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    The Oaks Waterfront Hotel - Water View Event Space

    The Oaks Waterfront Hotel

    (31 reviews)

    Lovely place, extremely responsive staff, and nice amenities. What more do you want? We spent 3…read morenights there in August and had a lovely time. Room was decent size, and bed was excellent. Sat outside in the early morning and watched the sun rise over a cove. Took out kayaks and paddleboards in the afternoon, and then had a drink. Ate dinner one night at the restaurant, and it was good. The breakfasts were fresh-cooked each morning, and substantial. They have a Keurig and other free drinks 24/7, which is good for me because I wake up before dawn. We did have a couple of minor problems, but the staff took care of them immediately and without any fuss. I really appreciate that type of service because often you get a reluctant and slow response, or the hotel doesn't have the resources to fix the problem. If there's one thing to warn about, it's that The Oaks is heavily into the wedding business, and that drives its entire strategy. So you can't get a room on a weekend if there's a wedding booked, and you can't get into the restaurant for dinner, either. And thus on the nights when you can get into the restaurant, it's typically full because folks from the nearby towns like to come, plus the hotel guests. If you see a complaint on Yelp, most likely it's due to the rather limited access to the restaurant and the weird rules about when it's available. In sum, this is an expensive place, but it's worth it for a quiet, romantic, scenic getaway.

    We came here for a Valentine's Day weekend getaway. Hotel communicated our arrival via text, very…read moreconvenient. Upon arrival we were given a tour of the hotel which included the bar and restaurant. Room was very spacious and clean, plenty of drawer storage space but not a lot of closet space. Bathroom was gorgeously designed, opened, and had very nice heated floors! The bed was also super comfortable. Can hear music from the restaurant downstairs, would definitely recommend bringing a white noise machine. Breakfast is chef made & included in your stay, which was so convenient & delicious!! The hotel is around a 10 min drive to St. Michael's. On our last night we got stuck on the western side of the Bay Bridge & had to detour around the Chesapeake. We called the hotel & they graciously gave us a late check out the following afternoon. Staff is very attentive & kind! We will definitely be back in the peak season!!

    Osprey Point Retreat and Conference Center - Dining/conference on lower level, rooms above - all with spectacular views.

    Osprey Point Retreat and Conference Center

    (2 reviews)

    Located 90 minutes from Baltimore and Washington, Osprey Point is a serene and spiritual place that…read morefeels like the large home in which I'd like to live someday. Both secular and religious organizations host conferences here. Amenities include a large meeting room, free WiFi, office services for printing and faxing, tennis courts, a swimming pool and jacuzzi, a library, a chapel, workout facilities, recreation room with pool table and fireplace, a top chef (Dawn McLoughlin), and, of course, spectacular views of the Chesapeake. It is the perfect location for your next gathering (from 10 to 50 people). Golf, bay cruises, kayaking, and the charming town of St. Michaels are all within 20 minutes of the property. The property is operated by the Trinity Forum (www.ttf.org), a D.C.-based Christian 'think-tank' whose mission is to renew Christian culture and to promote human freedom and flourishing. The property is home to the Trinity Forum Academy (academy.ttf.org), an organization that annually enrolls approximately a dozen 20-somethings for a post-graduate year of study on an aspect of Christianity of interest to them. The fellows are housed in a separate building on the property.

    I spent the weekend at Osprey Point Retreat and Conference Center to conduct a site visit for my…read moreclient groups. I wasn't sure what to expect since it appeared to be in the middle of an extremely small town but not the usual B&B that you find in these rural Eastern Shore areas. Gorgeous tree lined and winding roads on the way in, bayside homes with tons of land, horse farms; everything you'd imagine a postcard to look like. We encountered about 20 deer bounding in front of us and luckily we were only going 3mph and able to stop. It was unlike anything we've ever seen. The land is protected and wildlife such as rabbits, geese and white tail run freely to the waters edge and back into the woods. Upon arrival, we toured the rooms and grounds. The property itself has one conference room and flexible small group event spaces designed to facilitate group discussion and reflection. Each of the 25 sleeping rooms has its own distinct design, simple and indicative of the region. Some rooms have porches and many face the water. It's awesome just to sit and listen to the water. There are no televisions in the rooms, so come prepared to RELAX and UNPLUG! The living and game room were comfortable and relaxing and do feature a television as does the small gym. The GM is gracious and hospitable and lives on the grounds and easily accessible. I will say for the city slickers and those unfamiliar with the area, do not expect a high end, boutique B&B catering to couples and others looking strictly for a getaway for the weekend. This functional venue and its space is designed and ideal for small social, civic, church and gov't groups. The grounds are shared with the Trinity Academy, a group of students completing a 9 month spiritual fellowship. The students make up most of the staff. It's great for off site retreats and brainstorming sessions with teams and leaders. Seems great for family events such as small and intimate vow renewal and weddings who want the feel of a B&B but need something a bit larger (keep in mind, there are 25 sleeping rooms). The city is small but within close proximity to St. Michaels and Easton. After my weekend, I decided to really start focusing on what's important and trying my best to SLOW down and appreciate the smaller things. It really does only take a couple days away from it all to see the difference a change of pace really makes. My husband commented the time seemed much slower, the days longer. Don't we all want need that sometimes!

    Chesapeake Paradise

    Chesapeake Paradise

    (5 reviews)

    Absolutely Unforgettable Stay -- A True Hidden Gem!…read more Stop looking and book it -- seriously! This hidden gem is truly a take-my-money kind of place. With a snowstorm just having passed and a last-minute plan to celebrate my daughter's 22nd birthday, we were so lucky to come across this beautiful home. Although we're a big family, this trip was just five of us -- and wow, there was more than enough space. In fact, I've already started planning future bookings because this will definitely be our yearly getaway spot. The views are stunning, and the home feels exactly like that -- a home -- with a modern touch that makes everything feel fresh, comfortable, and welcoming. The location was also very easy to find, which made arrival stress-free. Everything you need for your stay is thoughtfully provided. The house is HUGE, but not in a cold or empty way. As soon as you walk in, it unfolds like a story -- you can truly feel the love, care, and appreciation that's been poured into this place over time. There are multiple sitting areas, plenty of space for gatherings, and so many little touches that make it special. The host went above and beyond. They were incredibly accommodating and even answered a question for us at 1 a.m. -- something I fully expected to wait until morning. That level of care says everything. This host genuinely takes the extra mile to make sure you're comfortable and well taken care of. We visited in the winter with lots of snow, and it was magical. The Chesapeake had frozen, and we were actually able to skate on it safely -- an experience I'll never forget at 43, and one my children will always remember too. I can already imagine how amazing this place must be in the spring and summer with fishing, swimming, and endless outdoor activities. No matter the season, this is an incredible place to stay. The balcony views alone are breathtaking -- and if you're a photographer, this spot is a dream. Thank you for helping us create such beautiful memories. We'll definitely be back!

    Beautiful setting and wonderful group of women. Enjoyed the whole weekend. Have also loved having…read moreone on one talks with Shawn.

    Chesapeake Bay Maritime Museum - Beautifully restored lighthouse

    Chesapeake Bay Maritime Museum

    (56 reviews)

    BLUF: A wonderful museum consisting of 18 acres, many buildings and even a river cruise, telling…read morethe history about the Chesapeake Bay. Chesapeake Bay Maritime Museum is one of those museums that I enjoy visiting every few years. Since they recently opened a new building I was excited to check it out. With limited time to explore, I stuck to the new building which has their admissions/ticket counter, various types of Chesapeake Bay boats, a well curated display case of ship models on display and a lovely gift shop. Oh, and let's not forget Sailor the Iron Dog! Two of my all time favorite exhibits at the museum are the display of oyster cans and the crab picking machine. I laugh every time I see the crab picking machine and I always marvel at all of the big oyster cans. Being able to go inside the Hooper Strait lighthouse is also fun. The Chesapeake Bay Maritime Museum has lovely views of the river from shore but those who want a better view can take a cruise or sail on one of various historic vessels. Another things that makes CBMM great is its plentiful parking and close proximity to downtown Saint Michaels.

    At $20 per person, Chesapeake Bay Maritime Museum was a bit of a letdown…read more They currently have an exhibit entitled "Sailing to Freedom" and that was the main reason for our stop here, especially considering we have recently visited a different nautical museum which was similarly priced and fantastic. Unfortunately the exhibit was small and, if I'm being honest, boring. The grounds here are not very large and are composed mostly of old wooden boats, bells, and a lighthouse, which was by far the highlight of our visit. They claim that the grounds are dog friendly however there isn't much to see outside so I would not recommend bringing a dog. I wouldn't personally recommend bringing children either as it doesn't seem like they would have a good time here. There were five or six children present during our visit and they were literally just running in circles on the grass. I understand that our visit was during the off-season but it was a wasn't a very good use of time or money in my opinion.

    The Willow Grande - venues - Updated May 2026

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