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

Modern River Relaxation

Welcome to your modern retreat at Colonial Beach. Newly built with sleek design, this single home is perfect for families and friends seeking both relaxation and adventure. Located just a short walk or lively golf cart ride to the beach, this home places you close to the best local dining, breweries, wineries, and attractions. Private hot tub for relaxing, and a huge outdoor screened living space to maximize fun. Community pool open thru mid-Oct and playground just steps away! Pet friendly!

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.

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

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!

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

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.

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

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