Holiday houses in Benedict

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Downs By The River

Welcome to Downs at the River: Your Tranquil Waterfront Escape Are you dreaming of a peaceful getaway where nature’s beauty surrounds you? Look no further than Downs at the River! Nestled along the serene banks of the Patuxent River, this stunningly renovated home is your ideal retreat. With breathtaking views and modern comforts, this space invites you to unwind, explore, and reconnect with what matters most. Endless Water Adventures Await

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).