Family-friendly vacation rentals in St. Mary's County

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 --

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

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!

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your newly renovated 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 available for rent.

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Relaxing Beach Getaway Loft Apartment

Note: We are a peanut-free property. Read our reviews! RELAX in our chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a five minute drive away. Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please!

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

Waterfront Cottage on the Potomac River

Escape to our serene waterfront cottage on the Potomac River, just 2 hours from Washington D. C. and the Richmond area. This retreat comfortably sleeps 5 and features a private pier for fishing, a sandy beach for relaxing, cozy sun room for reading, and breathtaking water views. Enjoy a fully stocked kitchen, fast WiFi, and a spacious deck. The perfect spot for a romantic weekend, a special celebration or a simple peaceful retreat.

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).