
Family-friendly vacation rentals in St. Mary's County
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Top-rated family-friendly rentals in St. Mary's County
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Wits End Retreat-Relaxing Beautiful 3 Bedroom home
Leave your cares behind when you stay at Wits End. Relax with the whole family, take a couples getaway or stay long term at this peaceful property. This 1800 sq. ft. 3 bedroom 2 bathroom rancher style home has the comfort of modern amenities in a beautiful rural country-like setting. It's steps away from a community park, minutes away from several bodies of water including the Chesapeake Bay and a short drive to the Point Lookout State Park, St. Mary's College of MD and Patuxent Naval Air Base.
FamilyIndoor spacesBathroom
4.95 out of 5 average rating, 132 reviews
Waterfront with sweeping bay view & private beach
Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.
FamilyIndoor spacesBeach
4.97 out of 5 average rating, 114 reviews
Retreat at Fenwick
This cozy one bedroom apartment is the perfect place to unwind & relax. Located in the heart of downtown Leonardtown, the Retreat at Fenwick is steps away from many delicious dining opportunities, unique and fun shopping at local boutiques, and entertainment experiences. It includes free wifi, a full kitchen & complimentary coffee bar, a charming eat-in dining space, queen size bed, full size pull out sofa bed, a cozy electric fireplace, workspace, and twin bunkbeds that are great for kids!
FamilyKitchenAccuracy
4.96 out of 5 average rating, 113 reviews
Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!
Now offering 2-night stays!! Send a msg to ask about this! Just added-Hot Tub! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. We've just put in a hot tub!!! Photos will be taken when it stops raining. Six bedrooms and 5 full baths. Lots to do with an outdoor pool, an nicely equipped recreation room, and a dock from which to launch your kayak or canoe. Easy access to plenty of activities in the surrounding area makes for a memorable vacation.
Indoor spacesKitchenCheck-in
4.93 out of 5 average rating, 107 reviews
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.
FamilyKitchenLayout
4.96 out of 5 average rating, 276 reviews
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.
KitchenIndoor spacesTV
4.97 out of 5 average rating, 626 reviews
Pizza Friday
Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet waterfront oasis boasts four-bedroom and two-full baths with large picture windows offering panoramic water views from almost every room. The large updated kitchen features stainless appliances, ample cabinetry, granite countertops, and a breakfast nook. There is a large sunny dock, a pizza oven, kayaks and a canoe to enjoy the water. If you're looking for the perfect weekend getaway, this is it!
FamilyIndoor spacesParking
4.93 out of 5 average rating, 104 reviews
Its always a good day by the water!
Enjoy our private Loft apartment with exclusive beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance, so come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach-- just a 5 minute drive away. Please let us know if you plan to use it!
KitchenIndoor spacesOutdoor spaces
5.0 out of 5 average rating, 427 reviews
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.
KitchenIndoor spacesTV
4.96 out of 5 average rating, 191 reviews
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.
Indoor spacesFamilyLong stay
4.86 out of 5 average rating, 170 reviews
Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).
KitchenIndoor spacesAccess
4.99 out of 5 average rating, 179 reviews
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage
KitchenFamilyLong stay
4.97 out of 5 average rating, 137 reviewsPopular amenities for St. Mary's County family-friendly rentals
Family-friendly home rentals with a hot tub

Hot Tub Hideaway by Shark Tooth Shores
Indoor spacesFamilyAmenities
4.85 out of 5 average rating, 101 reviews
Peace Point - Waterfront, Secluded, Home w/hot tub
FamilyKitchenAccuracy
4.99 out of 5 average rating, 142 reviews
Waterfront 4-BR home w/ hot tub & charging station
KitchenIndoor spacesCondition
4.99 out of 5 average rating, 142 reviews
Waterfront Cottage w Water Access, Sauna, Hot Tub
Indoor spacesKitchenTV
4.93 out of 5 average rating, 150 reviews
Blue Pearl-Luxury estate with private dock/jacuzzi
KitchenIndoor spacesBathroom
4.97 out of 5 average rating, 107 reviews
Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC
FamilyIndoor spacesQuiet
4.94 out of 5 average rating, 200 reviews
Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach
KitchenFamilyQuiet
4.93 out of 5 average rating, 130 reviews
Bayfront Walk-Out Beach Home | Sunrise & Fire Pit
KitchenIndoor spacesLocation
4.99 out of 5 average rating, 113 reviewsFamily- and pet-friendly home rentals

The River House: A private waterfront oasis…
Indoor spacesFamilyAccess
4.94 out of 5 average rating, 100 reviews
Old World Cottage/Fabulous Sunsets/Polite Pets OK
KitchenFamilyGrill
4.89 out of 5 average rating, 133 reviews
Waterfront home, private dock
FamilyKitchenCheck-in
4.97 out of 5 average rating, 111 reviews
Hideaway on the Bay: Waterfront Vintage A Frame
FamilyKitchenBathroom
4.91 out of 5 average rating, 269 reviews
Cove Point Cottage with Chesapeake Bay views
KitchenFamilyView
4.98 out of 5 average rating, 261 reviews
Peaceful Waterfront Retreat on The Bay
FamilyKitchenWalkability
4.89 out of 5 average rating, 323 reviews
Spacious Lake House at the Chesapeake Bay
KitchenIndoor spacesCleanliness
4.92 out of 5 average rating, 107 reviews
The River House, a Wicomico Beach Retreat
KitchenIndoor spacesPets
4.91 out of 5 average rating, 129 reviewsFamily-friendly home rentals with a pool

Waterfront, 3 Beaches, Dock+Kayak, Potomac, Dog OK
FamilyIndoor spacesGrill
4.98 out of 5 average rating, 161 reviews
Coastal Waterfront Escape Fire Pit, Dock & Kayaks
Indoor spacesKitchenPets
4.96 out of 5 average rating, 107 reviews
The Glebe
KitchenIndoor spacesAmenities
4.92 out of 5 average rating, 234 reviews
Beach Retreat
KitchenFamilyCheckout
4.85 out of 5 average rating, 127 reviews
Granary Apartment in Kinsale
Indoor spacesKitchenCheck-in
4.89 out of 5 average rating, 111 reviews
Studio on the Bay.
Indoor spacesFamilyAccuracy
4.97 out of 5 average rating, 126 reviews
Bell House
Indoor spacesKitchenLocation
4.97 out of 5 average rating, 31 reviews
Waterfront, pier, hot tub, pool, pizza oven
KitchenIndoor spacesQuiet
4.98 out of 5 average rating, 43 reviewsDestinations to explore
- Beachfront rentals St. Mary's County
- Rentals with a hot tub St. Mary's County
- Apartment rentals St. Mary's County
- Guesthouse rentals St. Mary's County
- Pet-friendly rentals St. Mary's County
- Cottage rentals St. Mary's County
- Rentals with beach access St. Mary's County
- Rentals with a kayak St. Mary's County
- Waterfront rentals St. Mary's County
- House rentals St. Mary's County
- Rentals with pools St. Mary's County
- Rentals with lake access St. Mary's County
- Family-friendly rentals Maryland
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