Casco Bay Islands Vacations from $779
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The Latest Casco Bay Islands vacation packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street
Downtown Portland
$1,684
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Room was beautiful, new, and clean. Staff upon check in was extremely helpful and courteous, Excellent accommodations. Close to many sights, bars, and restaurants. Would stay again in a heartbeat.
Reviewed on Sep 12, 2026
Inn By The Sea
$1,067
per person
Dec 3 - Dec 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Beautiful location, quiet, but close to beach and shorelines. Lots of thoughtful luxuries provided like beach chairs, buckets, snacks, fruit and a nightly fire with smores.
Reviewed on Sep 11, 2026
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View all tripsStay 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.
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.
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.
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.
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.
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.
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.
Casco Bay Islands Hotel Deals
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$143 nightly
$156 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (3,019 reviews)
"It was fine"
Reviewed on Sep 13, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$81 nightly
$88 total
Sep 16 - Sep 17
Total with taxes and fees
6.4/10 (1,125 reviews)
"The entire hotel was filthy and outdated. The bathroom was disgusting, especially the shower. In addition, it was not pointed out to me in advance, but when I checked in, the gentleman at the desk said there was a $50 incidental fee to cover things that we might do to the room. He said it was refundable ..."
Reviewed on Sep 13, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$118 nightly
$131 total
Sep 27 - Sep 28
Total with taxes and fees
8.2/10 Very Good! (1,688 reviews)
"Good location"
Reviewed on Sep 13, 2026
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.
Find the Best Casco Bay Islands Vacation Packages
Casco Bay Islands Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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- Umbrella Cover Museum
- Bailey Island Vacations
- Spring Point Ledge Lighthouse
- Victoria Mansion
- Eastern Promenade
- Little John Island Preserve
- Land's End Gift Shop
- Portland Head Light
- Bug Light
- Eartha
- Portland Museum of Art
- Bailey Island Bridge
- Visit Bailey Island
- Higgins Beach
- Ll Bean Flagship Store
- International Cryptozoology Museum
- Fort Williams Park
- Mackworth Island State Park
- Two Lights State Park
- Goddard Mansion
- Casco Bay Lines Ferry Terminal
- Clay Play
- Peaks Island Vacations
- Casco Bay
- Chebeague Island Vacations
- Visit Freeport
- Bowdoin College
- Fort Preble
- Visit Portland
- Downtown Portland Vacations
- East End Beach
- Bradbury Mountain State Park
- Visit Old Port
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.