An aerial view of a coastal area with a bridge connecting two landmasses, surrounded by dense forests and a large body of water.

Kittery Foreside Vacation Packages

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The Latest Kittery Foreside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for four.
    Dec 20 - Dec 23

    Boston Lodge and Suites + Flight

    Dorchester
    3 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • 1 stop
    CA $1,505
    CA $668
    per traveller
    found 1 hour ago
    Boston Lodge and Suites
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 31 - Feb 3

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "!"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,120
    CA $1,143
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • A courtyard with brick walls, outdoor seating, and potted plants.
    Jan 29 - Feb 1

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (497 reviews)
    "The best location and the beat service! The best swimming pool"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,360
    CA $1,513
    per traveller
    found 1 day ago
    Four Seasons Hotel Boston
  • A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
    Jan 31 - Feb 3

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,556
    CA $1,033
    per traveller
    found 1 day ago
    The Langham, Boston
  • Pool
    Dec 23 - Dec 28

    Raffles Boston + Flight

    Back Bay
    5 nights
    5.0 star property
    9.6/10 - Exceptional (357 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $3,232
    CA $2,174
    per traveller
    found 1 day ago
    Raffles Boston

Kittery Foreside Hotel Deals

A two-story brick house with a white porch and a garden with various flowers and plants.

The Water Street Inn

The Water Street Inn
3.5 star property
Kittery Foreside
9.6 out of 10, Exceptional, (243 reviews)
The price is CA $194
CA $212 total
includes taxes & fees
Nov 29 - Nov 30
The Water Street Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Kittery Foreside
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.