The red brick facade of the Four Seasons is the kind of building you probably imagine when thinking of Boston. The building was once the city’s Playboy Club and is found among Victorian brownstone buildings. Once inside it’s unashamedly fancy, with chandeliers, marble, plush bespoke textiles and abundant space and light. Guests can dine in the Aujourd Hui Lounge, the Sottovento Coffe Bar, outdoors at The Sanctuary or poolside. Rooms range from deluxe kings to speciality suites offering separate living and sleeping areas (perfect for extended stays). Accessible rooms across each of the categories are also available to book. The indoor pool has a great view and there’s a gym for those wishing to work out.