Casco Bay Islands Vacations from $823
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The Latest Casco Bay Islands vacation packages
Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland - Danforth Street.
West End
$915
per person
Sep 21 - Sep 24
just found
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back
Reviewed on Jul 25, 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 top-notch 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.
Umbrella Cover Museum
You can spend time browsing the exhibits at Umbrella Cover Museum during your trip to Peaks Island. Experience the area's great live music and entertainment choices.
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 fascinating museums.
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 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
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
$77 nightly
$83 total
Sep 1 - Sep 2
Total with taxes and fees
7.2/10 Good! (703 reviews)
"Clean. Breakfast was pretty good. Excellent parking. Fridge and microwave in room which was nice. There was a pool but we did not partake but it looked to be in good form. Close to the Interstate and right on Hwy. 1. Room I think had been recently redone, so the decor was nice. The only reason that ..."
Reviewed on Aug 19, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$131 nightly
$145 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,629 reviews)
"Hotel is a bit older but maintained well and clean."
Reviewed on Aug 19, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$96 nightly
$104 total
Sep 9 - Sep 10
Total with taxes and fees
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.
