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Winter Hill Vacations from $617

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The Latest Winter Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar
    Aug 27 - Aug 29

    Boston Harbor Hotel + Flight

    North End
    2 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Great location and very helpful staff"
    Reviewed July 16, 2026
    Roundtrip • Atlanta (ATL) - Boston (BOS)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    Save 100% on your flight
    $995
    $617
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Coffee/tea maker, full-size fridge, microwave, oven
    Oct 2 - Oct 6

    Boston Lodge and Suites + Flight

    Dorchester
    4 nights
    4.0 star property
    8.4/10 - Very Good (190 reviews)
    "Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles."
    Reviewed May 19, 2026
    Roundtrip • Atlanta (ATL) - Boston (BOS)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,454
    $729
    per traveler
    found 1 day ago
    Boston Lodge and Suites
  • Terrace/patio
    Sep 30 - Oct 3

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (474 reviews)
    "perfecto"
    Reviewed June 8, 2026
    Roundtrip • Atlanta (ATL) - Boston (BOS)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    Save 100% on your flight
    $2,531
    $1,514
    per traveler
    found 1 day ago
    Four Seasons Hotel Boston
  • Apartment | Interior
    Oct 3 - Oct 8

    Furnished Apartment Near Longwood + Flight

    North Brookline
    5 nights
    3.0 star property
    6.8/10 - (5 reviews)
    "This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells. Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not..."
    Reviewed July 6, 2026
    Roundtrip • Atlanta (ATL) - Boston (BOS)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    Save 100% on your flight
    $1,459
    $920
    per traveler
    found 1 day ago
    Furnished Apartment Near Longwood
  • Family Apartment, Kitchen, City View | Living room | 30-inch LCD TV with digital channels
    Sep 10 - Sep 13

    Market Square Inn + Flight

    Downtown
    3 nights
    2.0 star property
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DAL - BOS • 1 stop BOS - DFW • 1 stop
    Save 100% on your flight
    $5,598
    $3,699
    per traveler
    found 20 hours ago
    Market Square Inn

What to do near Winter Hill

Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$47
per adult
80% of travelers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities near Winter Hill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.