Islesboro Trips (flight + hotel)

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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
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    Plan, book, and manage your trip all in one place

Top hotels in Islesboro

Harborline Hotel
Harborline Hotel
3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is P9,472 per night from Jul 9 to Jul 10
P9,472
P10,324 total
Jul 9 - Jul 10
includes taxes & fees
8.6/10 Excellent! (46 reviews)
"Clean centrally located to Main St. Staff friendly, a nice afordable stop over."

Reviewed on Jun 23, 2025

Harborline Hotel
Colonial Gables Oceanfront Village
Colonial Gables Oceanfront Village
2.5 out of 5
7 Eagle Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is P8,930 per night from Jul 3 to Jul 4
P8,930
P9,734 total
Jul 3 - Jul 4
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Rooms were clean and comfortable. We loved the balconies."

Reviewed on Jun 22, 2025

Colonial Gables Oceanfront Village
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 P10,802 per night from Jun 26 to Jun 27
P10,802
P11,774 total
Jun 26 - Jun 27
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Lovely place, Lovely staff, lovely everything."

Reviewed on Jun 20, 2025

The Country Inn at Camden Rockport
See all 1,344 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.