"Beautiful place with unique design who really make me feel part of the nature around."
David from United States
read full review
"If you love staying on the water, this is the place to stay!"
Diane M from United States
read full review
"Spacious suite (Escapade) at a reasonable price overlooking the water."
jjbren from United States
read full review
"The restaurant is fabulous. We had creamed soups crab cake entrees."
Liz G from United States
read full review
"The location was beautiful and so convenient to explore the Eastern Neck Refuge."
Linda from United States
read full review
3-star waterfront inn on Chesapeake Bay with free kayaks and bikes
Accommodations
The inn offers 14 uniquely decorated rooms with individual character and water views. Guests can choose rooms in the main inn or the Annex, with some featuring private balconies overlooking the marina. The Escapade junior suite has windows on two sides providing waterfront views of Swan Creek.
Dining
The on-site restaurant serves American cuisine and local seafood with a seasonal menu that changes based on local ingredients. Breakfast is included and served buffet style with homemade quiche, frittata, and French toast casserole. Dinner options include crab cakes, filet mignon, and Key lime pie, with the restaurant rated highly by previous guests.
Recreation
Guests have free access to kayaks, canoes, and bicycles to explore the marina and surrounding area. The property has an outdoor swimming pool with a view, a pool bar, and extensive picnic areas with BBQ facilities. A children's playground and kids' outdoor play equipment are available on the grounds.
Location & Nature
The inn is located directly on a marina with easy access to Chesapeake Bay for fishing and boating. Eastern Neck National Wildlife Refuge is nearby for wildlife observation, including ospreys, herons, and bald eagles. The property is a 9-minute walk from Waterman's Museum and within driving distance of Chestertown's farmer's market.
Pet-Friendly & Family-Friendly
The hotel offers pet-friendly rooms in select accommodations, with a dedicated ground-floor room for guests traveling with dogs. Family rooms are available with private bathrooms and balconies, and the inn provides board games and puzzles for children. Babysitting or child services can be arranged upon request.
Highlights
Location: Waterfront on marina, 9 min walk to Waterman's Museum
Recreation: Free kayaks, canoes, and bicycles for guest use
Dining: On-site restaurant serving local seafood and American cuisine
Wellness: Outdoor swimming pool with view and pool bar
Pet Policy: Select pet-friendly rooms with ground-floor access
Family: Children's playground and babysitting services
“Inn at Osprey Point provides a truly waterside experience, where spacious, clean rooms often open to marina views and serene sunsets. Mornings begin with a notable breakfast selection, and the inn's own restaurant is a consistent highlight for dinner. It's a place that invites return visits, with its pleasant staff and well-kept grounds adding to the appeal.”
James DavidEditor-in-Chief at Usmaryland
Select your room type
Inn At Osprey Point offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
King Room Sea View
2 persons
360 sq. feet
1 King-size bed
Air conditioning
Heating
room details
Queen Room Sea View
2 persons
240 sq. feet
1 King-size bed
Air conditioning
Bathtub
room details
Queen Room
2 persons
270 sq. feet
1 King-size bed
Air conditioning
Bathtub
room details
Show all rooms
Price and Room Availability Calendar
Check availability and prices for your dates now!
Facilities
Inn At Osprey Point offers amenities for your comfortable stay and unforgettable experiences
Facilities: Perfect
9.4/10Review score
General
No smoking on site
Wi-Fi
Parking
Pets allowed
Luggage storage
Allergy-free rooms
Smoke detectors
Electric vehicle charging station
Fire extinguishers
Key access
Sports & Fitness
Cycling
Guest Parking
Private parking is possible on site for free.
Services
Paid airport shuttle
Housekeeping
Welcome drink
Dining
Restaurant
Poolside snack bar
Picnic area/ Tables
Special diet menus
Business
Meeting/ Banquet facilities
Fax/Photocopying
Children
Cots
Babysitting/Child services
Board games
Children's menu
Children's play area
Spa & Leisure
Seasonal outdoor pool
Sun loungers
Garden area
BBQ facilities
Spa & wellness centre
Back massage
Full body massage
Pool with view
Shallow end
Room features
Air conditioning
Heating
Soundproofed rooms
Sitting area
Garden furniture
Tea and coffee facilities
Bathroom
Free toiletries
Media
Flat-screen TV
AM/FM alarm clock
Room decor
Carpeted floor
Show more
Dining Onsite
At the Inn At Osprey Point, vibrant dining comes alive at the Osprey Point Restaurant, where the rich flavors of American and seafood cuisines meet a welcoming atmosphere. A captivating bayside view enhances every meal, making it an ideal choice for those seeking culinary delight in a scenic setting.
Osprey Point Restaurant
American, Seafood
Ambiance
Traditional setting with stunning bayside views, creating a warm and inviting atmosphere.
Key Offerings
Signature dishes highlight local seafood fare, emphasizing fresh, seasonal flavors. Enjoy a leisurely dinner while taking in the picturesque surroundings. Perfect for special occasions or cozy meals with loved ones.
Reservation
Reservations are recommended for an optimal dining experience.
Queen Room2 persons270 sq. feet1 King-size bedAir conditioningBathtubroom details
Mgm National Harbor
Hyatt Place Ocean City Oceanfront
Francis Scott Key Family Resort
The Hotel At The University Of Maryland
Quality Inn Boardwalk
Castle In The Sand
Crystal Beach Hotel
St Michaels Harbour Inn, Marina And Spa
Rod 'N' Reel Resort
College Park Marriott Hotel & Conference Center
The Hotel At Arundel Preserve
Hotel Wheldale Hotel Castleford