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    Chestnut Hill Bed & Breakfast

    4.5 (2 reviews)

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    Inn at Diamond Cove - Island

    Inn at Diamond Cove

    (31 reviews)

    $$$$

    I've always been an "old soul" in some cases. When I lived in Boston during my college years, I…read morewould feel the need to escape to serenity by myself. Sometimes I'd drive to Vermont, sometimes Maine, sometimes New Hampshire or the rural parts of Massachusetts. When I do choose Maine, I would choose this place to come to. It's very quiet and peaceful, especially during the Fall when all the kids are back in school. This Inn may be a bit too "quiet" or too "old fashioned" for some, but I love it and it gives me time to reflect, do some hiking, sit on the porch of my suite and read, do some minor cooking inside, go to the pool, or enjoy a meal or two at the restaurant onsite. The service here is impeccable every time. I love how there's always someone ready to pick me up from the ferry with a golf cart and driving through this beautiful, scenic oasis, away from the hustle and bustle of Portland or any major city, for that matter. I came back to this piece of heaven this past October and I was not disappointed. Years later, and it's still a sanctuary for me to escape to.

    Beautiful Inn, but not a lot to do. They don't offer room service, no golf and while they have a…read moregym it is not fully equipped. The staff are mostly very young but they are helpful but it feels like nobody is in charge. The pool is fine but not for these rates, the hot tub jets mostly don't work and the tub is not hot. The restaurant in the inn is nit great either. The rooms are well appointed and clean but they don't clean them unless you request.

    The Press Hotel, Autograph Collection - Beautiful decor throughout.

    The Press Hotel, Autograph Collection

    (185 reviews)

    $$$

    Old Port

    This is a very interesting hotel as it once was the printing house in portland maine. It housed…read moreradio shows and newspapers printing companies. It is located near many cute stores, coffee shops and restaurants. My room was fine nothing special about it though it did have a Nespresso machine. The bathroom was very large and the shower head is an over head one. Which is also great. I was only here for a short time but I walked around and saw they have a very nice and good size gym and meeting rooms. The people I interacted with here were for the most part nice. I would stay here again.

    I've stayed here a handful of times now. The rooms are small for the price but I'll never stray…read morefrom staying here when in Portland. They also used to provide shuttle service to/from the airport but that's not available anymore. The Union restaurant being part of the hotel is a huge plus- absolutely amazing restaurant that deserves a high praise review of its own. Morning coffee is free but you can also buy iced coffee and little breakfast items, like scones, from the lobby bar. The rooms are clean and there wasn't any disturbing sounds from neighbors. The only complaint would be that it's a challenge to get the temperature right - both on the faucet and shower. First world problems but cmon- this isn't what I'd expect from a highly rated hotel. Water is $6 per bottle if you get it in the room. So if you want to save there, go downstairs for free bottles and you can refill them near the lobby bathroom. Dogs are welcome! Nothing else to complain of- which is unusual for me, given how often I'm in a hotel (work trip on a monthly basis). That says a lot!

    Canopy by Hilton Portland Waterfront - Guest room

    Canopy by Hilton Portland Waterfront

    (83 reviews)

    Old Port

    I loved everything about our experience here. The rooms were great, the entire hotel was very clean…read morebut the staff made our stay fabulous!!! Ellis was PHENOMENAL! So kind and caring and truly passionate about ensuring we had a great time as Portland guests. Love it! and WE LOVE ELLIS!!!!

    We recently stayed at the Canopy by Hilton Portland Waterfront and came away with a solid overall…read moreexperience, though it wasn't quite perfect. The clear standout was the bed -- easily one of the most comfortable hotel beds we've slept in recently. Great mattress, supportive yet plush, with high-quality linens that made for genuinely restful nights. That alone earns the hotel strong marks. The room itself was clean and functional, but the finishes felt more mid-tier than upscale. Even as a Hilton Diamond member who received a room upgrade, the views were still pretty ordinary and not particularly scenic. The hotel just doesn't seem to deliver strong views from the guest rooms. The main area where it fell short was value. The base rate already felt on the higher side, and then parking and breakfast were both extra charges that added up quickly. Those additional costs made the total feel a bit steep for what the room delivered. That said, the location is convenient for exploring Portland's waterfront and Old Port area, and the comfortable bed went a long way toward making the stay enjoyable. If you're someone who prioritizes sleep and can find a good rate (or don't mind paying for parking and breakfast separately), this is a perfectly good option. We'd consider staying here again, especially if the rate was a bit more competitive. 4 stars -- great bed and convenient location, with some value and finish caveats.

    The Inn On Peaks Island - Great view

    The Inn On Peaks Island

    (112 reviews)

    $$

    The Inn on Peaks Island -- Great Food After Surviving the Ferry!…read more We decided to take the ferry to Peaks Island--and yes, we drove our car right onto the boat. Let me tell you, they packed those vehicles in so tightly that I'm pretty sure our car made new friends on both sides! Once the ferry started rocking, my wife completely lost her mind. She was holding on for dear life, saying she was going to be sick and that the minute we got back to the Airbnb, she was going straight to bed. Meanwhile, I was pretending to be calm while secretly checking whether our vehicle came equipped with life jackets. Thankfully, the ride was only about 15 minutes, and once we arrived, Peaks Island was absolutely beautiful. The island is so small that we drove around the whole thing in about 15 minutes. Most visitors were cruising around in golf carts, while we showed up in our full-size vehicle looking like we were relocating permanently! The island has charming homes, gorgeous waterfront views, a cute little fire station, tiny shops and probably the most adorable post office I have ever seen. Everything looked peaceful, clean and picture-perfect. Even the local restaurant named Cockeyed Gull had us laughing before we ever walked inside anywhere. You know you are on a special island when even the seagulls have personality! Then we found The Inn on Peaks Island, and it was the perfect place to stop and eat. The outdoor seating had a relaxed, tropical atmosphere with a little Jamaican-island vibe--Maine seafood mixed with "don't worry, be happy." We got a little rain while sitting outside, but nobody cared. After surviving the ferry ride and my wife's dramatic farewell speech, a few raindrops were nothing! We ordered enough food to perform a full restaurant inspection: clam chowder, beef chili, lobster rolls, a hamburger, cheesesteak and Bang Bang shrimp. Everybody sampled everybody else's plate because apparently ordering your own food means absolutely nothing in our family. The clam chowder was creamy and loaded, the chili was hearty, the lobster roll was fresh and packed with lobster, and everything else disappeared faster than my wife trying to get off that ferry! The food was delicious, the atmosphere was relaxing and the entire Peaks Island experience was unforgettable. Definitely visit The Inn on Peaks Island--just arrive hungry, bring your sense of adventure and make sure whoever is riding the ferry with you has a strong stomach!

    Over priced and mediocre food with small portions. The fries are frozen. The fish taco tortilla was…read morehard, the fish was dry, and the minuscule amount of slaw was sweet. No fresh salsa or pico de gallo in sight. The salad dressing was just oil. No vinegar. The clam chowder was gelatinous. It's clear they don't care about the food they serve at all. You are better off eating in Portland. Don't waste your money here.

    Chestnut Hill Bed & Breakfast - hotels - Updated August 2026

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