Islesboro Vacations from $597

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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.
Hotel Ursa

Hotel Ursa

4 out of 5
Price was $757, price is now $597 per person
$597
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Bangor (BGR)
9.6/10 Exceptional! (684 reviews)
Ideal location right on campus. Rooms are very clean. The staff is great except that sometimes there’s no one at the front desk and it takes anywhere from 5-10 minutes for a person to arrive.

Reviewed on May 12, 2026

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
Save 100% on your flight
Price was $2,900, price is now $2,014 per person
$2,014
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bangor (BGR)
8.6/10 Excellent! (246 reviews)
Nice with front porch and back patio, grill

Reviewed on May 7, 2026

Ferncrest Acadia

Ferncrest Acadia

2 out of 5
Save 100% on your flight
Price was $2,791, price is now $1,989 per person
$1,989
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bar Harbor (BHB)
9/10 Wonderful! (2 reviews)
The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $3,065, price is now $2,458 per person
$2,458
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bangor (BGR)
9.8/10 Exceptional! (451 reviews)
I’m a Marriott Titanium member and found this hotel to be a great stay! All around charm and in the right location. Great staff. Spacious room. Nice complimentary (not continental) breakfast selections.

Reviewed on May 12, 2026

Harborline Hotel

Harborline Hotel

3 out of 5
Price was $880, price is now $706 per person
$706
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
7.6/10 Good! (253 reviews)
Room was spacious but a bit worn. Fine for a one night stay.

Reviewed on Apr 10, 2026

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Islesboro Hotel Deals

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro ME
10/10 Exceptional! (88 reviews)
Everything was perfect! The downside was that the stay was cut short as our work finished early1

Reviewed on Dec 12, 2025

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Island log home in Maine with ocean views
Camden Riverhouse Hotel

Camden Riverhouse Hotel

2.5 out of 5
11 Tannery Lane Camden ME
$139 nightly
The price is $152 total per night from May 20 to May 21
$152 total
May 20 - May 21
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Great hotel! Loved the closeness to all the food and shopping. Great parking and view of the river.

Reviewed on May 13, 2026

Camden Riverhouse Hotel
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
$139 nightly
The price is $152 total per night from May 18 to May 19
$152 total
May 18 - May 19
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
A great and reasonably priced room close to Camden. Zach was great and welcoming at check in. Hotel room had a nice sitting area, was recently reburbished and offered a decent included breakfast.

Reviewed on May 11, 2026

The Country Inn at Camden Rockport
See all 1,387 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 $597 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.