Islesboro Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Colleen Johnson

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Islesboro Vacation Packages

Islesboro Hotel Deals

Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

3 out of 5
159 Searsport Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is ₩295,162 per night from Sep 16 to Sep 17
₩295,162
₩321,728 total
Sep 16 - Sep 17
includes taxes & fees
Fireside Inn & Suites - Belfast
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is ₩196,217 per night from Aug 31 to Sep 1
₩196,217
₩227,707 total
Aug 31 - Sep 1
includes taxes & fees
7.6/10 Good! (139 reviews)
"It took awhile to find someone to check in but turns out he was helping someone to fix the tv in their room. Very nice room. Would definitely stay there again."

Reviewed on Aug 24, 2025

Harborline Hotel
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way, Rockport, ME
Fully refundableReserve now, pay when you stay
The price is ₩289,333 per night from Aug 31 to Sep 1
₩289,333
₩315,373 total
Aug 31 - Sep 1
includes taxes & 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

The Country Inn at Camden Rockport
See all 1,336 properties in Islesboro
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.

Frequently asked questions

How much does an Islesboro vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Islesboro costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Islesboro?
Plan your trip for the shoulder or low season and you're likely to find cheap Islesboro vacation packages. Bear in mind that public holidays and major festivals and events can impact prices, so do a little research before you go.
How many days is enough for Islesboro?
The ideal duration of your Islesboro vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to go to all the top sights and discover some hidden treasures along the way.
How to find the best Islesboro package deals?
Finding a cheap Islesboro package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Islesboro package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Islesboro vacation as a package?
You can enjoy significant savings on your Islesboro getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Islesboro?
If you've got your Islesboro travel dates finalized, book early to snap up some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Islesboro?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Islesboro.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Islesboro.
  3. Decide how long to go for: Now that you're up to speed on Islesboro, you can figure out the perfect length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, book the ideal Islesboro vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.