Title: Islesboro Vacation Packages & Trips 2026 from CA $727 | Expedia.ca [Hotels in Islesboro](https://expedia.ca/Islesboro-Hotels.d6339925.Travel-Guide-Hotels)[Vacation Rentals in Islesboro](https://expedia.ca/Islesboro-Vacation-Rentals.d6339925.Travel-Guide-VacationRentals)[Flights to Islesboro](https://expedia.ca/Cheap-Flights-To-Islesboro.d6339925.Travel-Guide-Flights)[Islesboro Car Rentals](https://expedia.ca/Car-Rentals-In-Islesboro.d6339925.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6339925/09d4e36c-169f-4ff4-a573-9f2becf5ef64.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Islesboro Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Colleen Johnson - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Windsor-Chairmakers-Lincolnville.d553248633992553803.Vacation-Attraction), [Schoolhouse Museum](https://www.expedia.ca/Schoolhouse-Museum-Lincolnville.d553248621532668344.Vacation-Attraction) and [Warren Island State Park](https://www.expedia.ca/Warren-Island-State-Park-Maine.d637213991769526272.Vacation-Attraction). 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. ![Trade Winds on the Bay](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/6e8014d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trade Winds on the Bay CA $727 per person Apr 23 - Apr 26 found 1 hour ago Roundtrip non-stop flight included Edmonton (YEG) to Rockland (RKD) 8.4/10 Very Good! (312 reviews) Chris at the front desk was friendly, helpful and welcoming. The room we had was a good size. I didn't realize a one bedroom wouldn't have a bedroom with a door though. Unfortunately the mattress on the pull out couch was stained heavily and there was no replacement available. The pool was very dirty. Lots of clumps of floating grime, hair and a baby wipe. The floor in the bathroom is peeling back and it was mucky underneath. The ocean and vintage vibe is cute, but definitely room for improvement with cleanliness. Reviewed on Feb 1, 2026 ![Harborline Hotel](https://images.trvl-media.com/lodging/12000000/11770000/11764500/11764432/427c5807_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harborline Hotel CA $745 per person Apr 23 - Apr 26 found 1 hour ago Roundtrip non-stop flight included Edmonton (YEG) to Rockland (RKD) 7.6/10 Good! (218 reviews) The room was very clean and staff was friendly and courteous. Reviewed on Nov 7, 2025 ## Ready to book your vacation to Islesboro? Choose your dates ## Islesboro Hotel Deals ![Island log home in Maine with ocean views](https://images.trvl-media.com/lodging/36000000/35170000/35164700/35164619/a90dad88_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Island log home in Maine with ocean views Islesboro ME 10/10 Exceptional! (88 reviews) Everything was perfect! The downside was that the stay was cut short as our work finished early1 Reviewed on Dec 12, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=35164619&PinnedHotelID=35164619&HadPinnedHotel=true®ionId=6339925) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=35164619&PinnedHotelID=35164619&HadPinnedHotel=true®ionId=6339925) ![Trade Winds on the Bay](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/6e8014d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Trade Winds on the Bay 2 Park Dr Rockland ME Fully refundableReserve now, pay when you stay 8.4/10 Very Good! (338 reviews) Clean, large room. Friendly staff. Great location@ Reviewed on Jan 26, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=95445009&PinnedHotelID=95445009&HadPinnedHotel=true®ionId=6339925) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=95445009&PinnedHotelID=95445009&HadPinnedHotel=true®ionId=6339925) ![The Country Inn at Camden Rockport](https://images.trvl-media.com/lodging/2000000/1570000/1570000/1569993/63281d3f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Country Inn at Camden Rockport 8 Country Inn Way Rockport ME Fully refundableReserve now, pay when you stay CA $176 CA $192 total Feb 9 - Feb 10 includes taxes & fees 9.4/10 Exceptional! (1,003 reviews) Clean room, good breakfast, home style, very soft and comfortable bed Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=1569993&PinnedHotelID=1569993&HadPinnedHotel=true®ionId=6339925) [See all 1,303 properties in Islesboro](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=6339925) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app