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Paul Revere's monument, Boston

Boston Vacation Packages

American history is alive and well in Boston. Massachusetts' capital was founded by the Puritans in 1630. You'll find that the city's pivotal role in the American Revolution is still palpable as you walk along its two and a half mile Freedom Trail in downtown Boston. You can almost hear the hoof beats of Paul Revere’s horse clomping down the street.

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USA & Canada - Up to $100 OFF per booking

  • Book by 09/21/25 for select travel through 12/15/25

  • Hilton Boston Logan Airport

    Hilton Boston Logan Airport

    Airport
    Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.
    With convenient access to Boston Logan Airport's terminals, this hotel is also close to downtown, museums, art galleries and much more.
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    With convenient access to Boston Logan Airport's terminals, this hotel is also close to downtown, museums, art galleries and much more.
    Book Now
  • Encore Boston Harbor

    Encore Boston Harbor

    Everett / Boston Harbor
    Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.
    This luxury resort-casino near downtown Boston offers spacious accommodations, fine dining, gaming, shopping and more.
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    This luxury resort-casino near downtown Boston offers spacious accommodations, fine dining, gaming, shopping and more.
    Book Now
  • Sheraton Boston Hotel

    Sheraton Boston Hotel

    Back Bay
    Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.
    Discover your ideal retreat here, an upscale hotel with 1,220 guestrooms, outstanding service, and an incredible location in downtown Boston.
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    Discover your ideal retreat here, an upscale hotel with 1,220 guestrooms, outstanding service, and an incredible location in downtown Boston.
    Book Now
  • The Fairmont Copley Plaza

    The Fairmont Copley Plaza

    Back Bay
    Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.
    Boston’s iconic luxury hotel blends timeless elegance with modern comfort. Steps from favorite area attractions and restaurants, it offers AAA Four-Diamond service, dining in OAK Long Bar + Kitchen, grand ballrooms, and unforgettable experiences.
    Book Now
    Boston’s iconic luxury hotel blends timeless elegance with modern comfort. Steps from favorite area attractions and restaurants, it offers AAA Four-Diamond service, dining in OAK Long Bar + Kitchen, grand ballrooms, and unforgettable experiences.
    Book Now
1-800-742-9244
  • EXCLUSIVE USA Up to $100 OFF per Booking Offer: Valid on new bookings made 07/28/2025 – 09/21/2025 for select travel 07/28/2025 – 12/15/2025. Minimum hotel accommodations at participating property and round-trip airfare required. Savings is $100 OFF accommodations of 5 nights or more, $75 OFF 4 nights, or $50 off 2-3 nights. Savings is per booking and taken at time of booking. This entire offer is based on availability and can be modified or closed out at any time.
  • Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]
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