Islesboro Vacation Packages
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Your Islesboro Vacation
When you organize a vacation package to Islesboro, you can relax and enjoy your getaway knowing your travel plans are in order. Discover the many charms of this amazing city from your base in a neighborhood like Bayside, which is great for history. If sightseeing is on the agenda during your trip to Islesboro, stop by major attractions like Windsor Chairmakers, Schoolhouse Museum and Warren Island State Park. A few quick clicks is all it takes to build your ideal Islesboro vacation on Expedia.
Top Islesboro Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacationland Inn & Suites
Price was CA $1,265, price is now CA $1,175 per person
CA $1,175
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Bangor (BGR)
7.6/10 Good! (1,564 reviews)
No breakfast and no coffee. First time I've ever stayed anywhere and they didn't have anything
Reviewed on Jun 17, 2026
The Pathmaker Hotel
Price was CA $2,849, price is now CA $2,569 per person
CA $2,569
per person
Aug 20 - Aug 23
found 3 hours ago
Roundtrip flight included
St. John's (YYT) to Bangor (BGR)
9.8/10 Exceptional! (516 reviews)
Excellent stay! The hotel was clean, comfortable, and centrally located. The staff was friendly, professional, and always willing to help. I would definitely stay here again and highly recommend it.
Reviewed on Jun 14, 2026
Country Inn at The Mall
Price was CA $1,736, price is now CA $1,568 per person
CA $1,568
per person
Aug 20 - Aug 23
found 3 hours ago
Roundtrip flight included
St. John's (YYT) to Bangor (BGR)
9.4/10 Exceptional! (2,428 reviews)
Breakfast was amazing!! Lots of choices - even for me who has diet challenges.
Quaint little inn in the centre of Bangor - easily accessible to food options, shopping, sightseeing, etc
Room was clean and roomy
Reviewed on Jun 17, 2026
Hotel Ursa
Price was CA $1,807, price is now CA $1,635 per person
CA $1,635
per person
Aug 20 - Aug 23
found 3 hours ago
Roundtrip flight included
St. John's (YYT) to Bangor (BGR)
9.6/10 Exceptional! (711 reviews)
Room was huge the bathroom as well. It’s decorated beautifully. Everyone as so kind. I got coffee both days I stayed from the cafe they weee great. Highly
Recommend
Reviewed on Jun 18, 2026
Islesboro Hotel Deals
Island log home in Maine with ocean views
Islesboro ME
10/10 Exceptional! (89 reviews)
"The cabin was perfect for us, especially the location. Host was very accommodating and available if we had any questions. Will definitely stay here again!"
Reviewed on Jun 16, 2026
The Country Inn at Camden Rockport
8 Country Inn Way Rockport ME
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Jun 25 to Jun 26
CA $252
CA $275 total
Jun 25 - Jun 26
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Great place, would stay agaim"
Reviewed on Jun 16, 2026
Colonial Gables Oceanfront Village
7 Eagle Avenue Belfast ME
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Jun 21 to Jun 22
CA $213
CA $232 total
Jun 21 - Jun 22
includes taxes & fees
9.6/10 Exceptional! (1,003 reviews)
"Lovely expansive view of the ocean. Refrigerator in room, and was pet friendly though our pet stayed home this time."
Reviewed on Jun 17, 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.
Stay near popular Islesboro attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
