
Islesboro Vacations from $528
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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.

Trade Winds on the Bay
Price was $638, price is now $528 per person
$528
per person
Oct 21 - Oct 25
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rockland (RKD)
8.4/10 Very Good! (251 reviews)
Check-in was difficult as no one in the front lobby, however, found out he was helping someone with their tv. Room was nice and clean
Reviewed on Aug 27, 2025

3Bedroom2Bath CarriageHouse Pet Friendly
Price was $2,428, price is now $1,791 per person
$1,791
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

The Pathmaker Hotel
Price was $823, price is now $647 per person
$647
per person
Nov 22 - Nov 25
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.8/10 Exceptional! (221 reviews)
Everything about this property was awesome!!! Especially the breakfast!!!! 5 Star!!
Reviewed on Aug 27, 2025

Historic 2 Cats Inn
Price was $1,089, price is now $927 per person
$927
per person
Nov 22 - Nov 25
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
7.4/10 Good! (3 reviews)
The included breakfast was so good and highly recommended. There was an electrical outlet in the bathroom that didn’t work. Also, not sure if it was us, but we couldn’t get the door to lock. However, for the location, cleanliness. We would stay here again. I might recommend a bigger refrigerator since we did have leftovers and they didn’t always fit in the fridge.
Reviewed on Oct 14, 2024

Hearthside Inn
Price was $747, price is now $642 per person
$642
per person
Nov 22 - Nov 25
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
10/10 Exceptional! (183 reviews)
We had a wonderful stay at the Hearthside Inn! The room was spotless and very comfortable, and the customer service was excellent — the staff went above and beyond to make sure we felt welcomed. Parking was a bit of a walk, but they were very helpful in assisting us and offering good options. Breakfast was amazing, and the coffee was just what we needed to start the day. Highly recommend this inn for anyone visiting the area! Thank you again… from Calif!
Reviewed on Aug 27, 2025
Islesboro Hotel Deals

Fireside Inn & Suites - Belfast
159 Searsport Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $221 total per night from Sep 1 to Sep 2
$221 total
Sep 1 - Sep 2
Total with taxes and fees

Harborline Hotel
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $141 total per night from Sep 7 to Sep 8
$141 total
Sep 7 - Sep 8
Total with taxes and fees

The Country Inn at Camden Rockport
8 Country Inn Way, Rockport, ME
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $228 total per night from Aug 31 to Sep 1
$228 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (1,015 reviews)
"Country Inn was a great place to stay. Breakfast was delicious and rooms were clean and neat. Staff was courteous and helpful. Excellent place to stay! Highly recommend!"
Reviewed on Aug 26, 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.