Islesboro Holidays

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Photo by Colleen Johnson

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Your Islesboro Holiday

Prepare to experience Islesboro in your own style with a custom Islesboro holiday package! Uncovering the charms of this city is made easier with a base in a neighbourhood such as Bayside, which is good for history, among many other things. Fill your itinerary with tours of Windsor Chairmakers, Warren Island State Park and Schoolhouse Museum, some of the things you shouldn't miss during your trip to Islesboro. Stop dreaming and start adventuring. Browse the many options on Expedia today and put your Islesboro holiday plans into gear!

Islesboro Holiday

Islesboro Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Knox County Regional Airport (RKD)
Population
630
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Moose Point State Park, Cellardoor Winery and Belfast Historical Society and Museum

Our pick of the best Islesboro Hotel Deals

Beautiful and cozy sanctuary in Islesboro
Beautiful and cozy sanctuary in Islesboro
Islesboro
Get rates
Beautiful and cozy sanctuary in Islesboro
Island log home in Maine with ocean views
Island log home in Maine with ocean views
Islesboro
9.8/10 Exceptional! (71 reviews)
LI traveler
"Good"

Reviewed on 30 May 2025

Get rates
Island log home in Maine with ocean views
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 AU$301 per night from 3 July to 4 July
AU$301
3 July - 4 July
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Location and value
"Awesome value for the area. Would stay here again for sure!!!"

Reviewed on 7 Jun. 2025

Colonial Gables Oceanfront Village
See all 1,334 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an Islesboro holiday package cost?
Offering great value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday 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 holiday 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 holiday 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 holiday as a package?
You can enjoy significant savings on your Islesboro getaway by booking a tailored holiday 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 holiday 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 travelling 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 accommodation: Once you’ve settled on your travel dates and duration, book the ideal Islesboro holiday package for you.

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