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Breathtaking Waterfront Now booking Fall 2025

Booking Fall 2025/ Summer 2026 The incredible 4-bed 2-bath water-facing home is the ultimate getaway. Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with a $125 docking fee), jet ski and fishing gear. Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2), or simply relax on the peaceful deck that spans the back of the home. May-September is when the private saltwater pool and jacuzzi are open. Closed Oct- mid May

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

3900 Ft to the Water | Smart Home | Multiple Living Spaces | Fire Pit Adventure beckons in the Chesapeake Bay — let this 3-bed, 2-bath North East vacation rental be your home base for shopping, dining, boating, and more! After exploring the area's beaches and hiking spots, return to the house and soak in the spa under the stars or enjoy a meal fresh off the smoker. Ready to turn in? Enjoy a nightcap in the basement bar. The East Coast lifestyle is yours to embrace at this Maryland getaway!

Historic Victorian Queen Chesapeake City

Welcome to your perfect getaway! This beautifully renovated and professionally decorated 5-bedroom, 4-bathroom home combines modern luxury with classic charm — all just steps from town. Enjoy the gourmet kitchen. Outside, unwind by the private in-ground pool, soak in the hot tub, or sip your morning coffee on the screened-in porch. Located in-town and walking distance to shops, restaurants, local boat docks, and fun. You’ll love the convenience and charm of this unbeatable location.

The Cooper House in Charlestown, MD

If you are looking for breathtaking views, great local dining, and a chance to relax with family and friends, then the look no further. The Cooper House in Charlestown, Maryland is a new waterfront property offering 3 individual suites or, for larger parties, the entire house with 4 bedrooms. Each suite has a private entrance, wi-fi, tv, individual climate control, and parking. Unwind on the two-tiered porch or sit by the cozy outdoor fire pit. The property owner lives on site.

The River House At North East

Relax with the whole family at this peaceful cottage located on the North East River, in a well protected anchorage, conveniently accessible to I-95. This home includes 5 bedrooms, 4 full baths, 2 living rooms, a formal dining room, 150 ft dock with 40 ft floating, a small sandy beach, and a 9 person hot tub. The lower floor is self-contained, but accessible with its own kitchen, living room, king bed and full bath. All floors have beautiful views of the Chesapeake Bay.

The Sunset House

Spacious 5-bedroom, 3-bathroom home in Charlestown, MD, perfect for families and groups! Enjoy 2 king beds, 3 queen beds, a fully stocked kitchen, and a cozy outdoor entertaining area with a grill, fire pit (wood provided), and a relaxing hot tub. Just 1.5 blocks from the Chesapeake Bay, with kayaks and paddleboards available for your adventures. Plenty of games included for added fun. Ideal for your next getaway! Bringing a boat? Utilize the mooring while you stay!

Waterfront Paradise on the Bay

This charming Red Point Beach home offers sweeping bay views and sunsets from a cliffside waterfront location. Our home has three bedrooms, one king, one queen, and one full over full bunkbed. The home features an equipped kitchen, washer & dryer, flat screen TV, gas grill, fire pit, outside shower and an 8 person hot tub. Just a short walk from a small, private bay beach this home is an idyllic retreat for those seeking both relaxation and adventure.

Cozy Log Cabin on the Bay at Sandy Cove

Tiny Home Nestled in the woods, this 600 sq ft, Conestoga Log Cabin is cozy & rustic, yet meets all of your needs. Sleeps 6-8 - Bedroom w/ a double bed - Bedroom w/ bunk beds - Open loft w/ 2 single beds - Living area with a futon - Kitchenette - Dining area - WiFi and a smart TV Stunning Location Sandy Cove is a Christian retreat center with 200+ acres on the headwaters of the Chesapeake Bay, offering beautiful views in all seasons.