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    The Oaks Waterfront Hotel

    3.9 (33 reviews)
    Open Open 24 hours

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    Spinach & mushroom omelette
    Hiro H.

    We came here for a Valentine's Day weekend getaway. Hotel communicated our arrival via text, very convenient. 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!!

    our table at the rehearsal dinner

    We just had our son's wedding at this incredible venue. To begin with the staff was fantastic and anticipated your every need. Anything we asked for was taken care of in seconds. Everyone was kind, personable, and so helpful. What makes the Oaks stand out is not just their beautiful vistas, elegance and charm but the variety of these traits. Our first event was the rehearsal dinner on a magnificent, covered dock with the wind gently blowing as we enjoyed a delicious Chesapeake buffet. (picture below). For appetizers before, we were on a second-floor deck over a full landscape of water. The wedding took place on a lawn that was reached by walking over a charming and lovely bridge and as the ceremony took place you could see the birds flying and fish jumping against the glorious backdrop of the water as the bride and groom said their vows. The reception was in a gorgeous ballroom that had the coolest decoration. There were no boring white table clothes but cool chairs and tables and ribbons hanging from the light fixtures. That must have taken someone hours to do. But it was so festive and unique. Then that same ballroom was transformed into a cozy brunch area the next day. Everyone had such a marvelous time and all the guests commented on what a wonderful venue it was. We could have booked down the road and been one of two or three other weddings but here we had the whole place to ourselves. It was perfect!

    Win S.

    Gorgeous venue! Stayed here over a holiday weekend in the wintertime and it was quiet, serene and practically empty! (just 2 other parties). I'd love to come back when it's warmer and experience this beautiful place when the temperatures are right to enjoy the outdoors. They have their own dock (so pretty!! there are chairs to sit and relax) and a private patio space. There's also a side, private cottage that can be rented out that features a kitchenette and spa tub next to the main inn. I reserved a King bedroom in the main inn; I made a point to ask for one of the rooms that faced the waterfront area. The receptionist also generously honored and price matched the cost that I saw on Booking.com the day before! Loved the view from my room! The furniture is old English countryside and quaint. Not my usual taste, but it fit this inn's style. It seems like the place was renovated not that long ago, too. Our room also came with a mini fire place that you can turn on and off. So cozy! I was hoping for a bigger tub in the bathroom, but it was a regular shower + a slight minus that the bathroom was in older condition. The inn-keeper was very friendly and welcoming, making sure that we were doing well and was quick to offer advice (told us what to do in the town and where to shop and eat). We took his advice and tried the Talbots restaurant, which was excellent! In the common areas, they offer sugar cookies in the late afternoon. I didn't get to try them because we were late to come back after dinner. They also have a communal mini fridge in the living area where you can enjoy complimentary wine, beer or soda! What a nice touch! Breakfast is served at 9 a.m. on the house. That was my favorite experience at the inn! We ordered the omelet and French toast. They were perfectly cooked with gorgeous presentation. We also had an appetizer of a fruit cup with freshly cut strawberries and a tarragon sprig to top it off (who knew that tarragon would go so well with fruit!) The lighting in the dining room was exquisite. It would be a cute venue for a special event like a wedding. Apparently, they host about 42 weddings a year - so busy!! So make sure you come on a weekend where there's not one.

    Beth S.

    My son and new daughter-in-law were the first wedding at the newly refurbished Oaks Waterfront Inn. I can only say WOW!! The Oaks is spectacular! The decor is soothing and beautiful and the grounds are gorgeous. The food is fabulous and the service is impeccable. The team at The Oaks is professional, knowledgeable, gracious and caring. They were easy to work with and took care of every detail. We could not be more pleased with the wedding weekend!! Run, don't walk, to book your event at The Oaks!

    The meal served at The Oaks from a wedding I attended.
    Christina P.

    Not great for an outdoor wedding if it might rain. I attended a wedding ceremony that was held under the covered dock. We sat in the back and couldn't see or hear everything. There was also rain, wind, thunder and lightning! Not pleasant. The one AWESOME thing was the meal served for dinner. (I posted a photo on Yelp) it was a Maryland Crabcake that was leaning against a perfectly cooked medium-rare steak that was topped with sautéed shiitake mushroom caps. Underneath the steak and Crabcake were freshly cooked green beans (huge difference if you normally eat yours from a can). There were also small round, peeled potatoes evenly spaced around the plate. The best part was the creamy and buttery, with a hint of salt, oyster sauce that everything was sitting in. No oyster taste though. SO DELICIOUS! I want to eat that meal every day for the rest of my life.

    Room With a View
    Buzz B.

    Our daughter's wedding was at The Oaks this weekend. This was a wonderful location for a wedding. It was really neat to have the entire location booked with family and friends. It made the weekend feel like it was our own personal resort. Our room was large, clean and had a great view of the water. When we were ready for shopping, downtown St. Michaels was only 3.5 miles away. The town had plenty of bars, restaurants, and shops. For the wedding, a family room is provided for lounging during the day and served as an area for everyone to check in periodically. The organization of the guests arriving, hot coca with schnapps, moving to the wedding service on the dock, to the cocktail reception and to the dinner was smoothly handled. The dinner was outstanding. The service was remarkable. I would definitely recommend this location for a wedding.

    The Oaks goes beyond a wedding venue. This place is a home for the most memorable and important weekend of your life! Every single person involved goes above and beyond to make sure the bride and groom, plus family and friends are well taken care of. The food is phenomenal, service is perfection, atmosphere is incredible. Everything is immaculate. My husband and I and our families cannot thank this venue enough, during a time of unknown and a pandemic they worked endlessly with us to make our entire weekend unforgettable. It was better than I ever imagine and the butterflies will last a lifetime. You need to check this venue out! Tracey, Candy, Katie, missy (& everyone!!!) are insanely generous and kindhearted people. Forever grateful.

    View of The Oaks from the creek
    Samantha M.

    I had my wedding here in April 2012, and I couldn't have asked for a more perfect weekend. My husband and I still receive compliments from our guests over a year later and how it was one of the best weddings they have ever gone too. Our Wedding was a Saturday and so our guests got to stay Friday and Saturday night; it was so wonderful to have the place to just our family and friends, it made the whole weekend feel so intimate. We were lucky to have our wedding rehearsal that Friday night, all our guests loved it, the food was amazing and the staff was great. We had such a pleasant experience with all the staff that worked at the wedding, my husband and I as well as our parents received the VIP treatment during the wedding as we had our own very attendant to make sure we had everything we needed during the event. One review complained about it not being a great place for an outdoor wedding and I couldn't disagree more. Our wedding day was severely overcast and had a 50% chance of rain (what would you expect in Maryland in April) and our wedding coordinator had us make the call on what we wanted to do 3 hours before the ceremony; they did have a covered dock as well as tent on an upper level that you could choose from for the ceremony in addition to the ballroom that the reception would be held. One of the reasons we went with The Oaks was due to the several options we had in case it did rain. After the wedding I've been asked by several people that if I could change anything would I? The answer not one thing! Everything went exactly how my husband and I wanted it to go and it will be one the best weekends of our lives and that was all due to the wonderful staff and management at The Oaks!!!

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    Beautiful dining room, great food and wine and attentive service. Will most definitely return soon.

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    Ask the Community - The Oaks Waterfront Hotel

    Review Highlights - The Oaks Waterfront Hotel

    My son and new daughter-in-law were the first wedding at the newly refurbished Oaks Waterfront Inn.

    Mentioned in 2 reviews

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    Osprey Point Retreat and Conference Center

    Osprey Point Retreat and Conference Center

    4.5
    (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

    5.0
    (6 reviews)

    A fantastic place to stay! Everything was tidy, comfortable and the lake is beautiful. I enjoyed my…read moretime with friends here and would recommend it to anyone in a heartbeat.

    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!

    The Willow Grande

    The Willow Grande

    3.7
    (3 reviews)

    I had a very similar experience to the bride from June 2012. My wedding was September 2011, however…read morewe purchased the $10,000 package. We, too, shared our dissatisfaction with the owner, without receiving any remorse. We wanted to share our wedding with our entire family, including children, so we requested chicken nuggets to be included. Chicken nuggets were never provided, and the owner seemed surprised that we wanted chicken nuggets when we asked for the status of them.The food that was served was ok, but our cake appeared almost homemade. None of the staff assisted with cutting our cake either. Our flowers were very underwhelming, despite sending several pictures of exactly what I wanted for the bouquets and center pieces. The bouquets used a plastic holder rather than binding and kept falling apart throughout the evening. The photographer was fantastic, but he never got any of the information we emailed the owner to send to him, including a list of requested photo shots and a list of wedding party/immediate family. The owner also charged us double his normal rates! We are keeping in touch with him and will be using his services again, at his reasonable rates. Our officiant was very magical; we were very pleased with her. We plan to reach out to her for future functions. Rent the venue, it is beautiful. Do not buy a package! You will be a happier bride if you coordinate yourself, or hire an outside coordinator. The owner will promise a free night stay on your anniversary... we've been married a year now and didn't even get an email returned.

    This little destination event spot will be deeply missed. I attended several weddings here, each…read moreso charming and unique and Etsy-like. Such thought and love was present. And each time, there was a different style of catering and overall theme that was spread across the whole property. And that view!! What a shame they closed their doors. It was like stepping back in time. Onto a giant Pinterest board.

    Chesapeake Bay Maritime Museum

    Chesapeake Bay Maritime Museum

    4.5
    (61 reviews)

    When I started planning my very first trip to St. Michaels, there was one attraction that made the…read moreitinerary before almost anything else: the Chesapeake Bay Maritime Museum. I'd heard so many people rave about it that I figured it deserved a few hours of my vacation. Turns out...a few hours wasn't nearly enough! Admission was $22 for adults, and one of my favorite surprises was learning that your ticket is good for two consecutive days. A volunteer at the front desk gave me a wonderful overview of the property, explained how everything worked and made sure I knew I was welcome to come back the following day as long as I didn't lose my admission sticker. That's tremendous value for everything there is to see! The first thing I realized after walking through the doors? This isn't just a museum. It's an entire waterfront campus! The Chesapeake Bay Maritime Museum sits right on the Miles River and includes historic buildings, floating vessels, exhibitions, gardens, a working shipyard where traditional wooden boats are still restored and built, and enough history to keep you wandering for hours. Whether you're interested in Chesapeake Bay history, boats, lighthouses, watermen or simply beautiful places to explore, there's something here for just about everyone. Now...in true to me fashion...I headed straight for the gift shop before I looked at anything else. My philosophy is simple: shop first, think about it while I explore, and if I still love it by the time I leave, I already own it. Except...that didn't exactly happen this time. I found something I loved immediately, bought it right away and happily carried my purchase around the museum for the rest of my visit. RELATED SIDEQUEST & PRO TIP: While I was wandering through the gift shop, I overheard another visitor asking an employee if they sold U.S. Lighthouse Society Lighthouse Passport books. Wait...what passport?! Excuse me while I casually eavesdrop. A very quick Google search later, I had fallen headfirst into yet another travel rabbit hole. Apparently there's an entire Lighthouse Passport Program where visitors collect official lighthouse stamps from locations all over the country. Well...that sounds dangerously like something I would absolutely obsess over! The museum has an official lighthouse stamp available at the front desk, so even though I don't own the passport yet, I stamped a blank piece of paper to tuck safely away until I order one. I have a sneaking suspicion I'll be back to stamp the real thing someday! PRO TIP: Get your lighthouse passport before you go! I spent the next several hours wandering the campus completely at my own pace. One thing I really appreciated was that the museum lets you create your own experience. Some exhibits fascinated me, others I breezed through, and there was never any pressure to see things in a particular order. It felt more like exploring than touring. The museum itself was fantastic and easily worth the $22 admission. More than anything, I came away impressed by how much pride everyone there takes in preserving and sharing the history of the Chesapeake Bay. It's clear this isn't simply a collection of artifacts. It's a place that's actively keeping an important part of Maryland's history alive. Whether you're visiting St. Michaels for a weekend or just passing , I'd absolutely recommend making time for the Chesapeake Bay Maritime Museum. And while you're there...don't forget to get your lighthouse passport stamp!

    This is a lovely museum. The exhibita are well done. They have numerous buildings to explore with…read moredifferent parts of maritime history. We used the overnight docking facilities which come with electricity and showed and bathroom. We had a great time.

    Tidewater Inn

    Tidewater Inn

    3.5
    (126 reviews)
    $$$

    This is our first time in Easton, MD. Tidewater Inn is at the heart of the city. Perfect location…read moreto stay and explore Easton. We came right before Christmas. It's clean, the staff are welcoming. Rooms are clean. Just a couple of things - the glass on top of the bed side table had really pointed corners, my little toddler ran into couple of times and I did also. Definitely Not very safe for children. Bathroom sliding door had us laughing. You can see and hear it all.. you really gotta love the person staying with you cause it's gonna get next level intimate lol.. Convenient and cute.. not sure if I'll stay here again though.

    What a fabulous surprise! I was in the area and wanted to grab breakfast. I checked the menu and…read moresaw something that had been a mystery for many years. Scrapple. I have never ventured to try it and I have always assumed that it was undigestible and disgusting. But I decided that if it's on the menu at this swaggy establishment that I may as well give it a try. I went for the eggs with scrape. I never expected it to come out so fancy. It was cooked to perfection and the eggs were the perfect cook for such an adventure to my tastebuds. It had a fresh bed of greens that we're drizzled with a vinegarette. Everything was delicious and the staff was amazing. I actually dropped my wallet and couldn't find it for one day and when I called they said it was in the manager's office. Kudos to an amazing staff and establishment. I found out upon retreaving my wallet that they have a great HH and that on the first Friday, it's a special hh so I will be back!

    The Oaks Waterfront Hotel - hotels - Updated August 2026

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