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Chesapeake Escape

Come stay with us at Chesapeake Escape in Prince Frederick, MD. Stylish Chesapeake retreat just one block from the Bay! Enjoy fossil hunting, hiking, sunrise views, and take day trips to DC or Annapolis. Launch jet skis or kayaks from the nearby community ramp, and enjoy seasonal crabbing, fishing, and hunting. Newly renovated with a peaceful, modern design, it’s ideal for couples, small or large groups, families, or solo travelers. Settle in with fast Wi-Fi, smart TV—your coastal escape awaits!

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!

Warm Home Overlooking the Chesapeake Bay

Sitting on the Chesapeake Bay, North Beach is a town where you are so close to things, yet can feel so far away. Only 45 minutes form Washington, DC, you can sit on one of three decks and gaze into the Chesapeake Bay, enjoying all that small town life has to offer. An open plan, with defined spaces, the house is at once cozy (with a fireplace) and spacious for a family. It is great for couples, adventurers, business travelers, and families. This is not a house for large groups or parties.

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.

Osprey's Perch

Welcome to Osprey’s Perch! A kid & dog friendly house with 3 bedrooms, 2 full bathrooms, large driveway, firepit, grill, & a fully fenced-in backyard. It's an easy 5 block walk to the beach & during your stay you can borrow our beach pass. Featuring high-speed Wi-Fi, a large, dedicated workspace, & streaming services available on the TV. This family-friendly rental offers the perfect backdrop for cherished moments & relaxation. Best of all, you don't have to clean at check out!

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

Cottage on the Creek

The Cottage is perfectly perched alongside Cuckold Creek showcasing the beauty of Southern Maryland. Our home provides plenty of space for relaxing together with a water view everywhere you turn. Each space is set up to provide you with the comforts of home, so you can relax and enjoy being in the moment. Located in the heart of Hollywood, not too far from stores or restaurants, but still "away from it all". ✨

Charming Stay Near the Bay- w/Beach Passes!

Relax in this charming pet friendly 3BR, 2BA North Beach retreat- perfect for families, couples, and small groups. Walk to the beach, local restaurants and shops. FREE beach passes up to 5 guests included!. Enjoy a fully fenced yard, full kitchen, on site washer/dryer, and fast WIFI. We provide all linens, beach chairs, an umbrella, and beach towels making it easy for you to pack light and enjoy your vacation.

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.

Full house rental in Twin Beach. 1 bk from the Bay

A block from the Chesapeake Bay and North Beach boardwalk, this charming beach cottage is the perfect place for a weekend away by the water but still close to the activities of the DMV. Great location for groups who have booked fishing excursions on the bay or families in town for a wedding celebration. During the week, enjoy easy access to commuter busses to DC, with pickup only steps away.