Islesboro Holidays

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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

Island log home in Maine with ocean views
Island log home in Maine with ocean views
Islesboro
9.8/10 Exceptional! (72 reviews)
"This is a beautiful cabin on an island off the coast of Maine. The cabin is beautiful inside and out. The owner did a good job of getting us into the property on our arrival day. If you want a quiet, relaxing place, this is for you. Do be prepared for an expensive ferry ride to and from the island. ..."

Reviewed on 6 Jun 2025

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Island log home in Maine with ocean views
Belfast Harbor Inn
Belfast Harbor Inn
3.5 out of 5
91 Searsport Ave, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is €167 per night from 21 Jul to 22 Jul
€167
21 Jul - 22 Jul
includes taxes & fees
9.6/10 Exceptional! (1,010 reviews)
Everything I want for an overnight stay.
"Friendly, the folks you need are always there, the rooms are generous in size and comfort, and view of ocean from breakfast dining room! Always clean. Non-corporate feel but everything feels very professionally managed."

Reviewed on 8 Jul 2025

Belfast Harbor Inn
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 €204 per night from 17 Jul to 18 Jul
€204
17 Jul - 18 Jul
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Family vacay
"This place is wonderful. Very relaxing and well-appointed in an understated way."

Reviewed on 8 Jul 2025

The Country Inn at Camden Rockport
See all 1,351 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 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.