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    View from boardwalk.
    Leo Y.

    A great place to stretch one's legs after a long drive. Right off route 50, with restrooms, information, playground, ample parking, and about a mile of boardwalk. Plenty of people fishing, kids playing on the playground, a few bikers and joggers on the boardwalk. If the boardwalk is followed under route 50, there is an impressive pedestrian bridge parallel to route 50.

    Caroline N.

    It was worth the pit stop =) I was driving on the bridge, on 50E towards Ocean City. My butt was hurting from driving about 2 hours, and I just randomly spotted a "park/grassy-lookin' area" from the bridge... and literally just took a turn off the highway and decided to just check it out and see if it was a nice view of the water... Although I only briefly walked around for 10 minutes, playing some phone games and whatnot - the view was WONDERFUL. Wow, you get to be literally right against the beautiful water AND bridge! I can tell this would be a great place to take the kids, as there are a couple playgrounds. As a grown adult, I passed on the playgrounds - BUT I LOVED sitting on the SWINGING BENCHES. There's multiple of them! =) What a nice touch!!! I didn't check out the bathroom/building facility, but it looked big from the outside. Pretty sure this place is kept up with maintenance - it was pretty clean in general, with no trash laying around. I think I'd come again if my legs start hurting from long drives to the ocean!

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    Review Highlights - Sailwinds Park

    There was also a shaded area to have a picnic, family swings and a nice view on the water and a bridge.

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    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!

    Holiday Inn Express Cambridge

    Holiday Inn Express Cambridge

    (20 reviews)

    $$

    This Holiday Inn Express isn't in great shape, and it isn't even the best Holiday Inn Express we…read morestayed in during our trip up and down the Eastern Shore, and normally a three star review is all we might be able to muster up given some grungy and odd things about the place. You know, the usual things: like a bathroom door that didn't latch, a dripping faucet, curtains that had an odd smell, kind of dim public spaces, the guy in the pool drinking beer and playing music from a boombox at top volume without any apparent relatives or companions actually using the pool --- all the usual things you get with a shop-worn lower middle end hotel chain like this brand. But: we had an extremely quiet stay, which is saying something given we had a view of the Burger King drive-through; the staff were exceedingly pleasant and professional; we got an excellent mid-week, off-season rate; and the room upon arrival was cleaner than the average room in this niche. And nobody seems to have gotten an ear infection from the pool and jacuzzi. So I just don't have the heart to rate this lower than four stars. We had a very pleasant stay despite the obvious limitations of the place.

    Room was absolutely fine - my one complaint is the connecting door to the next room let in a lot of…read morenoise from their TV. Breakfast was basic, served its purpose. Staff was friendly. Midweek August was about $140. Our little awards members gift was a bottle of water and potato chips.

    Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina - Health Club

    Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

    (299 reviews)

    $$$

    This is such a fun spot! I came here for a weekend conference and was able to take advantage of the…read moreamenities, but they had made to choose from. I enjoyed the pool, walking around the golf course and nature areas, fire, pits, and the feeling being secluded while also being across the street from a Walmart and some other retail. The indoor pool was family friendly, and had a hot tub you could be indoors or outdoors in, which was fun. They also had a hot tub outside closer to the water, but it was a little chilly so I didn't go out there. There were a ton of pools outside that looked nice even though I didn't take advantage of them The conference spaces made the work side of my trip easy since they have a variety of different meeting rooms and a larger spaces. Their channel is pretty good with two peloton and other machines and weightlifting areas. The meal options were pretty good for a hotel, the salmon over couscous that we had for dinner one night was really good. Coming to the eastern shore over the winter is always so peaceful and the Hyatt made it easy for me to enjoy it. The staff were friendly and helpful even when I messed up my booking, they were able to fix it right away.

    I wouldn't suggest staying here. On my last stay i observed such a toxic work environment that it…read morecarried over onto the guests. Free parking isn't everything. I attended a banquet and the food was phenomenal! Chef Nick came out and personally met with us at our request. The food he prepared was chef's kiss and this establishments ONLY saving grace. Top Tier Management: Start giving a care about your employees well being more and less about your dollar. Being toxic is so cringe.

    Sailwinds Park - venues - Updated May 2026

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