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Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

Chestertown - Eastern Shore Getaway

This century-old three-story home is in the beautiful historic district of Chestertown on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue. (NOTE - Airbnb adjusts our rate according to the current demand for rooms)

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 options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

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.

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.

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

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.

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided