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“Better than anticipated!”

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The Inn at Osprey Point
Ranked #1 of 10 Rock Hall B&B and Inns
Certificate of Excellence
Reviewed 21 May 2014

The Middle-Shore of the Chesapeake Bay in Maryland is made up of small, picturesque towns with mall shops and restaurants, not many "chain" businesses. For large scale events, such as a college graduation, lodging can be slim to none unless booked in advance. Such was the case for our family.We booked three nights a year ago for the graduation of our daughter from Washington College in Chestertown-about 20 miles away. The "chain" hotels there left lots to be desired and quite frankly we paid little attention to our booking until we arrived. What a surprise-the Inn is beautiful, service impeccable, food delicious! Terry and all the staff at breakfast were more than accommodating,Eric at the bar was wonderful as well as the rest of the wait staff. The rooms were quite comfortable and VERY clean. The Inn is situated on a marina, and the rooms reflect the nautical theme throughout. Several activities are available including boating and biking-which we were not able to enjoy because of our limited time.There is also a pool. Our experience here was far beyond our expectations and we are already planning a weekend in the fall. We love the Inn at Osprey Point!

  • Stayed: May 2014, travelled with family
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Thank DAW20639
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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237 - 243 of 351 reviews

Reviewed 18 May 2014

We just stayed at Osprey Point for the third time (second time at the annex) and I cannot say enough good things about it. In the area for our daughter's graduation, we had 2 rooms: Port and Starboard. The view of both the bay and Swan Creek from these rooms is stunning and the private balcony overlooking the Bay is a wonderful feature. The innkeeper is friendly and helpful. We needed to eat breakfast early and they were kind enough to accommodate us. This is our favorite place in the Chestertown/Rock Hall area and we will definitely be back.

  • Stayed: May 2014, travelled with family
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Thank clairenf
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 17 May 2014

The Inn at Osprey Point was a sweet surprise. Gracious hospitality and attention to every detail that makes for a relaxing time awaited us. We were treated to chocolate chip cookies at check in and then shown to our beautifully appointed room, Bolero, named for a sailing vessel. We were so cozy we didn't care at all about the heavy rains outside. We enjoyed a marvelous dinner at the Inn, and the breakfast was top notch. Lovely rooms, fine food, a staff that genuinely cares about the comfort of each guest, and fabulous views. We hope to return.

  • Stayed: May 2014, travelled as a couple
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Thank Betsy G
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 5 May 2014

Windingo, is our favorite room, we love the wonderful light coming through the windows. The staff is fabulous and they attend to all your needs making this a stay to remember. Terry the Innkeeper was especially helpful.
We stayed for 2 nights, Our discovery of Rock Hall included The Wildlife refuge,Watermans museum and Rock Hall Museum they were all very interesting. We had dinner at Natalie's at the Osprey Point and I had a wonderful shrimp dish, yummy. Waterman's on the Dock is the place for Crabs with a wonderful view and we also had some crabs at Fred's that were delish. The 4 pm sailing cruise on the Blue Crab off the Watermans Dock was amazing and serine. You will see the most amazing sunsets in Rock Hall. We will return for a 4th visit back in October.
Kathy Paziora and Nick Tumolo

  • Stayed: May 2014, travelled as a couple
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1  Thank KiKI277
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 5 May 2014

The Inn at Osprey Point is as close to perfect as you can get. The property is stunning, the rooms are well appointed and decorated (not to mention the local artwork), and the food fantastic. We stayed in the Captains Quarters and it felt like we were on a houseboat on the Chespeake without the wake. Most comfortable bed I've ever slept in outside of my own home. Immaculate!

Room Tip: Captains Quarters if available - request the Annex!
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  • Stayed: May 2014, travelled with family
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Thank Jennifer K
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 28 April 2014

Wonderful place. Stayed in the "Captain's Quarters" in the Annex. Great room, great location, great food (we ate dinner at the Inn's Restaurant as well as partaking in the Breakfast). Staff was perfect, helpful, respectful, courteous, etc. Would stay here again in a heartbeat.

  • Stayed: April 2014, travelled as a couple
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Thank Darren B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 28 April 2014

Each year my company hosts an over night retreat for our Internal Medicine residents during the spring. I decided to take a look at the Osprey Point since I had a very nice experience at the bar in their Inn as well as the beautiful setting of the property right on the water.

The events manager Casey Carol met with myself and one of the physicians to show us the accomodations and meeting space. Casey showed us every room in the Inn, Annex and the Farm house. Each room was unique, very inviting and had wonderful immenities from fluffy bathrobes to the package of freshly baked cookies left on every bed.

The transition from looking at the property to booking the property for our retreat was seamless. Casey made sure that she continued to answer our questions and was able to accomodate all of our special requests.

When the actual day of the retreat came I met Rita at 7:30 at the Inn to set up the meeting space. Rita made sure I had everything I needed for the meeting portion of the day prior to the group arriving. Once my group arrived both Rita and Casey constantly checked to see if the group needed anything. I never had to ask for beverage refills in the conference area and they were both as gracious as they could have been.

Since we wanted to keep all of the activities within the property we had lunch, dinner and breakfast the next morning all at the Inn. Lunch and dinner were pre-planned menus by their restaurant chef. The meals were delicious and the staff was again happy to accomodate any special requests that we had.

When we originally booked the property I was given the impression that the breakfast woulf be a "continental" type breatkfast. What we got instead was a complete buffet breakfast with home made quiche, muffins, french toast casserole, bagels, cereal, fresh fruit, juice, coffee, teas and so much more. The breakfast was phenominal and was the perfect start to what was going to be a day filled with physical challenges for our residents.

I am looking forward to booking our next year's retreat at the Osprey as well as hoping to take a couple of days to enjoy their facility on a personal basis. Without hesitation I would recommed the Osprey as a place to stay and dine.

  • Stayed: April 2014, travelled on business
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Thank Liz M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Additional Information about The Inn at Osprey Point

Address: 20786 Rock Hall Ave, Rock Hall, MD 21661-1405
Phone Number:
Region: United States > Maryland > Rock Hall
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Children Activities (Kid / Family Friendly) Restaurant Suites Swimming Pool Wheelchair access
Hotel Style:
Ranked #1 of 10 B&Bs / Inns in Rock Hall
Price Range: £103 - £148 (Based on Average Rates for a Standard Room)
Hotel Class:3 star — The Inn at Osprey Point 3*
Number of rooms: 17
Official Description (provided by the hotel):
The Inn at Osprey Point is an Eastern Shore waterfront property with three distinct accommodation venues. The Main Inn, colonial-style throughout the whole building, envelops seven charming rooms and Osprey Point Restaurant.The Osprey Annex, located on the Chesapeake Bay just 1/2 mile from the Main Inn, boasts six contemporary-style rooms. The beautifully renovated Farmhouse, with 4 bedrooms, is just a short walk from the Main Inn. It has become very popular for groups and gives the privacy and space needed. Room amenities can include a fireplace, whirlpool bathtub, king size beds, and excellent views of the Chesapeake Bay with romantic sunsets. Join us during the quiet season for a romantic getaway or just to relax. If you have an adventurous side, enjoy kayaking, swimming in our large pool, or participating in area activities such as visiting the nearby Eastern Neck Wildlife Refuge, fishing and sailing charters, shopping, and jogging/walking/biking our historic town. ... more   less 
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