Pet-friendly holiday rentals in Southern Maryland

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Pets · Outdoor spaces · Kitchen

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Outdoor spaces · Pets · Cleanliness

The River House: A private waterfront oasis…

Cozy up by a roaring fire with your partner and relish the winter chill! This private waterfront retreat offers panoramic water views of the Potomac River and sits at the mouth of Breton Bay. At the end of the road and occupying two acres, the property is a private oasis of year-round natural beauty. You’ll have 650’ of waterfront to yourself to lounge at the waterside tiki-bar deck, on the screened-in porch, on the house deck, in the yard or on the hammock. Kayak, canoe, chill however you like!

Outdoor spaces · Pets · Bathroom

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

Pets · Walkability · Kitchen

Hot Tub Hideaway by Shark Tooth Shores

With views of the Chesapeake Bay, access to private beaches, a brand new hot tub, air hockey table, kayaks, and being just minutes away from hot spots like Calvert Cliffs and Solomon's Island the Hollow makes for the perfect vacation destination. Enjoy sunrise views through the treetops each morning on the expansive back deck, or use our eco-friendly wood burning stove for autumn and winter nights. Unlike many beach houses, this home is surrounded by trees making it serene. UPDATED PHOTOS SOON

Pets · Walkability · Air conditioning

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Waterfront oasis on Nomini Creek with over 380 feet of waterfront nestled on a 2.6-acre lot and only 2hr from DC, 1hr from Richmond. This home has been fully updated and offers plenty of space for your family or friend retreat. a dream kitchen, huge open concept 2 story living room with incredible floor to ceiling windows offering incredible views of the water and a fireplace. Nice patio with firepit offers incredible views. Bring your boat or Jetski to the dock. This property is amazing.

Outdoor spaces · Pets · Long stay

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Walkability · Outdoor spaces · Bathroom

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

Pets · Outdoor spaces · Pool

Waterfront on St. Leonard Creek at Fort Hill

Waterfront home on St. Leonard Creek w/ private pier for fishing and relaxing, PLUS a small beach area. Close to Solomons, fossil hunting at Calvert Cliffs, the Calvert Marine Museum (and their concerts), and other area attractions. Forget stairs! Our elevator directly connects the parking area to your private floor! Fort Hill is a uniquely quiet and private space with wide-open views of the outdoors. 4 kayaks are included FREE for you to enjoy!

Walkability · Outdoor spaces · Bathroom

Potomac River Getaway

Discover an incredible escape at our cliffside gem on the Potomac! This 3BR, 2.5BA retreat has airy living spaces and panoramic river vistas from the wraparound deck. Enjoy your coffee as eagles soar above, and unwind in a private hot tub beneath star-filled skies, all while soaking in breathtaking riverside sunsets. Perfect for family and friend getaways, with historical sites close by. Montross’s small-town charm awaits your exploration—enjoy!

Outdoor spaces · Pets · Parks

Cozy Waterfront Cottage - Pet Friendly

Original waterfront cottage in North Beach is perfect for a small family or two couples. Beautiful sunrises and moonrises over the boardwalk from the front deck. Walk to restaurants and nightlife, stroll the boardwalk, chill on the beach or go to the spa or charter fishing in Chesapeake Beach. Pet friendly. Beach Passes, umbrella and chairs included. 2 bedrooms plus a twin daybed that pulls out to queen bed.

Pets · Walkability · Hospitality

The Little Gypsy BoHome

Escape to a private Chesapeake Bay retreat with stunning water views and sunsets. Located in peaceful Tracy’s Landing, this coastal home offers relaxed charm and resort-style amenities. Enjoy a saltwater pool, private beach, sauna, steam shower, canoe, and outdoor spaces. Perfect for families, couples, or friends, with easy access to Annapolis and D.C. Relax, recharge, and make unforgettable memories.

Pets · Outdoor spaces · Amenities