Islesboro Vacations from $479
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Your Islesboro Vacation
When you organize a vacation package to Islesboro, you can relax and enjoy your getaway knowing your travel plans are in order. Discover the many charms of this amazing city from your base in a neighborhood like Bayside, which is great for history. If sightseeing is on the agenda during your trip to Islesboro, stop by major attractions like Windsor Chairmakers, Schoolhouse Museum and Warren Island State Park. A few quick clicks is all it takes to build your ideal Islesboro vacation on Expedia.
The Latest Islesboro vacation packages
Price found within the past 48 hours. Click for updated prices.
Elsa's Inn on the Harbor
$479
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Bar Harbor (BHB)
9.4/10 Exceptional! (242 reviews)
This is where you would want to go if you want to stay someplace quiet out of the main touristy area of Bar Harbor. The Inn is very cute like staying at your grandmother’s, it is across the street from Prospect Harbor. We rode in on a motorcycle in the rain from Bar Harbor and Gale was at the door to greet us with two dry towels. She reviewed the map of the Schoodic Peninsula gave us helpful tips and places where we could go to eat. The included breakfast each morning was delicious and a great way to start the day before heading out for site seeing. It’s about an hour to Mount Desert Island, but only a few minutes away from the Schoodic Peninsula, which is much less populated, and worth a visit.
Reviewed on Aug 28, 2026
Mount Battie Inn
$1,142
per person
Oct 6 - Oct 11
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
8.8/10 Excellent! (335 reviews)
The staff were very kind and available. The landscaping and common spaces were immaculate. The room was quite comfortable, although the bed was not.
Reviewed on Aug 24, 2026
The Primrose
$706
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Bangor (BGR)
9.6/10 Exceptional! (984 reviews)
Everything was great. Very clean and well maintained. Staff was eager to help and friendly. Food was fresh and excellent. We had a very nice stay. Highly recommend the Primrose.
Reviewed on Aug 26, 2026
Whitehall
$1,115
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.2/10 Wonderful! (699 reviews)
Beautiful home with a nice porch with chairs, fireplace and beautiful flowers Relaxing to sit and read or enjoy a glass of wine.
Reviewed on Aug 28, 2026
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.
Islesboro Hotel Deals
Island log home in Maine with ocean views
Islesboro ME
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 Nov 29, 2023
Fireside Inn & Suites - Belfast
159 Searsport Avenue Belfast ME
Fully refundableReserve now, pay when you stay
$151 nightly
$165 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"Could use some over all updating. Nice size tv for a hotel room. For $300 a night, at least a continental breakfast should be included. Only free coffee & tea."
Reviewed on Aug 28, 2026
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.
Find the Best Islesboro Vacation Packages
Islesboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Knox County Regional Airport (RKD) |
Population | 630 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Moose Point State Park, Cellardoor Winery and Belfast Historical Society and Museum |
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Frequently asked questions
How much does an Islesboro vacation package cost?
Offering great value package deals from $479 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?
You can usually find reduced prices and better availability in November, December and January. Browse our cheap Islesboro vacation packages and you could land some great off-season deals.
How many days is enough for Islesboro?
With a well-planned itinerary, you can easily tick off the top Islesboro attractions in a handful of days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Islesboro vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Islesboro vacation packages?
Your Islesboro getaway is meant to be an escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
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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.
