Vacation rentals in Queen Anne's County
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Queen Anne's County
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Chestertown
Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tollchester Marina featuring live music, dining and its own beach or a private community boat ramp to launch your water toys. This 800 sq ft 2 bedroom 1 bath house is located on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.
$193 per night
Rental unit in Chestertown
Secluded Cottage in Middle of Chestertown
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Enjoy the fire with views of nature all around, this is the perfect place to relax. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker. Comfortable queen bed, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a large house in front of the carriage house.
$170 per night
Guest suite in Chestertown
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.
$116 per night
Vacation rentals for every style
Get the amount of space that is right for you