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Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Heron Roost

Heron Roost is a centrally-located waterfront apartment on a private gated lot with a heated pool. The view from your sun deck is the best on the property with spectacular sunrise and moonrise. We are conveniently located about one mile from the Chesapeake Bay Beach Club and twenty minutes from the US Naval Academy in Annapolis. There are numerous excellent restaurants and bars nearby and the towns of Easton and St Michael’s are close. Please come and enjoy our peaceful and unique property.

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.

Chestertown Private cottage with NFL Sun Ticket

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 the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

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.

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 the Cinnamon By The Bay Inn. 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.

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.

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.

Harmony Haven

Take it easy at this unique and tranquil getaway. Nestled in the woods, your stay is located minutes from Sandy Point State Park, the Chesapeake Bay Bridge and downtown Annapolis. A visit to Washington D. C. or Baltimore are only 30 minutes away. Enjoy kayaking or fishing at the community beach or bring a bike and enjoy the many trails or bike routes in the area. Please note, this unit does not have a full kitchen.