Casco Bay Islands Vacation Packages 2026 from $580

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The Latest Casco Bay Islands vacation packages

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

84 Main

$580

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

9.8/10 Exceptional! (58 reviews)

The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

The Meadowmere Resort

$602

per person

Dec 30 - Jan 2

found 16 hours ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

8.6/10 Excellent! (1,008 reviews)

Inn By The Sea

$929

per person

Jan 6 - Jan 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.6/10 Exceptional! (333 reviews)

The Inn was beautiful, the location was perfect, and the staff were lovely. It was the perfect place to renew and refresh.

Reviewed on Oct 19, 2026

Blind Tiger Portland - Danforth Street.

West End

$902

per person

Dec 3 - Dec 6

found 13 hours ago

Roundtrip non-stop flight included

Charlotte (CLT) to Portland (PWM)

9.6/10 Exceptional! (193 reviews)

White Barn Inn & Spa, Auberge Collection

Save 100% on your flight

$1,970

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

9.6/10 Exceptional! (124 reviews)

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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.

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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.

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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.

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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.

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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.

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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.

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Battery Steele

This WWII coastal fortification features a 300-foot tunnel covered in graffiti, blending military history with urban art. Explore the dark corridors with a flashlight while enjoying Peaks Island's natural beauty.

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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.

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Casco Bay Islands Hotel Deals

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundable

$83 nightly

$92 total

Oct 27 - Oct 28

Total with taxes and fees

8.2/10 Very Good! (1,790 reviews)

"Quick night stay for an early flight."

Reviewed on Oct 20, 2026

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

$108 nightly

$119 total

Nov 18 - Nov 19

Total with taxes and fees

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Fully refundableReserve now, pay when you stay

$87 nightly

$96 total

Oct 25 - Oct 26

Total with taxes and fees

8.2/10 Very Good! (1,006 reviews)

"This was a great little spot- close to downtown Portland (about 15 mins). Very cozy rooms and I loved the hot tub. I want to go back in the summer to enjoy the beautiful patio (my trip was during a cold September weekend). Staff were friendly and helpful and their grab and go breakfast had tons of ..."

Reviewed on Oct 20, 2026

See all 3,437 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.