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Breathtaking Waterfront - Christmas on the Water!

2027 Christmas is still available. Now booking for summer 2027. Serenity House in an incredible 4-bed 2-bath waterfront home - The ultimate getaway! Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - May** We do not have a separate stand alone hot tub. Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with/ docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2)

Entire home in North East, Maryland

Mason Lane Retreat – a private 432-acre Chesapeake Bay estate with stunning waterfront views in North East, MD. Ideal for executive retreats (up to 12 guests) or family reunions. Main House w/ 4 bds/ 2.5 ba fully equipped kitchen & gathering spaces, w/ an indoor exterior patio view. Private lake, kayaks, dock, fire pit & tiki bar. Just 4 miles from the quaint town of North East, shopping, antiquing, strolling Main Street, many local restaurants, coffee shops to fine dining! 1888 sq. ft. house

Charming Havre de Grace Home Walk to Downtown

This charming 3-bedroom, 2-bathroom home in historic Havre de Grace is the perfect mix of perfect location and relaxing getaway. Easily stroll to shopping, restaurants and nightlife in downtown Havre de Grace, or take a kayak down to the Susquehanna River. Three private bedrooms feature a king bed, queen bed, and twin bed. One bathroom has a tub-shower combo and the other has a stand-up shower. Kitchen has all major appliances and gadgets. Parking is free and plentiful. It doesn't get better!

Waterfront cabin home - 9+ private wooded acres

Gunpowder Cabin is a peaceful getaway set on 9+ wooded acres and a private drive in Northern Maryland, just an hour from Baltimore. With a half mile of hiking trails, and over 600 feet of frontage on Octoraro Creek, there are numerous options for taking in the natural beauty: warm up by our two firepits, lounge in a hammock, take a dip in the river, or fish for trout from the shoreline. A secluded retreat that feels remote, but moments from the civilization you came to escape.

Catching Sunsets on the Bay

Come and enjoy this brand new home, built for making memories on the Chesapeake Bay! Our spacious 3 bedroom, 2.5 bath is perfect for your next getaway. Our cozy, yet modern home is within feet of the Northeast River where you can take in the beautiful views, go kayaking, swimming or boating, or take a 12 minute drive to the new Great Wolf Lodge! Our home is perfect for couples or families as we have games, toys, and a pack n play if needed!

Cozy 4 BR 3 BA Near Chesapeake City

Peaceful, cozy modern cottage with many amenities in a water-oriented community along the Bohemia River. Just minutes from Chesapeake City and located across the street from the water. Our house is perfect for family vacations, tranquil retreats, girl/guy getaways, weddings, wedding guests. Two queen master BR’s w/private baths on the first floor, second floor has one larger BR w/twins and smaller BR w/daybed +trundle and shared bathroom.

Chesapeake Waterfront Vacation Rental with Dock

Relax at this peaceful waterfront vacation rental on the upper Chesapeake. 2 King beds, a Queen, a large Bunk bed, and a Day bed: 5 BRs, 2 Bath with spacious deck. 100 foot dock (has water and electric) with lots of room for water activities and fun in the sun. Tie off your boat or jet skis. 2 kayaks provided. Very clean and comfy. Linens and Kitchen amenities provided. All four 2nd floor bedrooms have smart TVs as does the living room.

Chesapeake Bay Cottage

This cozy home, just a block away from the Chesapeake Bay, offers the perfect mix of comfort, convenience, and outdoor charm. Tucked into a small, walkable neighborhood, the location is ideal for anyone looking to spend time near the water. Whether you’re planning a fishing weekend, a peaceful solo escape, or an exciting holiday with friends, this space offers the flexibility and ease that make everything feel effortless.

Magnolia House ~ Stunning beach sunsets!

Breath taking views of the beach with stunning sunsets over the water! Bring the whole family to relax in our traditional beach house. Betterton is known as the ‘Jewel of the Chesapeake’ and you will love the bay breezes from our deck that directly faces the water, and our screened in porch, perfect for board games or taking a nap! Inside is spacious and tastefully decorated. Outside is a gardeners treat!

The River House - waterfront

Relax with the whole family at this peaceful home on the Elk River. Enjoy breathtaking sunsets in the backyard overlooking the river. The kids will love running and splashing around in the yard. Outside patio features sectional sofa, Adirondack chairs and a fire pit to enjoy nights on the river. Plenty of restaurants and things to do in the area. Come enjoy the beauty of life on the Chesapeake!

HOOK WINE & SINKER sleeps 14 w/ Boat Slip at Inn

Welcome to Hook Wine & Sinker with dock slip at Chesapeake Inn!!! This 5 bedroom 3,400 sq foot home is the largest rental Chesapeake City has to offer. This home sits right under the famous Chesapeake City bridge and is a short walk to town and all it has to offer. The wide open floor plan makes this home great for entertaining.

Quarry Landing * River View & Pet Friendly

Charming 3 bedroom duplex in Historic Port Deposit, MD. Enjoy vintage style with modern comfort: memory foam beds, full kitchen, laundry, Wi-Fi. Walk to waterfront, dining, playground, dog park & more. Safe, quiet neighborhood—perfect for couples, families, or a peaceful getaway. Book now and enjoy a stay by the river!