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Waterfront Chesapeake Bay Sunrises w/Private 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!

Blue on the Bay

2 bedroom cottage in historic Charlestown with screened porch, large yard & sitting area located in walking distance to the river and beach area. Walk to 3 local restaurants. Community playground, tennis courts, basketball court, pickle ball court, skate park & baseball field all in walking distance. Bring your boat, kayak & fishing poles. Boat launch available . Kayak, sup & pontoon rentals available. 15 minute drive to Great Wolfe Lodge. Monthly discount available, ask for details

Boho River Cottage

Chesapeake Bay getaway. Located on the North East River. The renovated cottage sleeps 4. Nap in our secluded backyard gardens. The cottage includes water access, kayaks, bikes, and a SUP board. Explore the town of NE to shop & dine in the region's top restaurants. Minutes from Elk Neck State Park, offering hiking, fishing, bird watching & mountain biking. Visit historic Havre de Grace, the Hollywood Casino, or relax and catch a sunset and the cool breeze coming off the North East River.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

Escape to Serenity: Chesapeake Bay Oasis Experience the ultimate Chesapeake Bay retreat - stunning 6-bedroom, 3-bath water-view villa, perfectly suited for family reunions & special gatherings. Enjoy breathtaking bay views, steps from the water's edge, with gated 240’ pier, sandy beach, protected swim area, picnic tables, BBQ grills & children's playground. .

Heron Creek- Historic home on Main Street

Beautiful home located in the heart of downtown. This 3 full bath/3 bedroom was recently renovated. Original hardwood floors throughout. This is an older home with narrow steps. It offers off street parking & is walkable to shops, restaurants, water sports & bike rentals. Close to Turkey Point Lighthouse, the park, fishing, boating & hiking.

Sunset Haven on Sue Creek

Unparalleled Sunsets on the Water! This unique simple renovated cottage, offers an amazing waterfront experience with a private sandy beach, amazing nightly sunsets and a 60 foot pier which can hold most vessels up to 45 feet. Owners are very friendly live next door and are happy to help make your relaxation complete.

Quiet Waterfront

Waterfront guesthouse in gated community on a creek off of the Severn River with clubhouse, swimming beach, tennis court. Approximately five miles from downtown Annapolis. NO PETS, NO SMOKING, NO PARTIES. Parking for up to four cars only. Anne Arundel County License Number STR-120.