Massachusetts

Boston: Five Nights, Four Hotels

Five nights in and around Boston with a different neighborhood most nights: Beacon Hill, the harbor in Everett, Harvard Square and the Financial District, each stay with breakfast for two and a late check-out attached.

Nights5
SeasonSummer
StyleBoutique and luxury
PaceRelaxed
SuitsA couple
Based onA trip I took myself

Where to stay, and why

XV Beacon

Beacon Hill, Boston · 1 night

A small hotel on Beacon Hill, 63 rooms by its own count, steps from the State House, Boston Common and the Public Garden, so the first evening needs no transport at all. A Classic Queen, with breakfast for two, a dining credit, early check-in when a room is ready, an upgrade when one is free and a guaranteed late check-out. The plan for the credit was dinner at Mooo, the steakhouse in the building.

Encore Boston Harbor

Everett · 1 night

A resort night outside the city, on the Mystic River with the Boston skyline across the water, a spa and the Harborwalk gardens. The rate came with a spa credit, breakfast for two, early check-in, late check-out and an upgrade when one is free.

The Charles Hotel

Harvard Square, Cambridge · 1 night

Harvard Square, across the river in Cambridge, at an independent hotel I also suggest to families visiting Harvard and the other Boston campuses. A Deluxe King, with breakfast for two, early check-in when a room is ready, an upgrade when one is free and a guaranteed late check-out.

The Langham, Boston

Financial District, Boston · 2 nights

The former Federal Reserve Bank on Post Office Square, now a recently restored hotel, within walking reach of Faneuil Hall, the Freedom Trail and the harbor waterfront. Breakfast for two, a dining credit, early check-in, late check-out and an upgrade when one is free.

Day by day

  1. Day 1

    Beacon Hill

    Fly in and check in at XV Beacon, with dinner planned at Mooo, in the hotel, on the dining credit.

  2. Day 2

    Beacon Hill to Everett

    Beacon Hill and the first part of the Freedom Trail with self-guided audio tours: the State House, Acorn Street and Louisburg Square, then the Common, King's Chapel, the Old State House and Faneuil Hall. Lunch around Faneuil Hall and Quincy Market, then out to Encore Boston Harbor for the night.

  3. Day 3

    Harvard Square

    Across to Cambridge and The Charles Hotel. A late check-out at one hotel and early check-in at the next keeps a one-night move from eating the day.

  4. Days 4 and 5

    Financial District

    Two nights at The Langham on Post Office Square, a short walk from Faneuil Hall, the North End and the waterfront.

  5. Day 6

    Boston

    The flight home.

What made it work

  • A different neighborhood most nights, so each day starts somewhere new instead of with a commute back into the center.
  • Early check-in when a room was ready and a late check-out on every reservation, which is what makes one night per hotel work: the move happens in the middle of the day, without waiting in a lobby with bags.
  • Breakfast for two at every stay, and a dining or spa credit on four of the five reservations.
  • The two nights at The Langham were booked as two one-night stays, and each came with its own breakfast and dining credit.
  • The first full day on foot with a self-guided audio tour of Beacon Hill and the Freedom Trail, from a hotel that sits at the start of both.