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The Osprey Nest: Rappahannock Riverfront Suite

Sunny, private 2nd floor suite at the river's edge with panoramic views of the Rappahannock and surrounding farmland. Fiery sunsets, sunrises, starry skies, soaring eagles, and ospreys await. Swim, fish, explore the waterways by kayak, or bike in this tranquil, rural setting. Mornings on the balcony, with the songbirds is a treat, and relaxing on the riverfront "treehouse" deck, is sublime. Restaurants, historic sites, hiking, fossil hunting, wineries, antiques & more are a short car ride away.

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate a portion of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Treehouse Studio - kayaks included

Escape to the Treehouse in beautiful Urbanna! Our studio apartment is located in Fort Nonsense, a 3-story home with panoramic views of Urbanna Creek and the Rappahannock River. The Treehouse at Fort Nonsense is a peaceful getaway perfect for couples or solo travelers. **New in 2026** There is a new, queen-sized fold-out bed to replace the sofa bed and address negative feedback. This apartment is a unique space to work with, but we strive to provide a comfortable and budget friendly stay.

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with a kitchenette offers breathtaking 180-degree views of the Chesapeake Bay. Enjoy magnificent sunrises and stunning sunsets from your private deck, with the water’s edge just steps away. If you’ve ever wanted to experience life on the beach, this is as close as it gets. This suite reflects our love for the Chesapeake Bay and the relaxed coastal lifestyle, and we’re conveniently located just 10 minutes from ORF Airport

Waterfront on St. Leonard Creek at Fort Hill

Waterfront home on St. Leonard Creek w/ private pier for fishing and relaxing, PLUS a small beach area. Close to Solomons, fossil hunting at Calvert Cliffs, the Calvert Marine Museum (and their concerts), and other area attractions. Forget stairs! Our elevator directly connects the parking area to your private floor! Fort Hill is a uniquely quiet and private space with wide-open views of the outdoors. 4 kayaks are included FREE for you to enjoy!

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Captains Quarters Oasis Near Annapolis, Sleeps 4

This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!