
Islesboro Vacations from $342
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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.
The Latest Islesboro vacation packages
Price found within the past 48 hours. Click for updated prices.


3Bedroom2Bath CarriageHouse Pet Friendly
Save 100% on your flight
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
7.4/10 Good! (3 reviews)
Loved the charm, cleanliness, decor and location. However, internet was so bad we couldn’t watch more than a few seconds of YouTube at a time. Upstairs shower had the lowest flow we’ve ever seen, even with volume turned up to maximum. Dishwasher was commercial and required many manual steps lifting basket, etc and special soap that we never found. Easier to hand wash. No laundry and outdoor light didn’t work at night so we stepped in dog pooh getting out of the car when we arrived. Beautiful little place that needs some attention.
Reviewed on Oct 11, 2023

Trade Winds on the Bay
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Miami (MIA) to Rockland (RKD)
8.4/10 Very Good! (227 reviews)
Love the location, the staff are wonderful and the coffee shop amazing. Highly recommend. Within walking distance of so much Rockland has to offer.
Reviewed on Jul 28, 2025

Bar Harbor Main Street Apartments
Downtown Bar Harbor
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
9.2/10 Wonderful! (5 reviews)
Very clean, modern space. Property owner was very informative and gave perfect instructions for check in/out.
Apt was in great location, at end of village, in quiet area of town, but within walking distance to everything, no need to drive for Village activities. Included all necessities. Only upgrade I would suggest would be to add a full length mirror in the bedrooms or somewhere in apt. Otherwise, no complaints! Would definitely recommend and stay again!!
Reviewed on Jul 29, 2025

Captain Sweetser's Inn
Save 100% on your flight
per person
Sep 24 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rockland (RKD)
10/10 Exceptional! (115 reviews)
Beautiful property, unique. The owners are wonderful women and they sure can cook! Cant wait to return!
Reviewed on Jul 13, 2025
Islesboro Hotel Deals

Island log home in Maine with ocean views
Islesboro
9.8/10 Exceptional! (73 reviews)
Maine Vacation
"Loved the island life! Would return it was great!"
Reviewed on Jul 14, 2025

The Country Inn at Camden Rockport
8 Country Inn Way, Rockport, ME
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $217 total per night from Sep 2 to Sep 3
$217 total
Sep 2 - Sep 3
Total includes taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"Was in a good location for seeing the area"
Reviewed on Jul 30, 2025

Fort Knox Park Inn
64 Main St, Bucksport, ME
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $196 total per night from Aug 3 to Aug 4
$196 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (678 reviews)
"Our stay at Fort Knox was wonderful. Staff was friendly and helpful. Quiet room and water views amazing. Looking forward to our next stay."
Reviewed on Jul 31, 2025
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.
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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.