Mansion holiday rentals in Maryland

Harrison House - in Town and on St Michaels Harbor

The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels, rented as such since 1992. It is the only large (6 bdrm) vacation rental in Town. The house is located on the harbor (spectacular water views) and the town park in the center of St. Michaels - walking distance to all museums, parks, shops, stores, restaurants, town pool, tennis courts and library. Rates vary by day of the week and season. Discounts for week stays or "last minute" bookings.

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Amazing Views! | 4BD/4.5BA | Dock, WISP, Hot Tub

Get away from it all! Our home features four large bedroom suites, two spacious family rooms, elevated deck lake views, and a boat slip. And pets are welcome! Nestled on a wooded hillside, you will love the feeling of seclusion while still being central to all DCL activities. We offer a new kitchen and comfortable home furnishings that invite you to unwind. Gather around the fireplace, relax in the hot tub, get on the lake, or step outside onto the deck, and enjoy that fresh mountain air!

Luxury OC Beach House w/ Deluxe Game Room & Pool!

Escape to paradise in downtown OC’s exclusive Mallard Island with this exquisite, large 4-bedroom, 4-bath beach house nestled on a huge lot! Specifically for families, this amazing home boasts a plethora of amenities, including a gameroom with pinball machines, shuffleboard, arcade, & wet bar. The backyard oasis with in-ground pool is primed for entertainment. Linens included in cleaning fee! Experience the ultimate coastal getaway where relaxation & recreation intertwine seamlessly.

Waterfront Estate with Pool on 16 acres

Looking for a place to enjoy a water front estate on 16 acres of land? Look no further than Cherry Grove Manor. It is a traditional style home that sleeps 18 & features 6,000 sq. ft. on 3 levels of living. Enjoy your private 550 ft. sandy beach that overlooks the mouth of the Elk River with views into the Chesapeake Bay. There is a private dock that you can fish and crab from. The newly renovated Salt Water Pool (not heated) offers views of the water. (Pool available May-September. )

Renovated Home with Dock, HotTub, Golf DogFriendly

Recently renovated, this beautiful home sits on a hillside in the Waterfront Greens community. Stunning views, privacy, great location, and many amenities make it the perfect choice. The new deck has plenty of seating & some of the best views around. Waterfront Greens offers a par 3 golf course, mini golf, tennis, lake access and the dock area. One of the best locations in the area for safely walking & riding bikes. Please note that there is a pet fee (for up to 2 dogs) of $200.

Luxury Home, Sleeps 15, Private Pool, Close to DC

Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views and private salt water pool, perfect for that special gathering. Secluded yet just 35 minutes from Capitol Hill and 20 minutes from Annapolis. The home, with its high ceilings, huge windows and expansive decks comprises over 8000 square feet, so there is plenty of room to stretch out. *** IMPORTANT Please send AN INQUIRY with a little about you PRIOR to requesting a booking.

Winter Sale! Near Wisp! Hot tub! Fire Pit!

*Within walking distance to the lake! *Pool Table, darts, multipurpose game table, board games, cards. *spacious kitchen & great room *Plenty of parking *Lake access from the neighborhood dock are extra perks!*cozy beds *large deck *Hot Tub *huge dining table *make s'mores at the firepit *walk around the quiet neighborhood *Relax/watch the wildlife walk through yard. *TVs in every room provide entertainment for all!

No Fees~Historic Lansdowne Manor

Welcome to Lansdowne Manor, some of the best preserved history of the late 18th/early 19th century on the Eastern Shore. Partially restored and tastefully amended, this historic home is superbly utilitarian. The grand double parlors can be used for small dinner parties or quiet Netflix nights. Situated on 19 acres, enjoy unmatched privacy and tranquility. Sleeps up to 8.