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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 --

Patuxent River View

🏡Stay at this peaceful, amenity‑rich guest house near North Beach, Chesapeake Beach, and Herrington Harbour, with quick access to Washington, DC, Baltimore, and Annapolis. Enjoy a fully stocked kitchen, coffee, fast WiFi, a seasonal pool, and a shaded gazebo designed for comfort and convenience. Perfect for wedding weekends, family visits, work trips, and quiet coastal getaways, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring the area.

Spacious Beach House Top Floors - Walk Everywhere!

This booking is for the entire SECOND story & loft of a DUPLEX-style beach house. Entrance, access, & all indoor spaces of the unit are private, however there are often other guests and families on the first floor. There is also a STAIRCASE to the 2nd floor unit and a STAIRCASE to the loft. Please ensure this home suits your needs. The space has an open floor design with 14' cathedral ceilings for a spacious modern feel with beach-house charm. Walk 2 blocks to the beach, boardwalk, and more!

Rising Sun Cottage 3Bed 3 bathroom W/ Beach Views!

Welcome to this stunning Chesapeake Bay waterfront home. This spacious, three-level home offers the perfect vacation retreat with breathtaking views of the Bay from nearly every room. Step through the front door, and be greeted by panoramic water views The spacious kitchen and the large screened porch are perfect for enjoying a nice meal or sipping coffee while watching the sunrise over the water. Upstairs, the wood spiral staircase leads to a lovely great room with expansive views of the Bay,

Charming Historic 2 Bedrooms on the Chesapeake Bay

Come visit North Beach, Maryland! Enjoy year-round activities, crab houses, and great restaurants. Our quaint 100-year-old cottage sits directly on the Chesapeake Bay. Relax on the front porch and watch the sunrise. Take a short walk to the charming shops and eateries. The comfortable cottage has everything you need for a getaway. Just a stone’s throw away from the half-mile-long boardwalk and bike trails. Stroll to the Saturday morning Farmer’s Market, First Fridays, and movies on the beach!

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

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 dates**

Luxury Farmette -Private & Secluded-1hr to DC

Plan your tranquil getaway to the countryside and escape to a luxury dream farmhouse. Located on 5 acres, the renovated home offers peace in a quiet, private location. Guests have access to a pool and outdoor shower, fire pit, a covered grilling area and a playground for children. The home is located approximately 1hr from Washington DC and is the perfect place for a retreat, family vacation and everything in between! Plenty of parking available for those traveling with boat/camper/RV.

Relaxing retreat on the river.

This river retreat is located in Owings, MD This Guesthouse is located on the Patuxent River and is surrounded by beautiful nature. Get up in the morning and enjoy your coffee watching the Osprey, Eagles, and Hawks fish for their morning breakfast. Located about 40 minutes away from Annapolis and DC for easy day trips. Come back in the evening and grill outside watching the beautiful sunsets. Your host lives in a historic home on the same property dating back to the early 1800's.

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

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”).

Cozy Waterfront Cottage - Pet Friendly

Original waterfront cottage in North Beach is perfect for a small family or two couples. Beautiful sunrises and moonrises over the boardwalk from the front deck. Walk to restaurants and nightlife, stroll the boardwalk, chill on the beach or go to the spa or charter fishing in Chesapeake Beach. Pet friendly. Beach Passes, umbrella and chairs included. 2 bedrooms plus a twin daybed that pulls out to queen bed.