Farmstay holiday rentals in Southern Maryland

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!

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!).

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

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!

Irvington Cottage - Vineyard Birdhouse

Beautiful & peaceful 3 bedroom (1 King, 1 Queen, Twin Beds), 3 bath cottage with screened porch nestled in the woods in a quiet neighborhood with nature trails and dock. Perfect getaway for adults/family. Walk or bike to the charming town of Irvington. Explore the shops and restaurants in the area. Enjoy sunset dinner at nearby river restaurants; eat oysters! Close to Tides Inn. Premium Cable TV, high -speed WIFI for your convenience. Note: NO PETS, no smoking, no parties allowed.

Charming Cottage On Horse Farm Middleburg Area

The cottage is set on a beautiful private farm in the center of historic Aldie, Va. and 5 minutes to historic Middleburg. The cottage is surrounded by 11.11 privately fenced acres and is in a very cute setting with a shower and bathroom downstairs along with a kitchen and bedroom upstairs with one queen bed. The apartment accommodates 2 easily with table and chairs inside and on the porch for your comfort. Great opportunity to experience and relax on a small farm in hunt country.

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

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.

Modern Farm Stay

Enjoy a peaceful farm retreat in this cozy studio, convenient to local wineries, farm markets, the Flying Circus, and Shenandoah National Park. We’re also close to top wedding venues like Great Marsh Estate, Morais, and Poplar Springs - perfect for event guests or a quiet country getaway.