Farm Stay in Maryland
10 guests · 5 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this farm stay rental
SHADY OAK FARM – PRIVATE LUXURY RETREAT & YEAR-ROUND RESORT-STYLE STAY
Shady Oak Farm is a 32-acre private estate designed for guests seeking space, comfort and a resort-style experience in a peaceful, secluded setting. This luxury vacation rental offers a unique blend of privacy, recreation and elevated amenities, making it ideal for families, groups and multi-generational stays.
The home features five spacious bedrooms, six bathrooms, large TVs in every bedroom and multiple indoor and outdoor gathering areas. The layout comfortably accommodates groups while still providing private spaces to relax and unwind.
SUMMER SEASON
Heated pool open May 1 through September 30
During the warmer months, guests have access to the heated saltwater pool, multiple outdoor seating areas and a cedar-finished pool house equipped with a bathroom, refrigerator, screened porch and 65-inch TV. The outdoor space is designed for extended stays, relaxation and group enjoyment.
A 7-person hot tub is also available year-round for additional comfort and relaxation.
HOLIDAY SEASON
Holiday décor displayed November 1 through January 31
During this period, the property is fully decorated with seasonal trees, festive décor and thousands of sparkling lights throughout inside and outside of the estate. Guests can enjoy the hot tub, fire pit, karaoke lounge and private theater in a fully prepared holiday setting.
All seasonal decorating is completed before arrival, allowing guests to simply enjoy the atmosphere without any setup required.
YEAR-ROUND AMENITIES
Indoor features include a karaoke lounge with JBL speakers and microphones, multiple TVs, an 85-inch theater screen with Bose surround sound, a Velodyne subwoofer, reclining leather seating, a game room with ping pong and poker, a custom bar and a fully equipped kitchen designed for group use.
Outdoor amenities include a year-round hot tub, fire pit with supplied firewood, swing set, cornhole, picnic areas, open grassy spaces, walking trails and a private fishing pond. Additional family-friendly items such as toys, board games, a high chair and a Pack ’n Play.
NEARBY ATTRACTIONS
• 5 min – Pavilion at Weatherly Waterfront
• 10 min – Cobb Island waterfront dining
• 10 min – La Plata shops and restaurants
• 10 min – Swan Point Yacht & Country Club
• 15 min – Budds Creek International Raceway
• 20 min – Colonial Beach fishing pier and dining
• 20 min – Wicomico Shores Golf Course
• 25 min – Historic Leonardtown
• 45 min – Solomons Island
• 45 min – MGM National Harbor Resort & Casino
• 1 hr – Washington, D.C.
• 1 hr – Kings Dominion amusement park
Shady Oak Farm offers a private, resort-style setting designed for comfort, connection and extended stays in every season.
Shady Oak Farm is a 32-acre private estate designed for guests seeking space, comfort and a resort-style experience in a peaceful, secluded setting. This luxury vacation rental offers a unique blend of privacy, recreation and elevated amenities, making it ideal for families, groups and multi-generational stays.
The home features five spacious bedrooms, six bathrooms, large TVs in every bedroom and multiple indoor and outdoor gathering areas. The layout comfortably accommodates groups while still providing private spaces to relax and unwind.
SUMMER SEASON
Heated pool open May 1 through September 30
During the warmer months, guests have access to the heated saltwater pool, multiple outdoor seating areas and a cedar-finished pool house equipped with a bathroom, refrigerator, screened porch and 65-inch TV. The outdoor space is designed for extended stays, relaxation and group enjoyment.
A 7-person hot tub is also available year-round for additional comfort and relaxation.
HOLIDAY SEASON
Holiday décor displayed November 1 through January 31
During this period, the property is fully decorated with seasonal trees, festive décor and thousands of sparkling lights throughout inside and outside of the estate. Guests can enjoy the hot tub, fire pit, karaoke lounge and private theater in a fully prepared holiday setting.
All seasonal decorating is completed before arrival, allowing guests to simply enjoy the atmosphere without any setup required.
YEAR-ROUND AMENITIES
Indoor features include a karaoke lounge with JBL speakers and microphones, multiple TVs, an 85-inch theater screen with Bose surround sound, a Velodyne subwoofer, reclining leather seating, a game room with ping pong and poker, a custom bar and a fully equipped kitchen designed for group use.
Outdoor amenities include a year-round hot tub, fire pit with supplied firewood, swing set, cornhole, picnic areas, open grassy spaces, walking trails and a private fishing pond. Additional family-friendly items such as toys, board games, a high chair and a Pack ’n Play.
NEARBY ATTRACTIONS
• 5 min – Pavilion at Weatherly Waterfront
• 10 min – Cobb Island waterfront dining
• 10 min – La Plata shops and restaurants
• 10 min – Swan Point Yacht & Country Club
• 15 min – Budds Creek International Raceway
• 20 min – Colonial Beach fishing pier and dining
• 20 min – Wicomico Shores Golf Course
• 25 min – Historic Leonardtown
• 45 min – Solomons Island
• 45 min – MGM National Harbor Resort & Casino
• 1 hr – Washington, D.C.
• 1 hr – Kings Dominion amusement park
Shady Oak Farm offers a private, resort-style setting designed for comfort, connection and extended stays in every season.
Amenities at Secluded 32 Acre Retreat, Pool, Hot Tub, Karaoke, Theater, Gm Rm, & Fire Pit Fun
Non-smoking
No pets allowed
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Oct 2025
The house has everything you need for a comfortable stay with friends and family.
10 / 10Outstanding·Oct 2025
This home was amazing…from the front door to the back yard. Perfect place for our family to spend time together for a special weekend.
10 / 10Outstanding·Aug 2025
The home was immaculate and beautifully decorated! Everything that is in the listing is accurate and even better than we expected. Our host, Kim, was exceptionally helpful from the time of booking and during our stay. Everything was well stocked and the large rooms made it so we never felt crowded and had plenty of space to gather for family activities. Cannot say how wonderful our trip was and made many new and happy memories….absolutely 5 stars!! Thank you, Kim!!
10 / 10Outstanding·Aug 2025
We had a spectacular stay with 3 generations of my family. The property was beautiful and quiet and the pool exceeded our expectations. We were lucky enough to see a bald eagle fly by us in the pool. What a treat! The kitchen was well equipped as was the entire house. Kim communicated quickly and was extremely responsive. We have stayed in many VRBO rentals over the years, but this one ticked all the boxes and we hope we can make it back there again. One thing to note is that each bedroom has only 1 bed, so it did cause some discussion amoung my teens but that being said, the beds were very comfortable!! Thanks again Kim
$$$$
Top rated by guests
10Outstanding
(16 Ratings)
"The house has everything you need for a comfortable stay with friends and family."
Mary M.Don't miss out! Price and availability may change
