Islesboro Holidays

Photo by Colleen Johnson

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Top hotels in Islesboro

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Islesboro ME
10/10 Exceptional! (18 reviews)
Great Spot
"Excellent host! Great connections on the island for everything. Great information on Ferry status, etc. Cabin is truly rustic, spartan appointments as described. Great location and view west with good weather. Bring your goodies, luxuries from the mainland. Lobsters are available tho!"

Reviewed on 29 Nov 2023

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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro ME
10/10 Exceptional! (90 reviews)
"Amazing vacation! Host was super responsive and available for any questions we had. I absolutely loved the property. Only downside is the ferry from the island to the mainland is kinda pricey, but aside from that it was an excellent trip."

Reviewed on 3 Jul 2026

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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 €161 per night from 9 Jul to 10 Jul
€161
9 Jul - 10 Jul
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Another great stay! Amazing place as always"

Reviewed on 5 Jul 2026

Colonial Gables Oceanfront Village
See all 1,534 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.

Stay near popular Islesboro attractions

Warren Island State Park

This secluded 70-acre Maine island offers primitive camping accessible only by private boat. Hike coastal trails, spot wildlife, and experience the tranquility of a car-free, electricity-free retreat in Penobscot Bay.
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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.

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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.