The Windsor Inn Guesthouse
Although best known as the home of the Red Sox and Fenway Park, this area is also one of Boston’s major academic and cultural centers. Fenway and Kenmore, for instance, host Boston Latin School—the nation’s oldest public school—as well as numerous colleges and universities, accounting for nearly a dozen of the 100 higher education institutions in Greater Boston. This academic presence gives the neighborhood its vibrant energy. Undergraduates and other young locals are frequently drawn to the lively bars and clubs along Lansdowne Street.
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A lot of Fenway-Kenmore listings come furnished or move-in ready, so you do not have to buy furniture for a short stay. Use the furnished filters above, or open a listing to see what is included.
Private and shared rooms in Fenway-Kenmore cost less when you do not need a full apartment. Compare roommate counts and amenities on each listing before you message the host.
Ohana is built for month-to-month stays, not weekend trips. Set your move-in and move-out dates, then book on the platform so rent, the lease, and messaging stay in one place.