A beach with wooden posts and calm waters reflecting the sky.

Drakes Island Vacation Packages

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The Latest Drakes Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A fire pit surrounded by wicker chairs in a garden setting.
    Dec 25 - Dec 28

    Portland Harbor Hotel + Flight

    Downtown Portland
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,868 reviews)
    "The staff was very friendly and the hotel was very quaint. It was also in the perfect location."
    Reviewed November 15, 2026
    Roundtrip • Vancouver (YVR) - Portland (PWM)
    YVR - PWM • 1 stop PWM - YVR • 1 stop
    CA $1,772
    CA $1,689
    per traveller
    found 1 day ago
    Portland Harbor Hotel
  • A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.
    Dec 25 - Dec 28

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (433 reviews)
    Roundtrip • Vancouver (YVR) - Portland (PWM)
    YVR - PWM • 1 stop PWM - YVR • 1 stop
    CA $2,228
    CA $1,999
    per traveller
    found 1 day ago
    The Docent's Collection at 121 Middle Street
  • A spacious living room with a large window, a round coffee table, and two wooden chairs.
    Dec 25 - Dec 28

    The Docent's Collection at 178 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (90 reviews)
    Roundtrip • Vancouver (YVR) - Portland (PWM)
    YVR - PWM • 1 stop PWM - YVR • 1 stop
    CA $2,256
    CA $2,071
    per traveller
    found 1 day ago
    The Docent's Collection at 178 Middle Street
  • A balcony with a table and chairs, overlooking a street with buildings and parked cars.
    Dec 25 - Dec 28

    Portland Regency Hotel & Spa + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.4/10 - Exceptional (1,819 reviews)
    "Always a great spot to visit old port with amenities that can’t be beat anywhere in the city."
    Reviewed November 15, 2026
    Roundtrip • Vancouver (YVR) - Portland (PWM)
    YVR - PWM • 1 stop PWM - YVR • 1 stop
    CA $1,780
    CA $1,715
    per traveller
    found 1 day ago
    Portland Regency Hotel & Spa
  • An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.
    Dec 25 - Dec 28

    Canopy by Hilton Portland Waterfront + Flight

    Downtown Portland
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,001 reviews)
    "They forgot to clean the room one night. Mistake which compensated pro perla"
    Reviewed November 14, 2026
    Roundtrip • Vancouver (YVR) - Portland (PWM)
    YVR - PWM • 1 stop PWM - YVR • 1 stop
    CA $1,934
    CA $1,868
    per traveller
    found 1 day ago
    Canopy by Hilton Portland Waterfront

Where to stay in Drakes Island

Find the best Drakes Island areas and neighborhoods for the activities you enjoy most. Learn more about Drakes Island
Learn more about Drakes Island
A beach with houses in the background.

Wells Beach

Wells Beach is noteworthy for its beaches, and you can make a stop at top attractions like Wells Beach and Crescent Beach.
A rocky breakwater extending into the sea with a sandy beach on the right.

Moody Beach

When in Moody Beach, you can plan a visit to Moody Beach and Wonder Mountain Fun Park, some noteworthy sights in the nearby area.
A coastal boardwalk with grass on either side and a cloudy sky.

Moody

Moody is well-liked for its beaches and restaurants. If you're hoping to see more of the larger area, Moody Beach and Wonder Mountain Fun Park are some interesting sights nearby to check out.
A rocky breakwater extending into the sea with a sandy beach on the right.

Moody Point

If you're looking for some top things to see and do in Moody Point and surrounding area, you can visit Moody Beach and Crescent Beach.

Charles Chase Corner

Charles Chase Corner might not have many top sights, but Moody Beach and Wells Beach are two attractions nearby that you can check out.

Drakes Island Hotel Deals

A modern restaurant with high tables and orange chairs, a bar area, and a view through large windows.

Holiday Inn Express Wells-Ogunquit-Kennebunk by IHG

Holiday Inn Express Wells-Ogunquit-Kennebunk by IHG
3.0 star property
3.5 km from Drakes Island
9.2 out of 10, Wonderful, (740 reviews)
"Clean, comfortable and handy for touring in the area. Plenty restaurants nearby."
The price is CA $124
CA $135 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Express Wells-Ogunquit-Kennebunk by IHG
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 Drakes Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.