Casco Bay Islands Vacations from $529
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The Latest Casco Bay Islands vacation packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
$721
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,022 reviews)
The property including room was very nice. It's on a main road but set down so there is no noise. Breakfast was good. The view from the yard in back was very beautiful and peaceful. People were enjoying the pool. The only slight area of improvement would be the efficient reception team's warmth quotient. Would stay again.
Reviewed on Sep 3, 2026
The Wolfeboro Inn
$757
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
8.2/10 Very Good! (631 reviews)
Just returned from a several-day stay at the Wolfeboro Inn. It was absolutely delightful! Clearly an older establishment, but well-maintained and very clean, cozy, and comfortable. The staff was especially friendly and helpful. Very welcoming! Sweet location right on the lake & close to the lovely downtown - so pretty! Extra kudos also to the tavern…the food is excellent at great prices!
👏🤗👏
Reviewed on Sep 1, 2026
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See all available trips from Columbus to Casco Bay Islands
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.
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.
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.
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
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$92 nightly
$100 total
Sep 13 - Sep 14
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
$113 nightly
$123 total
Sep 7 - Sep 8
Total with taxes and fees
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
$68 nightly
$74 total
Sep 14 - Sep 15
Total with taxes and fees
7.2/10 Good! (770 reviews)
"Many long black hair extensions throughout the room and duvet cover. Bathroom sink had lots of mildew behind the faucet."
Reviewed on Sep 3, 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.