Osprey Point Inn

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.

My wife and I got engaged and married at the Osprey Inn. We were introduced to the Inn by friends and this is our GO TO place on the Chesapeake Bay. We love the staff who are incredibly kind and thoughtful. The breakfast is THE BEST with new varieties of quiches and French toast flavors every day with other favorites. Terry is there most weekdays for breakfast and is always good for friendly conversation. She always goes out of the way to check on us and make sure things are good. Even when power was out during a storm she made sure we were comfortable and offered to let us eat dinner in their fabulous restaurant when it wasn’t open. The views of the sunset from the Annex rooms are breathtaking and the best around. We love the Forward room as our favorite. Just don’t tell anyone. We don’t want it to get too booked up this summer! If you like small Eastern Shore towns, Rock Hall is the jewel of the Chesapeake and you will enjoy the small town ambience.

Beautiful views, great amenities, and friendly people. The room was very quaint, clean and cozy. The staff was more than accommodating and willing to help. We stayed at the starboard room and the views were fantastic. Highly recommend and we will be back.

Came with our kids for a mini spring break trip and we had such a lovely stay. The staff was so friendly, pointed out an eagle nest to the kids. Took the canoe out twice, sunset at the beach, amazing breakfast at the inn every morning. We stayed in the Escapade room which has an amazing view of the water and was very comfortable for parents + kids. Would absolutely recommend.

Fantastic place. Perfect for getting away from it all. Breakfast was well made and tasty with plenty of options. We initially tried to do our typical vacation behavior of looking for "something to do". Turns out, you're about an hour away from everything. So, there was nothing to do, but that turned out to be perfect. We started the day by sitting by the marina and reading. Then we'd down most of the day by the pool where we had drinks and food from the pool bar & grill. We didn't have a reservation for the Osprey Point Restaurant, so we left the inn to go to the Blue Heron for dinner. However, later that evening we sat at the bar in the restaurant at the inn to have Bananas Foster for dessert. The only downside was the rooms are above the restaurant, so you get quite a bit of sound through the floor from the people dining in the restaurant in the evening. However, while it was noticed, it wasn't enough to detract from our stay.

What a gem! We spent a perfect fall weekend at the Osprey Point Inn. The Inn is in a picturesque setting, with the grounds well kept and the view of the water and docked boats relaxing. Our room (Bolero) was so nice, with a gas fireplace, sitting area, and poster bed. We enjoyed a delicious dinner at the restaurant. (My husband loved the wedge salad and his crab cake. He also enjoyed fried oysters as an appetizer. I enjoyed my soft shell crab). Breakfast was one of the best we’ve had at a bed & breakfast. (Highlights were the lemon French toast, two types of frittatas, and amazing sausage gravy and biscuits. There was also assorted breads and pastries, with cereals and yogurts). Every staff member we encountered was very friendly and seemed like they genuinely enjoyed their work. Such a pleasant stay. I can’t wait to return!

Had the pleasure to celebrate our wedding at Osprey Point in November. From Deanna on down the staff was incredible and made our big day everything we could have hoped for.

Our stay at Osprey Point was absolutely wonderful! The staff was warm and welcoming, the rooms were beautifully appointed, and the views were simply breathtaking. We’ve been coming here for over 20 years and just absolutely love this place and the incredible staff. A perfect getaway—we can’t wait to return! The Emery’s Catch My Drift Sea Glass Creations