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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.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

The Barn

Welcome to the Barn. It can host up to 4 guests. The bedroom is private with a queen size bed, a closet and a tv. In the living room there is a sleeper sofa that converts to a queen size bed. The living room tv can be enjoyed throughout as the space is open. Step out onto the porch and enjoy the sunrise in the morning and the horses throughout the day. The barn is only 35 miles to the beaches and only 12 miles to DE Turf. Within 1 mile you will find stores, dog parks and playgrounds.

Entire 1-Bedroom apt. - Private entrance in home

This centrally located, clean, 2nd floor apartment in our home is the perfect place to rest. Features very large bedroom with a new king bed with a hybrid mattress, and spacious living room with a queen size pull out couch. Well equipped kitchen with toaster oven, electric skillet, countertop burner, microwave, and coffee makers. Only 3 mi. to DE Turf, 15 mi. to Dover, and 30 mi. to the beaches! There are open stairs, so not appropriate for small children. Well-behaved pets welcome.

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.

Cozy Camper Escape Near Dover

Escape to a cozy camper in Hartly, DE! This stylish retreat sleeps 3 with a queen sized bed with memory foam mattress, and pull-out sofa. Enjoy amenities like AC, a fridge, freezer, 3-burner gas stove, oven, and instant hot water. A space heater is provided for chilly nights. Just 20 minutes from Dover attractions like Dover Motor Speedway and Delaware State University, it’s perfect for a peaceful getaway or event-filled stay. Book today for comfort and convenience!

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.