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    The Wayside Inn

    3.9 (20 reviews)
    Open • Open 24 hours

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    Beautiful furnishings
    Bill S.

    The highlight of our trip! A few things I must point out, the Yelp description for The Wayside Inn is now under new ownership. Susan & David are no longer the propitiators. I met the owner, an unassuming man in the kitchen and shook his hand when I left. Joe is the manager and greeted us when we arrived on Saturday. I told him we have dinner and concert plans and would be back late. He gave us a through tour on how to use the fancy coffee maker, how to use the jacuzzi tub (we didn't us it) as well as the robes. What struck me the most was the branding. The robes as well as the beautiful coffee mugs all had a wonderful logo. Once we took our belongings out and settled into the room, we decided to enjoy the outdoors. My wife grabbed a beautiful blanket and we went outside on the roof deck. We're just taking it all in, I had a bottle of Napa Valley wine I brought from home for us to enjoy, it was really picture perfect. The actual inn is over 200 years old, one of the historic homes in Maryland now made for my enjoyment. Did General Washington sleep here? Inquiring minds want to know! The staircase was truly a sight to see. Made from wood, they crafted these beautiful wooden turns to the upstairs. Creaky wood? Sure. It gives the inn a comfortable charm. Our bedroom had a magnificent sleigh bed and the sheets? Joe was explaining to my wife the thread count. I'm a guy, I was tuning it all out, haha! After a comfortable night sleep, I woke up early. I'm an early riser, I made myself a great cup of coffee and went downstairs to read my book. The sitting area with it's beautiful furnishings, it's a welcoming room. Everything is meticulously cared for, it was a pleasure to have this moment alone and take it all in. After an hour, I went upstairs and took a shower. We have 8:30am breakfast reservations, I want to get on the road to beat the traffic. We were served a French toast bake, absolutely divine. When staying at any B&B, the shower products as well as the food should be top notch. Staying at the local Marriott doesn't give you the same experience. After breakfast my wife made us Dove Hot Chocolates as we packed up. I highly recommend The Wayside Inn. From the quaint accommodations to the fab breakfast, I thank you making our stay special.

    susan m.

    We stayed here to see a concert at the Merriweather and it was a delight. We were welcomed with a bottle of wine, champagne and fruit plate when we checked in. It was quiet and lovely. We certainly will stay here again.

    Orange Cranberry Strata
    Al D.

    I cannot, cannot believe there are no reviews of this amazing inn yet. Brace yourself for a long review because I want to cover everything so people know exactly what to expect (which is all good things). The Wayside Inn is a gorgeous place to be - I almost hesitate to call it merely a "bed & breakfast" because it's so much more than that. The meticulous details with every aspect of the inn is almost like a dream - everything is perfect, right down to the sign post that marks the driveway along the road. My boyfriend & I arrived between 4 PM and 5 PM on a Friday - actually on the eve of the east coast's "storm of the century" (I say this sarcastically) hurricane Irene. The outside is like a story book home - it looks nothing like the modern houses down the road. It's a 17th century brick home with an adorable outside awning. They seem to have two add-ons which do not stand out too much, one of which is their adorable "sun room." Inside, we met David, one of the two innkeepers. He is a very vibrant, considerate host, and were grateful for how down to earth he was. We stayed in the Banneker Room - and we are so glad we chose this room out of the many choices. It definitely was the best selection, being just the right size for two people who want to get away. My boyfriend surprised me by requesting sunflowers in the room - a request David was able to fulfill. Thank you so much! The bed was humongous - and very high, too! They provide a step-stool to get up top (if you are short, like me). Once on top, it's a sea of pillows. The bed spread matched the color scheme of the room - blue, golden yellow and green. There was a giant, extremely cozy comforter at the edge of the bed. Underneath, the sheets were very, very soft and light. The bed was great for lounging on while watching the TV - which was a flatscreen that included FIOS cable, so of course we had more channels than one could possibly imagine. There is no DVD/VCR player in the Banneker room but we noticed outside the room there was a selection of things to watch - so some rooms probably provide players. Of course, my boyfriend brought the right wires to connect his computer to the TV, so we had no issue watching a movie as the hurricane's storms passed by. The bathroom is a luxury unto itself. I've seen other hotel rooms merely the size of the bathroom. There is both a stand up shower (with a build in bench) and rainforest shower head, and - best of all, a jacuzzi/jet tub. We brought our own bubble bath bomb, but there was bubble bath soap provided in the room. This bath is worth the trip alone, really an amazing way to spend time on a rainy day. Outside our room, on the second floor, is this amazing custom-coffee machine. These are those new machines I've been seeing often, where you place the pouch of your choice in the machine. They kept some of their custom made mugs nearby for a quick coffee. There was so much variety, from espresso, to cappuccino, to hot chocolate, and flavored coffees - all fresh, not instant. I loved this machine so much because I could grab a coffee at any time - it was right outside our room! I know I keep talking about the bed - what about the breakfast? I am not exaggerating when I say this is the best home-made breakfast I have had, ever. Breakfast was served on their gorgeous wooden table in their dining room - coffee served in their own custom made mugs, and delicious, fresh juice. There was a first course both mornings with a fresh fruit salad (all of the good fruits, too - strawberries, blueberries, peaches, grapes) - one day with yogurt and granola, the next morning the fruit was cooked in some vanilla sauce and topped with whipped cream and nutmeg. Saturday morning was this amazing orange-cranberry strata made with croissants. Incredible! The following morning it was cinnamon Irish cream challah french toast. Because we were the only patrons (the storm had scared people away) that morning we got second helpings and we couldn't help ourselves. After breakfast one morning we hung out in their quaint library, which was very, very relaxing. The room had various books and board games. My boyfriend used the free wifi while I read. In the background, you could hear a radio playing classical music. It was very peaceful to sit in this room, drinking coffee, while it rained. Checkout, also was no hassle. We took our time with no rush and left around noon. I also bought a mug and some jam they had. David was so helpful because he took my card to pay for these items, and wrapped them. He also wrapped my sunflowers in a wet paper towel & foil. We weren't sure if we'd return that night due to the storm but my boyfriend and I severely regret not turning back. I cannot, cannot recommend this inn enough - just to lounge around alone was a pleasure. The town itself was beautiful but I'd go so far as to say the time we spent here outshone everything!

    Tiffany S.

    Could not have asked for a better way to celebrate our 6th anniversary! We arrived on a Friday evening after sitting in a bit of traffic. The owner, David, has called us to check in as we were supposed to arrive a while before. He was upbeat and understanding of the traffic in that area. Upon arrival we're were greeted by him and Susan. They were happy to see us and were incredibly warm. Susan showed us to our room, pointed out the features and gave us a quick tour of the home. We had added on the romance package to our stay and everything was set up beautifully- the roses, chocolate covered strawberries, and champagne in a bucket (oh and bubble bath for our jacuzzi!). We stayed in the Banneker Room- the sheets were to die for! Breakfast each morning was lovely. Saturday we had the baked eggs with six cheeses and ham. Sunday we had the Cranberry Orange croissant soufflé with bacon. Both were preceded by a fruit and yogurt granola parfait. The staff that made the breakfast were equally as accommodating and gracious as the owners! The inn is lovely and quiet, I utilized the small library just off of the front sitting room to sip coffee and crochet. There is much historic charm, not to be over shadowed by the modern conveniences. This was my husbands first stay at a B&B, but it won't be his last.

    Breakfast was delicious!
    Kiki V.

    Super comfortable bed (and sheets - you can purchase them, too!), jacuzzi tub, fireplace and flat screen HD TV. Our room had a private entrance which was great, and the breakfast and staff were incredibly wonderful. Close to downtown shopping, worth a visit!

    Lovely private bathroom in our relaxing room

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    Review Highlights - The Wayside Inn

    “Susan showed us to our room, pointed out the features and gave us a quick tour of the home.”

    Mentioned in 6 reviews

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    Wilderness Bed and Breakfast

    Wilderness Bed and Breakfast

    (3 reviews)

    $

    I've stayed at numerous b&bs around North America, and The Wilderness is the second best of all the…read morebunch. Ellen is a terrific and very accommodating hostess. One of our party has celiac disease, and Ellen was gracious enough to supply not only gluten-free breakfast options, but also to bake up some gluten-free peanut butter cookies as one of her afternoon treats. Cat lovers will be pleased to make the acquaintance of the sociable household cats. People allergic to cats will be pleased to know that none of the cats are allowed into the private rooms. One of our party is allergic to cats, and had no significant trouble from cat dander. (However, pollen was plentiful in the region, so be aware of environmental problems.) My favorite part of the inn was the screened back porch, providing sunshine, fresh air, and plenty of bird watching opportunities with three separate feeders around the porch. So peaceful and pleasant! I highly recommend The Wilderness.

    My husband and I wanted a little getaway so we decided to stay at The Wilderness and it was perfect…read morefor us. Ellen sent very detailed instructions through email well before our check in time that detailed everything we needed to know. When we walked in, there were delicious homemade gluten free pecan squares waiting (Ellen asks for specific dietary restrictions when booking and she obviously takes them to heart!). The Sullivan suite is a great size with a comfy queen bed and sitting room. We loved the old furniture pieces and the overall antique feel of the whole house. Before checkout, Ellen made a wonderful homemade breakfast. It was exactly what we needed for a relaxing weekend! We will definitely keep The Wilderness in mind for future getaways.

    Aida's Victoriana Inn - Sitting room with picture windows

    Aida's Victoriana Inn

    (27 reviews)

    $$

    Stayed here for a weekend anniversary get away. Right on…read morethe inlet of the bay. Great location near all the shops and restaurants. Our room was good size, large king bed. Window of the the water with a great view from our room. Room was neat and bed was comfortable. Stayed for the weekend, breakfast both days was good. French toast, eggs and sausage morning one. Morning two eggs or pumpkin pancakes. Both were great. Only negative was the shower in our room. It was a stall shower, which we knew, but the water pressure was terrible. It also took about 10 minutes to come to a warm temp, I felt bad running the water that long. All and all great stay. I'd 100% suggest this place for a weekend getaway.

    We just returned from two nights in St. Michael's and had the pleasure of staying at Aida's…read moreVictoriana Inn. We chose a second floor room with a water view. Before we left I planned a surprise sailing cruise for my fiancé and Aida left a sweet note about the gift from me and vouchers for complimentary gelato around the corner for us. She is so accommodating even when a few little things didn't go as planned for us. (Car trouble, weather... not her doing at all but she made them easier to manage.) She has great suggestions for what to do in St. Michael's. Breakfast was set up beautifully in the morning and cooked to order. Portions were huge if you wanted them. We are lighter eaters and once I told her that she gave us perfect smaller portions, but if you want a big breakfast you will not be disappointed here. The inn only has about eight rooms, and each is different. Ours was very comfortable with flowers, art and antiques wherever I looked. There's central air and the softest towels I think I've ever used. She lets you keep stuff in the fridge and even said we could use her laundry when my fiancé sat on something and messed up his pants. We had leftovers when we needed to leave and she gave us a styrofoam cooler to take with us... that will be used a lot this summer, I'm sure. The location is walking distance to most things in town, so while there is off street parking, we walked most of the time. You can't go wrong here with Aida's Victoriana Inn! Note, though, a lot of businesses and restaurants in town are operating at partial capacity or reduced hours, or are closed due to Covid 19. This has nothing to do with the Victoriana Inn, but it is worth calling ahead if you have specific things you want to do while in town to make sure they're available. We had to shift some dining plans but it was a last minute getaway and we didn't care all that much. It a worked out but if you have your heart set on something, check in advance to make sure you'll be able to do it.

    Point Breeze Bed and Breakfast - Captains Quarters

    Point Breeze Bed and Breakfast

    (5 reviews)

    We had the pleasure to stay at this hidden gem of a B&B last weekend! I would highly recommend…read morePoint Breeze to anyone. We loved it and wished we could have stayed longer. Pros: There are many more popular B&Bs and inns in town, but Point Breeze has several perks. We felt like we had really lucked out and ended up with the best choice! 1) Lovely waterfront location with a great view of the harbor and lighthouse. Most of the B&Bs in St. Michaels are right on the main drag and not on the water. I doubt any of the other places have such a great view! 2) Kayaks, canoe, and bikes available for guest use -- no extra cost! 3) You're free to laze about anywhere on the beautifully landscaped yard. 4) You can fish from the private dock, and the innkeeper will help you "chicken neck" for crabs, if you want. 5) Joan, the innkeeper, makes a mean omelette and awesome German pancakes! 6) Speaking of Joan, she's a sweetie! So wonderful to talk to! 7) Very quiet area. Not right in town, so you don't get all the road noise. Very peaceful. 8) Free soft drinks available any time. 9) Costs quite a bit less than most other places in town. 10) Everything was spotlessly clean and comfortable. 11) Wi-Fi for all! 12) If you have a family of 6 and 2 people don't mind twin beds, you could rent the whole house out. Cons (sort of): 1) This isn't a con for me, but I can see how it could be for other people: Point Breeze's guest rooms are not fancy. You feel like you're staying over with relatives. We liked it, though! 2) No TVs in the guest rooms. A small TV is available in the great room. We really didn't care, however. We weren't there to watch TV. 3) If you don't want to take a short walk or bike ride into town, you'd be better off staying in town. We enjoyed the walk in -- not far for us at all! 4) Not many rooms -- only 3. But if you want to stay someplace quiet, this shouldn't be a problem. 5) 2 of the rooms share a bathroom. Not a big deal if you are staying with family or close friends. If you are a couple, there is one room available with a private bath. 6) Bare bones amenities in the bathroom, but more than adequate and comfortable.

    The other reviews are very accurate & to the point. Joan is an excellent host. She makes you feel…read moreat home. Excellent Breakfast both days I stayed. The home is right on the water, great sunsets & immaculate. If you have an Aunt with a house on the water stay with her. If not, stay with Joan. The house has beautiful Antiques & a quaint screened in porch where breakfast is served in season. Sailboats cruise by. The whole experience was quite delightful. A five minute drive from the heart of town, which for me was perfect. Away from the crowds and tourists.

    The Wayside Inn - hotels - Updated September 2026

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