House vacation rentals in Hollywood, St. Mary's County

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million+ old shark teeth, and a fossil cliff beach. Fishing! Hot tub on the patio! Bald eagle sightings! Theater Room!

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Greystone Manor-Magnificently restored! Sleeps 10

Enjoy this magnificently renovated home in the center of town in Colonial Beach. Every inch of this house has been renovated and re-styled with a mix of the past and present. This home boasts 3 large bedrooms (1 King bed with ensuite, 2 Queen beds) and a large loft with 4 twin beds that would make every tweenager delighted! Each bedroom and living space has smart-TV's, and there is plenty of room to entertain and enjoy the outdoor spaces.

Chesapeake Bay Waterfront View

Indulge in your dream vacation at our one-of-a-kind bay house! This three-level home offers unmatched water views that will captivate you. Strategically located 15 min away from Solomons Island, for a city escape, with exclusive access to 2 private sand beaches and a lake. Our home is a delight, a blend of comfort, fun and tranquility. Highlights: Breathtaking Water Views Gourmet Kitchen Screened Deck Private beaches