All Hotels by Fairmont in Winchester - 2026 Updated Prices

Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

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Our top choices for Winchester Fairmont

Fairmont Copley Plaza, Boston

Back Bay

Ximena

includes taxes & fees

28 Jun - 29 Jun

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Top Winchester Hotel Reviews

Harborside Inn Of Boston

8/10 Good

"The highlight of this hotel is its location which is very central for the lovely Quincy Market area. The staff were very friendly and nice. However the one negative for me is that there are no tea or coffee making facilities in the room even on request and none in the lobby. I have never stayed in a hotel without this facility so hadn’t thought to check. It makes a big difference to me to have a cuppa in the morning then at night so I’d need to bring a kettle for my next stay here. Otherwise this hotel is perfect !"

citizenM Boston Back Bay

8/10 Good

"Self service check in, impersonal. Not my preference, but ok if you don’t mind technology. Don’t expect a valet or concierge. The rooms also require the use of an iPad which controls the lights, blinds,tv, air as well as asking for your room to be made up( they do t do it if you don’t ask). The rooms are tiny, like cruise ship tiny. The staff at the bar was friendly and willing to answer any questions. Location is great if you’re going to Fenway or love to shop."