Inn at Osprey Point

Our decision to stay at the Inn was last minute and we could not have been happier that we chose to stay there. The staff were the friendliest and the breakfast was tremendous. Sitting by the waters edge was extremely relaxing. We will be returning!

The Inn at Osprey Point was so beautiful! My husband and I went for just one night (for a wedding in the area). The staff was so nice and very helpful. The breakfast (included in your stay) was delicious! Our room was decorated colonial style, which I love. I would definitely stay there again and I highly recommend it.

This was our second year coming back to Osprey Point and staying in the Escapades room, which we love because it has the best view of Chesapeake Bay! The breakfast served in the morning is great, love those homemade quiches! Dinner at the restaurant in the evening was delicious, we were all very happy with the dishes we ordered and the service there is excellent, attentive, warm and friendly! Thank you again for hosting us, we all had a fabulous time and are looking forward to seeing you again next summer!!!

My wife and I enjoyed a warm and welcoming stay at The Osprey Point. Our suite overlooked the marina. We enjoyed the view in bed with coffee from the Keurig a few steps away. Breakfast by the fireplace was perfect. Our pre Valentine's dinner downstairs was another highlight. Crabcakes and tenderloin were as good as I have ever had. But the best part of our stay was the staff. Thank you everyone. And thanks for the Valentine Gift of chocolate strawberries and candy. A wonderful respite from a cold winter. ❤🕊❤

My husband and I initially booked a weekend getaway at Osprey Point Inn in September for our two year wedding anniversary but unfortunately we had to move our trip last minute due to a family emergency. The Inn was super understanding and kind about the situation which we really appreciated since we were going through a tough enough time as it was. We moved the getaway to November and actually really enjoyed being there during the off season. We ate dinner on Friday night at the Inn's restaurant and had a very pleasant experience. Everything was delicious and our server was very sweet and attentive. On Saturday and Sunday we enjoyed the complimentary breakfast before heading out for the day. Saturday we explored Chestertown and were delighted to be able to visit the farmer's market. We were also able to play pickleball and grabbed delicious sandwiches nearby at Fresh Start Food and Garden market before visiting Eastern Neck Wildlife Refuge. Everything was pretty close to the Inn via 15-20 min car ride. Our room was very cozy and clean. The only slight issue I had was that it was loud since it was near the door where all guests enter and exit the second floor. Otherwise, we loved our experience and hope to visit again soon in the warmer months so we can enjoy the amazing views of the marina along the property.

Food was fantastic and the bath towels were the thickest I have ever seen. Overall, a wonderful experience. Innkeeper Terry was very friendly as was the other staff we came in contact with. Great location for a small destination wedding with all the amenities you would need.