Islesboro Vacations from $607

Book a Hotel + Flight or Car together to unlock savings

Photo by Colleen Johnson

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.
The Inn on Mount Desert

The Inn on Mount Desert

3 out of 5
Price was $641, price is now $607 per person
$607
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.6/10 Exceptional! (1,005 reviews)
From check-in to out everything was perfect. Jenny went way out of her way to make our anniversary special with some delicious macaroons and a hand written note. The breakfast was top notch and all the staff welcoming. Location was close to downtown.

Reviewed on Nov 13, 2026

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $731, price is now $650 per person
$650
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.8/10 Exceptional! (721 reviews)
Beautiful place. Located in a perfect spot. We parked the car and walked everywhere. The complimentary breakfast was impressive.

Reviewed on Nov 13, 2026

The Primrose

The Primrose

3 out of 5
Price was $692, price is now $649 per person
$649
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.6/10 Exceptional! (994 reviews)
So adorable, breakfast was enjoyable, it was a nice walk to the downtown area although it’s not very well lit at night so FYI, you may want to bring a flashlight if you plan on being out after sunset. The beds were really comfortable, we enjoyed the extra plush robes and fancy local soap. The staff was all really nice – it was exactly the experience we were hoping for.

Reviewed on Nov 2, 2026

Camp DeForest

Camp DeForest

4.5 out of 5
Price was $840, price is now $803 per person
$803
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
10/10 Exceptional! (141 reviews)

Bar Harbor Condos

Bar Harbor Condos

2.5 out of 5
Price was $673, price is now $652 per person
$652
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
10/10 Exceptional! (21 reviews)
Property was well appointed. Everything we needed was there. Closer to grocery store. Could walk to main part of town. Nice place in a nice spot.

Reviewed on Nov 12, 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.
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Islesboro Hotel Deals

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...
Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro ME
10/10 Exceptional! (99 reviews)
"The cabin was very nice, clean and quiet. We love all the special pieces of decor you have in the cabin. We added 2 heart rocks we found on one of the beaches. I would recommend the cabin to anyone."

Reviewed on Oct 21, 2026

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Island log home in Maine with ocean views
Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

3 out of 5
159 Searsport Avenue Belfast ME
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $125 total per night from Nov 15 to Nov 16
$125 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Love this place . Rooms are nice . Beautiful views from every room. Stay here every time in area"

Reviewed on Nov 14, 2026

Fireside Inn & Suites - Belfast
See all 1,434 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 $607 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.