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Inspiration Guest Suite - Cinnamon By The Bay

Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in Cinnamon By The Bay's in-town suites. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

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River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

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Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

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Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

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Totally Renovated historic house near town center

Renovated 19th century home with modern conveniences. 55” TV in family room, 2 more. 1st floor bedroom with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from Wash College and the C'town waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 more bedrooms with queens. 1 loft connected to a 2nd story bedroom with 2 twins. Fenced yard and an acre of private gardens. Fire pit. New Weber grill

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Kent Island Haven - A Waterfront Getaway

Located across the bay from Annapolis, Kent Island Haven is a convenient and beautiful alternative to a hotel. Near shopping, nature areas, and walking trails; as well as the fine restaurants and water-oriented features of the Eastern Shore. Convenient to Baltimore, DC, Easton and St. Michaels. This 600 square foot 1 BR/1 BA in-law apartment has a private entrance and full kitchen. Watch the ships and ospreys from the living room. Enjoy the waterside hammock, pier, patio, and garden.

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Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

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Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

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La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

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Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

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Cozy Waterfront Apartment Chester, MD

Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to enjoy water view!

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Pirates Perch

Rock Hall's most convenient vacation rental. Right on the parade route and walking distance to shops, ice cream, coffee, groceries and more! Sleeps 8 with 2 full baths. The master bedroom with full bath is on the 1st floor. Kitchen, dining room and living room. 3 TVs with WiFi internet. Off street parking for 3 full size vehicles.

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River front cottage with private dock & water fun

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Spacious4BR home with waterviews

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Waterfront Paradise w/ Pier - kayak to Chestertown

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Lark's Nest on the Chester River

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Away at the Bay: New Home on the Chesapeake Bay!

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Waterfront Chesapeake mansion - Panoramic Bay view

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Bay Home in Annapolis with Private Dock

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Private Chesapeake Bay Retreat w/ Bay Views!

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Riverfront Denton Estate on 7 Acres w/ Fire Pit!

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Chesapeake East Shore Chestertown, Pool & Dock

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Chestertown Watson Family Farm

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Welcome to Mermaid Haven!

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Cozy and Private Historic Cabin on the Water

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The Mariner's House

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Waterfront Guest House on 23 manicured acres

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Piney Grove Farm

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Cottage with Modern Updates - Walk to Waterfront!

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Entire River Front Home - 4 Bedrooms 4.5 Baths

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Gorgeous Creek Side Ranch-Style Estate With Dock

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Loon Cottage on Leeds Creek

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Owl Cottage - Cozy, Private & Walkable to Town

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Stay & Play by the Bay - Sunsets- 4 KING Bedrooms

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Downtown Historical Chestertown Lux Upstairs Apt

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Shore Harbor House on Kent Island

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