Pet-friendly holiday rentals in Southern Maryland

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

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 --

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Rest & Recharge, A-frame Cabin on Winery Grounds

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Waterfront Cottage in Colonial Beach at Placid Bay

Luxury Cottage with private water views full of natural wildlife. You will love the open floor plan with a chef's kitchen stocked with All the essentials including beverages and coffee. Sleep late with private bedrooms that include luxurious bedding Enjoy the expansive outdoor space complete with Patio, Pergola, Fire Pit, and large deck with outdoor kitchen. Walk down to the 28ft foot dock where you can fish, relax in the sun or take the Kayaks for a ride Close to DC and NOVA

Island Shanty

Cozy custom built houseboats on charming Solomons Island. Walking distance to restaurants, live music, boardwalk and unique shops. In the morning, have your coffee on the deck overlooking the harbor and watch the sailboats going by. In the evening enjoy a glass of wine on the deck while you listen to good bands on the weekends at the famous Tiki Bar. One SMALL well behaved pet ( no barkers please) is allowed and must be approved by owner $100 non- refundable pet fee.

Quiet Luxury Home - Modern - King - 20 Min from DC

Completely new renovations with an eye for details have created a space that feels like a custom built home. Made to provide you with a memorable luxury rental experience. Comfortable, bright, modern, unique and stylishly furnished mastering the mix of timeless elegance and modern simplicity. An open floor plan space that’s equally welcoming and sophisticated, incorporating natural elements, layered fabrics, and textures.

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, a basketball hoop, beach access, a canoe, a gas grill, a steam shower, and an outdoor redwood infrared barrel sauna.

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Bikes are available and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Waterfront Escape w/ Private Dock & Fire Pit

Escape to Mallard Cottage, our renovated home nestled along the picturesque Nomini Creek. Step onto the private dock for direct water access, where you can launch one of our paddleboards or kayaks for a day of exploration. Highlights include: ✔ 4 Outdoor Decks ✔ High-Speed Wi-Fi ✔ Central Heating & Air Conditioning ✔ Game Room ✔ Free Parking ✔ No Cleaning Fee!

Waterfront FamilyFriendly Home Improved for 2023

NEW IMPROVEMENTS for. 2023! Nautically furnished home on the water and a cul-de-sac which offers a relaxing and safe getaway space for guests. Large windows along the waterside provide for views from most rooms in the house. Watch the boats come and go from Smith Point Marina, or charter a boat for cruising or fishing.