexington Park

A shaded outdoor deck overlooks the calm waters of the St. Mary's River. Two lounge chairs with navy fabric face the water, positioned beside a small table. The surrounding railings and scenic view provide a serene space for relaxation.

5 out of 5 average rating, 374 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

4.96 out of 5 average rating, 162 reviews

A wooden pier extends over calm water, leading to a two-story home with large windows and a welcoming deck. Brightly colored chairs sit in the yard, alongside a grassy area and trees. Two kayaks are visible on the pier, ready for use.

Home in Lexington Park

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.

4.98 out of 5 average rating, 126 reviews

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!

4.92 out of 5 average rating, 12 reviews

A three-level bay house is showcased, featuring a large screened deck and wraparound balconies. The exterior is composed of light-colored siding, complemented by green trees surrounding the property. Stairs lead up from the ground level to the entrance, enhancing accessibility to the upper levels.

Home in Lusby

Chesapeake Bay Waterfront View

Indulge in your dream vacation at our one-of-a-kind bay house! This three-level home offers unmatched water views that will captivate you. Strategically located 15 min away from Solomons Island, for a city escape, with exclusive access to 2 private sand beaches and a lake. Our home is a delight, a blend of comfort, fun and tranquility. Highlights: Breathtaking Water Views Gourmet Kitchen Screened Deck Private beaches