Islesboro Vacations

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Find the Best Islesboro Vacation Packages

Islesboro Hotel Deals

Island log home in Maine with ocean views
Island log home in Maine with ocean views
Islesboro
10/10 Exceptional! (69 reviews)
Cozy cabin
"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive."

Reviewed on 8 January 2025

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Island log home in Maine with ocean views
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 AED 437 per night from Apr 2 to Apr 3
AED 437
AED 476 total
includes taxes & fees
2 Apr - 3 Apr
9.4/10 Exceptional! (1,003 reviews)
"Thin Doors to hallways, small TVs in room, soap & lotion in gift shop not supporting local. However supporting local beer. Great breakfast provided as part of your stay."

Reviewed on 30 March 2025

The Country Inn at Camden Rockport
Trade Winds on the Bay
Trade Winds on the Bay
4 out of 5
2 Park Dr, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AED 380 per night from Apr 3 to Apr 4
AED 380
AED 452 total
includes taxes & fees
3 Apr - 4 Apr
8.2/10 Very Good! (199 reviews)
"Excellent experience!"

Reviewed on 28 March 2025

Trade Winds on the Bay
See all 1,209 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 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.