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    Nichols House

    5.0 (3 reviews)

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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!!

    Wylder Hotel - Tilghman Island

    Wylder Hotel - Tilghman Island

    (47 reviews)

    $$$

    I'm so late in posting this review and was reminded to do so when I went to look into booking…read moreanother stay with my family for this summer. In October, I stayed in the Wylder Hotel for a quick weekend away. It was my first time and I have to say it was the most relaxing and peaceful trip. The hotel's property is spacious and beautiful with a stunning view of the water. There are fire pits around the property to gather around, have a drink, roast marshmallows or just watch the sun go down. There is also a restaurant attached to the hotel which was perfect for having drinks and dinner at for a resort kind of vibe. The sauna on the property with a cold water plunge was incredible! You can sign up at the front desk for your session. The pool is another amazing amenity on the property to add to relaxation and fun. In the morning, there is a continental breakfast prepared. You are able to take your coffee and/ breakfast to any of the seating options. I found some really comfortable couches outside that were perfect to wake up to. They supply a bunch of community games as well. The room I stayed in was was on the smaller side. However, it didn't impact my stay. The bed was comfortable! The room was clean. The staff were extremely helpful and friendly. Like I said, I'm making another trip back but this time with my family and I can't wait to show them around and have a fun and peaceful weekend with them as well.

    Nice throwback kind of hotel on the island. Great people and service all over that I met from the…read morehotel, and location sits right off the bay which is pretty cool. Very relaxing location with fire pit at night and other activities available as well. The food was pretty decent and very reasonably priced and the live acts they had on site were both really good and added to the relaxing feel of the hotel. Just make sure you are familiar with the town for when you come as it is more of a sleepy like country town, where a good amount of the restaurants and stores do close early. But the little country store up the road is really good at having just about anything you may need including adult beverages. It is an older establishment though, so no elevator and I found you may have to wait on hot water at times especially if filing the tub with water jets. A nice fridge also in the room but no microwave which would have been nice seeing how the restaurants provide such large portions around town. We had the King waterfront suite, so maybe the bungalows have microwaves.

    The Wildset Hotel - Wildset Hotel, St Michaels Md

    The Wildset Hotel

    (23 reviews)

    Staying at The Wildset Hotel for one night visiting from Washington, D.C., I enjoyed the overall…read moreexperience. It's inside three historic buildings along the main street near the very posh Inn at Perry Cabin. The main building used to be a schoolhouse. Here's my overnight experience. 1) Check-In: The hotel communicated with me via text with clear instructions on how to check-in. I parked in the main building's lot and checked in inside their cafe/shop. My room with a king-sized bed was in The Brick House across the street from the main building. Even with a short line, I was in my room within minutes. 2) Rooms: My room came with a shared balcony overlooking the main street, a little fireplace, a comfy king-sized bed, good shower water pressure, towels, an iron and board, a TV, and free water and chips. The minimalist farmhouse look plays well inside the room. There are plenty of outlets and a shelf for my belongings. Two books came in the room for light reading. 3) Space: The main building has a little shop with local products, snacks, and more. There's also a coffee shop and their restaurant- Ruse. 4) Amenities: Each building has a free parking lot for guests. Breakfast is included each morning as are snacks in the room. Every evening, you can pick up a free s'more kit and roast marshmallows in the back firepit. The hotel offers free yard games and bikes for guests to use. 5) Service: The woman behind the front desk was friendly and helpful! Other reviews noted this, but the walls are thin. I could hear everything the guests next door to me were saying and doing- doors slamming, talking, everything.

    The Wildset is a fine, central option when staying in St. Michael's. It's minimalist-chic with a…read moresort of rustic feel as well. Some of the staff are friendly, some are not. The main building is cute, with a lovely sundry shop and the hotel's restaurant, Ruse. We stayed in the building across the street. The room was fine, albeit small. I think I was expecting it to be more luxe. I really enjoyed the shower and the fireplace, which they had just turned on for the season. We noticed the vents were dirty and the filters needed cleaning, so even though everything else appeared clean, who knows what else they are missing. The bed and pillows were soft and comfortable. I appreciated the snacks and water. There was no sound proofing in the building, as I could hear doors slamming and conversations all night. And, a staff member walked into our room as we were getting settled. I definitely used my door jammer/alarm that night, because that was not good. The door didn't have an internal latch, peep hole, or do not disturb sign. However, this building was only accessible by keycard, which was good. Breakfast is included. There are pastry, granola, and yogurt options, plus coffee (they use Ceremony) and juice. I loved the savory biscuit, but get there early for that. I'd return, though I'd book a better room class than standard king, and perhaps that would improve my experience. However, my partner would not return. I hope they act upon their areas of improvement.

    Nichols House - hotels - Updated June 2026

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