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    Miles River Guest House

    5.0 (1 review)
    Closed 9:00 am - 6:00 pm

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    10 years ago

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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

    4.5(2 reviews)
    7.6 mi

    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!

    Photos
    Osprey Point Retreat and Conference Center - View from 1/4 mile-long pier.  (The longest on the Chesapeake Bay.)

    View from 1/4 mile-long pier. (The longest on the Chesapeake Bay.)

    Osprey Point Retreat and Conference Center - 2nd floor room w. water views.

    2nd floor room w. water views.

    Osprey Point Retreat and Conference Center - Sunset over the Chesapeake from the end of the pier.

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    Sunset over the Chesapeake from the end of the pier.

    Rehoboth Guest House - Beautiful day on the porch!

    Rehoboth Guest House

    4.7(69 reviews)
    55.9 mi

    Where to begin about this place? I just loved it so much. I've been going to Rehoboth for quite a…read morewhile now, and I've always been enchanted by the exterior of this place; the plants, the awnings, the big wraparound porch all seemed so lovely. So when I booked my own trip to Rehoboth for the first time with my girlfriend, RGH was definitely on my radar. Imagine my surprise when the rooms were incredibly reasonably priced -- far better than any other hotel around. Throughout our stay, everything was so wonderfully handled. The staff was incredibly nice and personable, our room was cute and comfy (with really powerful AC, YAY!), and the breakfast was delicious. There are so many cute little nooks around the house to eat or hang out in. And if you're worried about sharing a bathroom, don't be -- they were so incredibly clean, and I only had to wait once. The one thing that worried me was the fact that I've mostly seen an older crowd here, but we weren't treated any differently for being younger, and of course the place is incredibly LGBTQ+-friendly. My only regret is that I didn't get to see the dog! In case you couldn't tell, I highly, highly recommend Rehoboth Guest House, and I hope I have the pleasure of staying there in the future :)

    This place is so nice and very homey but I do recommend getting a room with its own personal…read morebathroom....sharing a bathroom is not fun but we still enjoyed our stay immensely.

    Photos
    Rehoboth Guest House - Hallway on 1st floor (so clean!)

    Hallway on 1st floor (so clean!)

    Rehoboth Guest House
    Rehoboth Guest House - Breakfast

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    Breakfast

    931 Beach

    931 Beach

    4.4(10 reviews)
    65.3 mi

    We love the 931 Beach house! My moms cousin and her husband own this beautiful property and for a…read morewhile my grandmother actually managed it. It has been recently renovated and painted! Right across from the ocean, the historic building is on a street with cute victorian inns, and when you sit on the porch you can see down the row, or stare off into the waves as you breathe in the salty air! There's quite a bit to do in the area, including different trolley tours (we did the ghost one) which are a ton of fun! Plus an awesome outdoor shopping area with some great restaurants (such as The Blue Pig). I reccomend 931 Beach House to anyone looking for a historic building that's been well preserved with adding light modern touch. A beach town with cute shops and restaurants make this a great destination for couples and families alike, and being on the smaller side keeps the inn well maintained and makes you feel special when you stay. If you're heading to Cape May, definitely check out the 931 Beach House, you won't regret it!

    This is one of the best bed & breakfast houses I've been to - location, location, location! The…read morebeautiful blue house is opposite the ocean and renting there I had the added convenience of easy parking - and access to beach chairs right under the house. The bedroom balcony was huge and beautiful, affording me a panoramic view of the ocean 24/7. At night I kept the balcony door open and fell asleep to the sound of the ocean roaring across the way. Everything I needed was inside the room - kitchenette, large shower, smart tv, lamps, extra lighting, and lots of towels. The innkeeper Liza is such a beautiful person and extended herself to me beyond what I expected. I wasn't sure how to get there and she offered to pick me up from the station - so sweet. I love her! I ended up driving in but it's the thought that counts. It's not every day that people offer things they don't have to do. The beach is clean and felt really private in October. I'm sure the summer is more packed, but it can't be that bad because Cape May itself is just beautiful. There are restaurants, clothes, souvenirs and so much more to do on that strip. I can't wait to go back there.

    Photos
    931 Beach - Back house entrance.

    Back house entrance.

    931 Beach
    931 Beach - Wrap around deck.

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    Wrap around deck.

    Miles River Guest House - guesthouses - Updated June 2026

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