Farmstay holiday rentals in Southern Maryland

Peaceful Family-Friendly Retreat Near DC · Pets OK

Tucked away in a peaceful, wooded setting near DC, this apartment with a private entrance features a bright, airy layout designed for comfort. Living/dining/kitchen with fireplace, 65” TV, books & games, fully stocked kitchen, and workout gear. King bedroom with famously comfy memory foam mattress, second bedroom with twin daybed + pop-up trundle, full bath with shower/tub combo, gigabit Wi-Fi, desks, porch + grill. 10 min to Metro, 20 min to DC, and 5 min to Greenspring Senior Living Community.

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

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

Welcome to the Butterfly Effect! Recharge at this tranquil getaway. 2.5 wooded acres with a private dock and cove, a short paddle away from the lake beach with a swimming dock and sandy beach! Fishing, swimming, and floating all on the protected freshwater lake. We have boats for your use, theater space & hot tub to wind down at night after dining on our deck. Picnic at our private Shark Tooth Beach, watch Osprey & Eagles fish the Potomac, and collect 15-million-year-old fossilized shark teeth!

The Rosé Retreat: Pool-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Cabin Sweet Cabin

Relax with the whole family at this peaceful rustic resort getaway! D.C., Richmond, Lake Anna, Colonial Beach, Fredericksburg battlefields, Kings Dominion, and the Raceway are all just a short drive away for vacationing fun! OR stay & play at the cabin with the hot tub, walking trails, firepit, outdoor games, bumper pool, arcade games, connect 4 hoops, theater room, and lots of places to relax! Boat & RV parking available. A little bug spray recommended. Other amenities are available (ask us!).

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

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.

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

Horse farm near Manassas Battlefield.

“Chip and Joanna” style accommodations. Private suite, private entrance (bedroom, bath, kitchenette). Close to: Manassas Battlefield (25 mile trail); Skymeadow State Park (nice trails); Wineries, distilleries, breweries and great restaurants -5 miles; VRE connections - to METRO; 3 miles to Manassas airport. ONLY 6 miles to Jiffy Lube Live. Fire pit and wood. Not accepting pets at this time. Cot and Pack n Play available.

Sandy House - Relaxation on the Potomac River

Whether you want to get away from the stress of the city or you are looking for a place to enjoy some of the most beautiful outdoor scenery in Southern Maryland, the Sandy House at Budds Ferry Farm has it all. A hidden gem, the Sandy House is a perfect venue for hunters, fishermen, nature lovers and photographers. This home has the comfort of modern amenities in a beautiful country setting.

The Civil War House

The Civil War House, circa 1860's, offers both wood-burning and gas fireplaces, FULL-kitchen, private patio, and second bedroom, loft bedroom AND sofa bed, this 1800 ft² antique home is befitting for a couple, small family or extended stay. Max occupancy of 5 guests. Pets are allowed and are charged a fee of $25 (first night) and $15 (per ea. add'l night).

1840's Cottage: 3 miles from I-95/ Near Shopping

Welcome to Bunker Hill Farm est 1840 My quaint building is 538sq ft. It used to be the old detached kitchen situated behind my farmhouse from the 1840s. This historic building was converted into a guest house. Full Kitchen and Dinnete. Bath and Bedroom with Closet. This building is on an animal farm with goats, ducks , chickens, and a Miniature Donkey.