Inn at Osprey Point

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.

We had my daughters wedding this past weekend and it was truly amazing the staff was great and the accommodations were top notch Deanna who was in charge of helping my daughter enjoy her day was the best! I would definitely recommend coming her even if it is just for dinner and a night. The chef did an amazing job preparing the food for the wedding could have asked for a better weekend. Thank you Osprey Poi nt!

The Inn is quaint and well-kept. The rooms and bathrooms (somewhat small) are clean and decorated tastefully. The staff members were pleasant and helpful. Right outside of the Inn, you will find a large marina where you can enjoy a nice walk. There are kayaks and bikes provided by the Inn for those who would like to partake. We also enjoyed a delicious dinner at the on-site restaurant.

A truly delightful inn with everything beautifully done. The main inn is lovely with Williamsburg-type decor tailored to the Eastern Shore. Our room in the Annex was large with a private balcony from which we could watch the boats and our own resident osprey. Everyone was so helpful for our micro-getaway. Rock Hall is a peaceful town with wonderful vistas and a great base for exploration. Dinner at the restaurant for my husband's birthday could not have been more delightful with creative dishes, graciously served in a space where one could have a quiet conversation. Breakfasts were delicious as well. Thank you! We will definitely return.

Booked two rooms for 3 adults and 4 children. Exceeded our expectations in all respects. Very relaxing getaway in an old-fashioned bayside retreat. Kids swam in the pool, played frisbee & tag, road bicycles around the property, explored the shoreline, etc., including my two boys catching a water snake. Lots of great water bird life around. Kids were too young for kayaking. Spend one afternoon at the nearby small sandy beach which was quite fun. We also had lunch and spent the afternoon in nearby historic Chestertown which was fun. There's an old fashioned luncheonette and bakery side by side which are wonderful, plus an ice cream shop. Some cute eateries in Rock Hall also. Osprey Inn is probably a bit boring for 1 child, but our small gang of kids had fun. No computers, no iPads and no video games for 3 days. The Osprey Inn restaurant was fantastic. The fillet mignon was perfect and I had the best Key Lime Pie in many, many years. Lastly, the employees at (and around) the inn are all so nice and helpful. Just wonderful welcoming people.