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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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Romantic private cottage - center of Chestertown .

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

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Mermaid's Getaway

You will be close to everything in Rock Hall when you stay at this centrally-located ground-level apartment. Just 1 block from Main Street, park the car and walk to everything Rock Hall - shops, marinas, grocery store, ice cream shop, coffee, boat ramps, and more. A full kitchen, comfortable living room, private entrance and backyard access await you. Large grassy yard with firepit, BBQ grill, and picnic tables. Great for playing or relaxing. This one bedroom apartment sleeps 4 comfortably.

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Elliott House Historic Home Near Chesapeake Bay

The Elliott House is located outside of Still Pond, MD. Mere minutes to Betterton Beach (1.5 miles), Downtown Chestertown, etc A historic cottage built in 1854, this location was formerly an old time general store. In the early 1900's it was a stopping place for soldiers stationed at nearby training camps and the upstairs served as a makeshift dance hall. Current owner has kept the historic charm but added a number of modern conveniences. In the heart of Kent County with rural scenery.

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1-br apt in downtown Chestertown (Unit 1)

Note: Beginning Oct. 4, 2023, we have eliminated all booking fees and cleaning fees. The price you see is the price you get. 1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.

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Bright, new apartment in the heart of Chestertown

Flooded with light and in the center of all Chestertown has to offer. Have a front seat to Chestertown’s festivals. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.

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DragonflyPeake Studio

Welcome to our cozy studio that we built for the comfort of our friends, family and Airbnbers. Our DragonflyPeake Studio is a centrally-located place. We are directly across from the Osprey and Haven Harbour Marinas and are in walking distance to the Ferry beach, Muskrat Alley for Breakfast and The Blue Heron for dinner and drinks. We are also a walk to town or bike ride. Enjoy a quiet cozy location with coffee or cocktails on the back deck.

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Relax Inn

We welcome you to relax in this comfortable space for two with a plush king sized bed and a private bathroom. Enjoy the high speed internet and 50 inch smart TV. The kitchenette is equipped with a mini fridge, microwave, Keurig and a table for two. A coded entry will open into your private space that is attached to our home but separated by a locked door. We love to offer early check-in and late check-out as our calendar allows.

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Knot's Landing, spacious Apt. downtown Rock Hall

Welcome to Knot's landing - a spacious apartment located above one of Rock Hall's favorite shops in the quaint Main Street corridor. Steps outside of your front door you will find a coffee shop, sweets / bakery shop, farmers market, ice cream, and more! Use the provided bicycles for quick access to other restaurants and marinas. Perfect place to stay to enjoy Rock Hall, Chestertown, and surrounding Kent County.

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Bayside Bungalow

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 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.

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Modern Lux First Floor Apt Historical Chestertown

Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a stone's throw away from the vibrant town center, you'll find a plethora of shops, cafes, and restaurants waiting to be explored.

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Downtown Studio Apartment

Studio apartment right in the heart of downtown Chestertown overlooking Fountain Park. Close to downtown shops and restaurants and Saturday Farmers market

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Historic 3 Bed Betterton Area Hideaway Near Bay

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RIVER WATCH

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Relax Inn

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Romantic private cottage - center of Chestertown .

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1-br apt in downtown Chestertown (Unit 1)

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Traveler Guest Suite - Cinnamon By The Bay

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Bright, new apartment in the heart of Chestertown

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Elliott House Historic Home Near Chesapeake Bay

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Historic 3 Bed Betterton Area Hideaway Near Bay

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RIVER WATCH

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Relax Inn

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Romantic private cottage - center of Chestertown .

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1-br apt in downtown Chestertown (Unit 1)

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Traveler Guest Suite - Cinnamon By The Bay

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Bright, new apartment in the heart of Chestertown

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Elliott House Historic Home Near Chesapeake Bay

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