Casco Bay Islands Vacation Packages 2026

Photo by Robbie Martin

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Stay near popular Casco Bay Islands attractions

Mackworth Island State Park

This forested island sanctuary offers a 1.25-mile coastal trail with stunning Casco Bay views. Build tiny homes in the Fairy Village or visit Governor Baxter's pet cemetery while enjoying the tranquil shoreline.

See properties

Sand Beach

9.2/10 (22 reviews)

If a restful vacation is part of your travel plans, Sand Beach might be the perfect place to seek out during your trip to Portland. Wander the area's waterfront or simply enjoy one of its seafood restaurants.

See properties

Little John Island Preserve

Explore a coastal forest path leading to secluded rocky beaches at this 23-acre Maine preserve. Pause on shoreline benches to spot bald eagles while enjoying panoramic ocean views along the 1.3-mile loop trail.

See properties

Fifth Maine Museum

This historic Queen Anne-style museum preserves both Civil War history and Peaks Island's local heritage. Explore two floors of exhibits while enjoying panoramic views of Casco Bay from the wrap-around porch.

See properties

Little Diamond Island

Commune with nature and explore the great outdoors at Little Diamond Island during your travels in Portland. Stroll along the area's waterfront or experience its acclaimed theater scene.

See properties

Umbrella Cover Museum

You can spend time browsing the exhibits at Umbrella Cover Museum during your trip to Peaks Island. Experience the area's entertainment choices and great live music.

See properties

House Island

Commune with nature and explore the great outdoors at House Island during your travels in Portland. Stroll along the area's waterfront or experience its entertainment choices.

See properties

Casco Bay Islands Hotel Deals

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Fully refundable

$69 nightly

$75 total

Nov 1 - Nov 2

Total with taxes and fees

6.4/10 (1,144 reviews)

"This is a very nice property and very clean. Staff were cordial. The hvac system worked well and wasn’t noisy. Room was clean. The room could have used a chair though. There was an office chair at the desk but the back wasn’t stable."

Reviewed on Sep 30, 2026

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

$71 nightly

$78 total

Nov 1 - Nov 2

Total with taxes and fees

8.2/10 Very Good! (1,739 reviews)

"Staff and shuttle were great. Bed comfortable. Bathroom fixtures need attention: shower head pipe loose in the wall. Toilet didn’t stop flushing. (Had to remove tank lid and mess with flapper every time)"

Reviewed on Sep 30, 2026

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME

Fully refundable

$84 nightly

$92 total

Oct 25 - Oct 26

Total with taxes and fees

See all 3,513 properties in Casco Bay Islands

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.