Drakes Island Vacation Packages

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Top Holiday Package Deals in Drakes Island

Price found within the past 48 hours. Click for updated prices.

Inn at St John Portland In-Town

Valley Street

CA $1,177

per person

Oct 23 - Oct 26

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

8.6/10 Excellent! (1,118 reviews)

The Docent's Collection at 178 Middle Street

Downtown Portland

CA $2,058

per person

Oct 23 - Oct 26

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.6/10 Exceptional! (61 reviews)

Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.

Reviewed on Sep 18, 2026

Evalina Hotel

Downtown Portland

CA $2,498

per person

Oct 23 - Oct 26

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

10/10 Exceptional! (11 reviews)

The Docent's Collection at 121 Middle Street

Downtown Portland

CA $1,718

per person

Oct 23 - Oct 26

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.6/10 Exceptional! (382 reviews)

Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.

Reviewed on Sep 18, 2026

Portland Harbor Hotel

Downtown Portland

CA $1,690

per person

Oct 23 - Oct 26

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.2/10 Wonderful! (1,823 reviews)

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

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 Crescent Beach, 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.

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

Ogunquit - The Milestone

687 Main Street Ogunquit ME

CA $112

CA $122 total

Oct 4 - Oct 5

includes taxes & fees

8.8/10 Excellent! (1,547 reviews)

"Room was clean, comfortable and well appointed.. staff was very professional and check-in was fast and easy.. continental breakfast the next morning was great and had lots of offerings"

Reviewed on Sep 20, 2026

Anchorage Inn and Resort

265 Long Beach Avenue York Beach ME

CA $166

CA $181 total

Oct 18 - Oct 19

includes taxes & fees

9/10 Wonderful! (1,254 reviews)

"Amazing time and amazing staff. Thank you"

Reviewed on Sep 19, 2026

Ocean Sands at York Beach

277 Long Beach Avenue York Beach ME

Fully refundableReserve now, pay when you stay

CA $203

CA $249 total

Oct 1 - Oct 2

includes taxes & fees

See all 3,539 properties in Drakes Island

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.