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    Shining Sails

    4.0 (8 reviews)

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    View from our deck
    S M.

    We decided to take a last minute trip to monhegan for one night and we were lucky enough to snag an apartment at fish and Maine inn. We stayed in the periwinkle. It was amazing. The location couldn't have been better! We had so much fun there. The WiFi worked perfect and the place was clean and accommodating. The ONLY thing I can say is if you are going to do some cooking bring your own oil/butter but if you forget, like we did, you can buy it just steps away from your door at the grocery store. We loved this place and this island! We will definitely be back!

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    John Sterling Harbor House - John Sterling

    John Sterling Harbor House

    5.0(2 reviews)
    0.1 mi

    Vivian did it again. Another great island adventure. This one on Monhegan. The John Sterling…read moreHarbor House was our base of operations. This is an ideal spot. It's just up from the ferry dock. Breakfast is fresh every morning. Your right at the center of island life with out it being on top of you. The microwave and fridge give you the option to eat on the cheep. However the temptation of the food at The Island Inn just across the road may be hard to resist. The Sterling house puts you at the center of the Island and its history. It is still owned by the original family going back eight generations. Tranquil down east views are out every window. What a great fined.

    Love: the pair of Adirondack chairs to behold the priceless views of the sea at sunset…read more Bonus: homemade, freshly baked, warm blueberry muffins every morning. My husband and I stayed with our cocker-spaniel this June (2017) at the JSH Inn. We got along very well with Susan, who is funny and amiable - she even offered to pet sit our dog so we could have an elegant dinner right across the road at The Island Inn! She was an amazing host. Maybe next time we will get to meet her husband Mark. The JSH inn is very conveniently located both to the harbor and to Main St on Monhegan Island. The almost 300-year-old inn was gut renovated in 2005. It is neat and tidy, authentic in design, pro-conservation and cheerful. Susan was incredibly hospitable and helpful, as her knowledge comes from generations of living on the island (during the warm part of the year). In the rooms, you will find authentic touches including old photos of the inn and windows dressed with charming lace curtains. Be on the lookout for small thoughtful luxuries, including a tiny dish of chocolate kisses and a vase of freshly cut purple lupines. I would recommend this inn for couples, singles, and families of a gentle and polite disposition. I'll be back!

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    John Sterling Harbor House - Quadcentennial Banner beckons our return

    Quadcentennial Banner beckons our return

    John Sterling Harbor House - Plan your Monhegan adventure over a hot and healthy breakfast

    Plan your Monhegan adventure over a hot and healthy breakfast

    John Sterling Harbor House - Perriwinkle Room with a direct harbor view

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    Perriwinkle Room with a direct harbor view

    Topside Inn - Coastal Bliss

    Topside Inn

    4.8(72 reviews)
    16.6 mi

    Incredible. Topside was an amazing stay and experience for us. We booked room 14 which was the…read morecorner top floor building. It's the best ocean view, very private, quiet, and picturesque. The room itself has a view of the harbor with large picture windows, and the bed is very comfy, best we slept all trip. The amenities provide anything you need and they are all clean non toxic products for shampoo, lotions etc. We were greeted in our room with roses, a hand written note, and chocolates which was such the added touch. The private lawn has chairs to enjoy the view, and games like cornhole. Yes, the breakfast is wow! Homeade and tailored for any dietary need as well, so very thoughtful. They provide snacks and drinks all day. Staff is wonderful, and we couldn't have asked for anything better. This is worth your stay! We will be back!

    This is a review I don't want to write…read more Our 12-day road trip in honor of our being married 20 years was an incredible experience, which we shall cherish for the rest of our days. As much difficulty as I had planning it (for a variety of reasons I won't bore you with), everything ended up turning out GREAT. Ironically, though, the one place I was MOST excited to experience... Topside Inn... turned out to be our least favorite, and that makes me sad and even a little angry, and that's why I don't want to write the review. I've written many a negative review if a place warrants it, but this one still bothers me. It wasn't that it was horrible. No. In fact, I would probably say that our stay was even "decent" overall, but there were some annoyances and disappointments. I'll start with the disappointment. We stayed at this inn during our actual anniversary. The person assisting my travel agent friend who booked it said how excited they were at the inn. Here's the irony... not only did they do NOTHING for it, they couldn't even muster saying "oh, we heard it was your anniversary. Happy anniversary." NOTHING. Not one word. Not one gesture. Did I need them to do something? No. We had our own celebration, but at every other place we stayed for our 12-day trip, the other places somehow acknowledged our anniversary with kind words and/or some gesture... like a little box of chocolates or a 1/2 split of sparkling wine/champagne. Something. Did I expect anything? Not at all... but again, when the reservationist made an initial fuss over our anniversary being at THEIR place and how exciting it was, yeah, I expected at least a greeting. Now for the annoyances. I have a bad back and bad knee. The reservationist was given a full explanation of what our room needs would be. No stairs, easy access, difficulty with uneven ground, and they assured my travel agent friend they had the perfect room for us. They said the room would be on the ground level with no stairs involved. The problem is that they did not pay attention because I ended up dealing with very uneven ground walking up and down a gravel incline, along with a few stairs to boot, and they could have given us a room on the same level as the parking lot where we'd only have to wheel our suitcases a few feet to the room without any stairs, gravel or inclines. In a few words, they BLEW IT. It wasn't easy for me to deal with the slippery gravel, not to mention the incline and the few stairs, but I dealt with it. I just know it could've been MUCH EASIER if THEY had paid attention. I had never been to their property before, so I would have no way to know how things were laid out or what room would suit me best... but they did. The room itself was clean and SOMEWHAT comfortable. I say only somewhat because the mattress, at least in the room we stayed in, was very weird. The sides of the mattress severely sloped downward, so that when I would sit on it or even lay, I felt like I would roll right off... esp. on the side of the bed where I slept. This was an issue throughout our stay, and it definitely posed a challenge to deal with it. Another issue I had with the room was that the shower was small, but worse than that, it was incredibly slippery. I was terrified I was going to fall because there was nothing to hold onto; nor was their any non-slip mat or strips. People rave about the breakfasts served here. I was expecting some incredible elaborate feast, based on what we read and were told. However, I was completely underwhelmed with the breakfast when we were there. Basically, we were given scrambled eggs and sausage, neither of which was anything special in taste or presentation. There was some kind of strawberry sauce over a biscuit, and while it looked pretty, it had no flavor. I'm not a cereal eater, so I didn't have any. I don't know... it was a big miss to me. I just didn't see or taste why people think this is so wonderful. It completely eluded me. We paid a lot of money to stay here. It should've been a lot better for what we paid, and by the way, we paid less everywhere else and got much better service, much better comfort, and we were treated better by any of the other places we stayed at. There are enough other choices in this town that if we ever return, it won't be to this establishment. Again, it wasn't bad... it just wasn't great either.

    Photos
    Topside Inn
    Topside Inn
    Topside Inn - "Above it All" in the center of Boothbay Harbor

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    "Above it All" in the center of Boothbay Harbor

    Shining Sails - bedbreakfast - Updated August 2026

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