Islesboro Vacations from $780

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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.
Harborline Hotel

Harborline Hotel

3 out of 5
Price was $969, price is now $780 per person
$780
per person
Aug 15 - Aug 20
found 2 hours ago
Roundtrip flight included
Philadelphia (PHL) to Rockland (RKD)
7.6/10 Good! (282 reviews)
The staff were so pleasant and helpful! The location is great.

Reviewed on Jul 12, 2026

Mount Battie Inn

Mount Battie Inn

2.5 out of 5
Price was $1,534, price is now $1,158 per person
$1,158
per person
Sep 4 - Sep 11
found 15 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bangor (BGR)
8.8/10 Excellent! (325 reviews)
I don’t understand the praise - this is a motel-full stop.

Reviewed on Jul 7, 2026

Moseley Cottage Inn & Town Motel

Moseley Cottage Inn & Town Motel

3 out of 5
Downtown Bar Harbor
Price was $1,234, price is now $949 per person
$949
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.4/10 Exceptional! (589 reviews)
Cozy and well maintained

Reviewed on Jul 14, 2026

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $1,287, price is now $1,005 per person
$1,005
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.8/10 Exceptional! (549 reviews)
Great hotel! Easy walk to Main Street but away from noise, super friendly staff, excellent breakfast and amenities, drinking water, coffee and ice provided, clean and spacious room, convenient parking, grocery store across the street. It offers everything we wanted. We really enjoyed our stay. Highly recommend!

Reviewed on Jul 14, 2026

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
Price was $1,602, price is now $1,270 per person
$1,270
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
8.8/10 Excellent! (267 reviews)
We stayed in the motel portion. The location is convenient and our room was ok, but the bathroom had a sliding door with no locking mechanism, which is quite ridiculous when there is a family staying in the room. When I emailed the property twice about this, both emails were ignored. Similarly, I messaged them with a request for "late" checkout (11 am, since their checkout is a ridiculously early 10 am), I received no response.

Reviewed on Jul 13, 2026

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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.
See properties

Islesboro Hotel Deals

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro ME
10/10 Exceptional! (91 reviews)
"Great location!"

Reviewed on Jul 6, 2026

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Island log home in Maine with ocean views
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 Nov 29, 2023

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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
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
$165 nightly
The price is $180 total per night from Jul 15 to Jul 16
$180 total
Jul 15 - Jul 16
Total with taxes and fees
9.6/10 Exceptional! (1,019 reviews)
"Nice cottage in an absolutely gorgeous location, which access to a beach right on the property in front of the cottage. The cottage itself was clean, well-maintained and very comfortable. Kitchen is small but perfectly functional. Large windows facing the ocean (and a porch) mean we spent most of ..."

Reviewed on Jul 13, 2026

Colonial Gables Oceanfront Village
See all 1,544 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.

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 $780 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.