Casco Bay Islands Vacation Packages 2026 from $616

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The Latest Casco Bay Islands vacation packages

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

Nautical Mile

$616

per person

Dec 18 - Dec 21

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

8.6/10 Excellent! (25 reviews)

I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

The Meadowmere Resort

$682

per person

Dec 18 - Dec 21

found 3 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

8.6/10 Excellent! (1,008 reviews)

Portland Harbor Hotel

Downtown Portland

$842

per person

Nov 23 - Nov 28

found 11 hours ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.2/10 Wonderful! (1,864 reviews)

Excellent, well-situated hotel. Front desk personnel were helpful and courteous. Sean and Simone were so kind in finding us the perfect room to suit our needs. Olivia at the bar in the evening was professional; we enjoyed our conversations with her. Great coffee-nook with perfect additions for a continental breakfast. Thanks to all who helped make our stay so enjoyable.

Reviewed on Oct 20, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

$1,314

per person

Nov 23 - Nov 28

found 11 hours ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (400 reviews)

Cape Arundel Inn and Resort

$1,147

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.8/10 Exceptional! (49 reviews)

Ocean view was amazing and check in was painless and very nice with a glass Of Prosecco given to Us!

Reviewed on Oct 19, 2026

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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 28 - Oct 29

Total with taxes and fees

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

$88 nightly

$97 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.