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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 - Living/Dining/Communal area at the Rehobeth Guest House

    Rehoboth Guest House

    4.7(69 reviews)
    55.9 mi

    Hear me out with this review:…read more I have never stayed in a Bed & Breakfast house before and when I was initially trying to book somewhere to stay in Rehoboth Beach this was the first place suggested. The house contains rooms with private bathrooms and rooms on a floor with shared bathrooms. I was very hesitant to book at first when I read that I would have to "share" a bathroom. We just returned home after a 4 night stay here and we were more than satisfied! Tom, the house owner, is super kind, personable and hospitable. His other workers (Rayvn and Chris) are also so helpful and always get you what you need. You can request to have breakfast in the morning from a menu selection and they bring you your food out at the time you request to have it ready for you . Tom always came and checked up on us wherever we were sitting during breakfast to chat about random things, show us his puppy and ask us if we wanted more food or needed anything. The room we stayed in had a shared bathroom in the hallway (we stayed on the 2nd floor and other rooms shared 2 full baths and a half bath with us) and it was actually very clean. The staff did a good job replenishing towels each day and cleaning the shower/toilet/sink. Felt very comfortable here. We would love to try a room with a private bathroom (it was so booked up when we tried to get one initially so book way in advance!) I love that the beach was only a 4 minute walk and access to the main streets was only an alley walk away from the house. No complaints at all after this stay. When we sat out on the porch each morning and night, many people would walk by making comments about how pretty and interesting the establishment was. The interior of the house smells super good and is clean. Highly recommend staying here! Overall 5/5 stars and we will definitely be back next year

    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 - Tom the InnKeeper (in the middle) was a very gracious host.

    Tom the InnKeeper (in the middle) was a very gracious host.

    Rehoboth Guest House - Beautiful day on the porch!

    Beautiful day on the porch!

    Rehoboth Guest House - Off Season Retreat I needed to be away from home to regain my energy.  In addition to hot omelette, this is how I was treated for breakfast.

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    Off Season Retreat I needed to be away from home to regain my energy. In addition to hot omelette, this is how I was treated for breakfast.

    Miles River Guest House - guesthouses - Updated September 2026

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