
Family-friendly holiday rentals in St. Mary's County
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Top-rated family-friendly rentals in St. Mary's County
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Our Little Piece of Heaven
Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

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.

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.

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

White Point Cottage -- Quiet Waterfront Getaway
Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Little House by the water
Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Serenity Suite on Chesapeake Bay
Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

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!

Fleets Cove Farm *PETS STAY FREE*
Welcome to Fleets Cove Farm y'all! Looking for a peaceful and secluded place to stay? We have the place for you! With expansive fields surrounded by tall hardwood trees, it's hard not to love the light breeze and quiet. At night, sitting around the fire pit and looking at the stars is a must. The mini donkeys and cows are always looking for new friends. We also have seasonal animals like pigs, chickens, and ducks at different times of the year.

Cozy Little Cottage
The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

Waterfront Cottage on the Potomac River
Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.
Popular amenities for St. Mary's County family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Peace Point - Waterfront, Secluded, Home w/hot tub

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Riverside Haven w/ Hot Tub

Waterfront 4-BR home w/ hot tub & charging station

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Cozy & Content River Retreat Beach Hot Tub & Games

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Family- and pet-friendly home rentals

2 Bedroom Cozy Beach Cottage

The River House, a Wicomico Beach Retreat

Charming Waterfront Home with Expansive Views

Peaceful Waterfront Retreat on The Bay

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Winter Waterfront Escape: Dock, Views, & Fire Pit

Cove Point Cottage with Chesapeake Bay views

Perfect spot for a Vacay!
Family-friendly home rentals with a pool

3N+ PROMO Waterfront w/Gameroom, Dogs + EV OK

Waterfront Paradise with a Private Pool

New Private Beachfront panoramic view every window

The Glebe

Shewell’s Basement Studio at Long Beach

Harbor Cottage

Beach Please! River cottage w/private beach & dock

Waterfront, pier, hot tub, pool, pizza oven
Destinations to explore
- Rentals with a washing machine and dryer St. Mary's County
- Beachfront rentals St. Mary's County
- Rentals with a fire pit St. Mary's County
- Rentals with breakfast St. Mary's County
- Rentals with pools St. Mary's County
- Apartment rentals St. Mary's County
- Rentals with lake access St. Mary's County
- Cottage rentals St. Mary's County
- Rentals with a fireplace St. Mary's County
- Rentals with a kayak St. Mary's County
- Waterfront rentals St. Mary's County
- Pet-friendly rentals St. Mary's County
- House rentals St. Mary's County
- Rentals with outdoor seating St. Mary's County
- Rentals with a patio St. Mary's County
- Rentals with beach access St. Mary's County
- Rentals with a hot tub St. Mary's County
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Chesapeake Bay
- Haven Beach
- Bethel Beach
- Piney Point Beach
- North Beach Boardwalk/Beach
- Ragged Point Beach
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Bayfront Beach
- Sandyland Beach
- Rose Haven Memorial Park
- Oxford Beach
- Guard Shore
- Gerry Boyle Park
- Franklin Manor Community Private Park
- St George Island Beach
- Brownies Beach
- Marshalls Beach
- Cordreys Beach
- Langford Sand
- Lane Beach
- Layton's Chance Vineyard and Winery
- Ingleside Vineyards
- Bordeleau Vineyards & Winery




