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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Annapolis reviews

  • Loved it - again!

    "We've stayed at Chestnut House for 3 summers in a row and it was just perfect, again! My son now refers to it as "home during the summer." We love the quiet and calm - I can really feel myself relax as I drive up the driveway. Our hosts and the farm manager were super - very attentive and helpful. Close to downtown Annapolis and the Naval Academy. We love everything about it, and hope to be back next year!"
    Guest: Deb G Date of Stay: June 2016 Review Submitted: July 20, 2016
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  • 29 Jeremy's Way

    "My family and friends truly enjoy staying at this property. We park our cars and enjoy all of Eastport and Annapolis by foot. 29 Jeremy's Way is always kept in imacullate condition inside and out. It's a wonderful base location for sailing and sightseeing enthusiasts alike. The owner has been nothing but accommodating and helpful. We can't wait to schedule our next trip to Annapolis!"
    Guest: Ellen M. Date of Stay: July 2016 Review Submitted: July 10, 2016
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  • fantastic home with lots of fun for kids.

    "I stayed for a weekend in June in this house with 4 families. There were 8 kids between the ages of 10-13. We were in Annapolis for a lacrosse tournament. We loved this house. The kids played and played outside in the large fenced in yard. We had big dinners both nights and the kitchen was perfectly stocked. There was tons of seating for everyone both inside and out. We stayed out on the large deck at night. The bathrooms were fantastic and the beds were very comfortable. I would definitely recommend this house to anybody who is looking for a stay with their family or multiple families. The homeowners actually live in this home and move out for the time that it is rented. We had a small situation with the home protection alarm and the homeowners took care of the situation immediately. Thank you so much Quinn and Erin. We will cross our fingers that we have lacrosse tournaments in Maryland again next year because we would love to come back."
    Guest: Laurel G. Date of Stay: June 2016 Review Submitted: June 23, 2016
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  • fabulous and just gorgeous views

    "Wow, this was like a step into a european country home....gorgeous views from all outside decking, enjoyed watching the boats all day long. Beds were terrific and house and furnished and can easily entertain or go to easy access downtown Annapolis and the waterfront for shopping and restaurants Toured the academy and took day trip to Washington DC it was great to come back to such a comfortable place to stay. Owner is extremely accommodating.....Eileen and John O'Toole"
    Guest: none Date of Stay: September 2015 Review Submitted: September 19, 2015
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