Casco Bay Islands Vacation Packages 2026 from $720

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The Latest Casco Bay Islands vacation packages

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

Portland Harbor Hotel

Downtown Portland

$720

per person

Dec 3 - Dec 8

found 4 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.2/10 Wonderful! (1,823 reviews)

Very friendly staff. Great location. Enjoyed our stay.

Reviewed on Sep 28, 2026

Blind Tiger Portland – Carleton Street

West End

$932

per person

Dec 3 - Dec 8

found 4 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (129 reviews)

Great location and cool property. No TV though.

Reviewed on Sep 28, 2026

The Docent's Collection at 178 Middle Street

Downtown Portland

$1,039

per person

Dec 3 - Dec 8

found 4 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (61 reviews)

Amazing rooms amazing staff perfect location absolutely amazing !!!! Can’t wait to Go back

Reviewed on Sep 27, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

$973

per person

Dec 3 - Dec 8

found 4 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (382 reviews)

We have stayed in this Docents Collections building in the recent past and this room did not live up to our expectations. I thought I had booked a two-bedroom with two bathrooms. Perhaps because I inadvertently got onto Expedia's site and also due to booking fairly last minute, we ended up with a corner room with one bath not attached to either of the two bedrooms, and windows that faced a close by brick wall and parking garage. We encourage Docents Collection to invest in a few more amenities for this unit, including waste bins in the bedrooms and more than one pillow and throw in the sitting area. The location is great and the staff is friendly and accommodating.

Reviewed on Sep 27, 2026

Blind Tiger Portland - Danforth Street.

West End

$1,076

per person

Dec 3 - Dec 8

found 4 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (193 reviews)

Place was charming and quirky. Very comfortable and well located.

Reviewed on Sep 18, 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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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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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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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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Casco Bay Islands Hotel Deals

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Fully refundable

$82 nightly

$90 total

Oct 25 - Oct 26

Total with taxes and fees

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

8.4/10 Very Good! (3,011 reviews)

"Nice location about 15 minutes outside of the main hub. Solid breakfast, price, and place to stay."

Reviewed on Sep 28, 2026

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

$93 nightly

$103 total

Oct 25 - Oct 26

Total with taxes and fees

8.2/10 Very Good! (1,730 reviews)

"Older hotel in need of some upgrades. Stains on carpets, mold on the shower curtain and shower grout. Sheer curtains were so old they easily tore. Walls are thin and I could hear the guest on the floor above me peeing. I needed another hotel stay in Portland and did not return to this place."

Reviewed on Sep 28, 2026

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.