Boston Deals

Boston Vacation Packages

 from $619
 
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.
 

Up to $100 OFF per booking with Marriott Hotels & Resorts

  • $100 OFF stays of 5 nights or more
  • $75 OFF 4-night stays
  • $50 OFF 2- and 3-night stays
  • Book by 7/22/18 for travel through 10/31/18
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Boston

  • 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.

    This hotel commands breathtaking views of Boston, and well-appointed accommodations.

    • Traditional King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $426+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 09/08/18

  • Convention Center 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.

    This upscale hotel overlooks Boston Harbor and offers glittering views of the city's skyline.

    • Traditional/1 Bed
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $489+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 08/31/18

  • Seaport Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This hotel is ideally located in the thriving Seaport District, just moments away from popular attractions and waterfront restaurants.

    • King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE

    3 nights with flight from $539+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 09/08/18

  • Copley 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.

    This urban downtown retreat is situated within walking distance of a wealth of trendy nightclubs, upscale shops, major corporations and landmark Boston attractions.

    • Traditional King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $636+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 09/08/18

US Cities and Canada - EXCLUSIVE up to $100 OFF per booking with Marriott Hotels & Resorts offer: Valid on new bookings made 6/11 - 7/22/18 for travel 6/11 - 10/31/18. Minimum 2-night hotel accommodations at participating Marriott hotel and roundtrip air required. Savings is $50 off stays of 2-3 nights, $75 off stays of 4 nights and $100 off stays of 5 nights or longer. Savings is per booking, taken at time of booking and reflected in rate shown. Certain restrictions apply.
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.]