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Vacation rentals in Queen Anne's County

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Top-rated vacation rentals in Queen Anne's County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Outrange at Blue Heron Farm
Farm stay · 4 guests · 2 beds · 1 bath

Outrange at Blue Heron FarmEnjoy 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 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.

Private Waterfront Rustic Gem w/Hot Tub and Pool
Entire residential home · 14 guests · 9 beds · 2.5 baths

Private Waterfront Rustic Gem w/Hot Tub and PoolEnjoy the beautiful outdoors at this rustic gem with all the amenities you seek. Sitting on 4 acres in nature's paradise with direct private dock access. You will get all the privacy you seek while being only 10 minutes from Kent Island and 30 minutes from Annapolis and either town has great shopping, restaurants and activities. Or sit back and relax at home pool side or soak in the hot tub and watch the sunset from the dock. So many choices to stay as busy as you desire during your stay.

Chester Riverfront At Kent Narrows
SUPERHOST
Entire residential home · 5 guests · 3 beds · 1 bath

Chester Riverfront At Kent NarrowsOur place is spacious, has great water views, a private beach and is close to restaurants and dining. You’ll love it because of the bay, hot tub, pool, and outdoor space. Our place is good for couples, friends, solo adventurers, and families with kids.

Vacation rentals for every style

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Popular amenities for Queen Anne's County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Queen Anne's County

SUPERHOST
  1. Entire cottage
  2. Chestertown
Sunview Cottage on Chesapeake Bay
SUPERHOST
  1. Entire guest suite
  2. Chestertown
Beautiful Waterfront Chestertown Getaway
SUPERHOST
  1. Entire guesthouse
  2. Grasonville
Eastern Shore Charm on Winchester Creek
SUPERHOST
  1. Entire residential home
  2. Grasonville
Serenity on the Shore - Chester River Beach
SUPERHOST
  1. Entire residential home
  2. Rock Hall
Pirates Perch
SUPERHOST
  1. Entire rental unit
  2. Chester
Cozy Waterfront Apartment on Kent Island
SUPERHOST
  1. Entire guesthouse
  2. Stevensville
Waterfront Getaway - View of bay from your bed
  1. Entire residential home
  2. Stevensville
Kent Island Waterfront Home with Amazing Sunsets
  1. Entire rental unit
  2. Chestertown
The Bittersweet
SUPERHOST
  1. Entire residential home
  2. Chestertown
CHESAPEAKE SUNSETS
SUPERHOST
  1. Entire cottage
  2. Saint Michaels
La Casita on Harris Creek, St. Michaels
SUPERHOST
  1. Entire loft
  2. Queenstown
Private Studio Loft with a Farm View

Top-rated things to do in Queen Anne's County

Unique activities hosted by local experts vetted for quality

  • Pole dance lesson
    Your experience will start with a sassy warm up and stretch. You will learn pole safety and basic grips and spins. We will break for photos and videos. We will wrap up with sassy choreography and another opportunity to record video or take photos. This experience is held at a private space. We can also work outdoors during the spring and summer seasons in Washington, DC if requested. Other things to note Shorts/sexy body suit and tank top are more suitable for the pole. Also wear clothing that helps you feel sexy. Bottled water is highly recommended.
    From Price:$32/person
  • Come Sail With Us!
    We're vaccinated for your safety and peace of mind! When you book our sailing experience, your payment goes to fund our non-profit outreach programs. Join our group experience as we sail around Baltimore Harbor and the Patapsco river (can be booked as a private experience as well). Do as much, or as little as you like. Take the helm, hoist and trim the sails, tack, jibe, or just sit back and enjoy the ride. We'll leave from Tindeco Wharf and sail out into the harbor. From there, we decide to sail toward the inner harbor or out past Fort McHenry, into the Patapsco river toward the Key bridge. This is a great opportunity to get more sailing time and develop your sailing skills under the watchful eye of a US Sailing Master Instructor Trainer. Never sailed before? No problem, during our time we'll teach you as much as you want. Just get away from it all on a relaxing sail? That not a problem either. Bring snacks and beverages to enjoy and just take in the breeze and enjoy the sights and sounds of sailing. Other things to note We're sailing on the 36' sailboat so it's not likely you'll get wet (unless it is raining). We will sail in light rain, but not in thunderstorms. If you enjoy your experience, it is okay to tip your captain and crew as you would any other in the service industry.
    From Price:$94/person
  • Sunset Sail with Wine and Cheese
    We're vaccinated for your safety and peace of mind! When you book our experience, your payment goes to fund our nonprofit outreach programs! Come sail with us and enjoy a beautiful sunset on the water! After a short safety briefing, we'll head out in to Baltimore Harbor to take in the sights of the city from the best vantage point, the deck of Condor, our 36' sailboat. While we're sailing you'll enjoy a glass or two of wine along with some cheese and crackers. As the evening winds down you'll enjoy the spectacular colors as the sun sets over Fort McHenry and the city. Other things to note Come prepared for a enjoyable sunset sail. Remember that it is typically cooler in the evening on the water, so a jacket might be a good idea. If you enjoy the experience, is it perfectly acceptable to tip your captain and crew as you would any other service industry.
    From Price:$156/person
  • Sailing Under the Stars
    We're vaccinated for your safety and peace of mind! When you book our experience, your payment goes to fund our nonprofit outreach programs! Enjoy and beautiful and peaceful moonlight sail on the water! Our experience starts at the dock, aboard our Sabre 36 sailboat, with a safety briefing. We'll motor away from the dock, hoist our sails, shut off the motor and let the peacefulness envelop us. We'll sail quietly along, taking in the background lights of the city. As we make our way into the Patapsco River, we'll enjoy the radiance of the moon and stars as they paint the night sky. We'll glide back to the dock as our experience ends, but keep the peacefulness and beauty in our memories to treasure forever. Other things to note Get ready to enjoy an unforgettable experience! As we move in to Fall, the evening temperatures may get cooler. It's probably a good idea to bring a jacket. If you enjoy the experience, it is perfectly acceptable to tip your captain and crew as you would any other service industry.
    From Price:$125/person
  • Sunset Sail w/Local Craft Beer
    Leave the streets of Baltimore behind as we set sail on the Chesapeake Bay. We'll meet outside of the The Inn At Henderson's Wharf and quickly hop on the boat. After going over safety basics, we'll sail out of the harbor and explore the Bay. The Chesapeake Bay offers a peaceful respite. If breezes are blowing, we can move quickly and feel the power of the wind. If the sea is quieter, we'll have a slower and more leisurely pace. Whatever the weather, time spent on the water is utterly relaxing. Nature lovers watch the active sea birds–ospreys, cormorants, terns, shoals of fish and rays. The sunsets are spectacular on the water. Other things to note If there's light rain, we can still have a great trip - sailing is all about being one with the weather! Heavy rain would require rescheduling or canceling.
    From Price:$138/person