Islesboro Vacations from $662

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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 $793, price is now $662 per person
$662
per person
Mar 15 - Mar 21
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rockland (RKD)
7.6/10 Good! (218 reviews)
The room was very clean and staff was friendly and courteous.

Reviewed on Nov 7, 2025

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $938, price is now $724 per person
$724
per person
Mar 30 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
9.8/10 Exceptional! (332 reviews)
We had an expected appointment in the Bar Harbor area and needed a place to stay for the night. The website was easy to navigate and the hotel is easy to find. They do offer parking under the hotel, but looks limited. Off season we were able to park right next door. The lobby and hotel were nicely decorated and the room was spacious! Loved the corner room. So comfortable and plenty of seating options if you did not want to watch tv in bed. The staff were professional and polite and they have COOKIES in the afternoon! Yeah baby!!! They have a restaurant on site, and the menu has enough options to cover various dietary needs. Off-season, the staff is limited, so be patient and enjoy the views. We would return to Pathmaker during the busier season for sure.

Reviewed on Jan 26, 2026

The Inn on Mount Desert

The Inn on Mount Desert

3 out of 5
Price was $938, price is now $760 per person
$760
per person
Mar 30 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
9.6/10 Exceptional! (1,002 reviews)
We are very pleased with our stay. The room was spotless, very friendly staff & the breakfasts were above our expectations. We definitely will return on our next visit to Bar Harbor ‼️

Reviewed on Jan 26, 2026

Little Fig Hotel

Little Fig Hotel

2.5 out of 5
Price was $855, price is now $696 per person
$696
per person
Mar 30 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
9/10 Wonderful! (829 reviews)
This was a nice motel. The room was comfortable and very clean. They had a nice variety of muffins, yogurt, Kind bars, juice, coffee, teas, and hot chocolate in the mornings. In the evening there were home baked goodies. The staff was so friendly. I would definitely recommend this motel.

Reviewed on Dec 1, 2025

Country Inn at The Mall

Country Inn at The Mall

2 out of 5
Price was $874, price is now $731 per person
$731
per person
Mar 30 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
9.4/10 Exceptional! (2,448 reviews)
Clean room and building as a whole. Friendly staff at check in.

Reviewed on Jan 23, 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

Get rates
Island log home in Maine with ocean views
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr Rockland ME
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $108 total per night from Feb 19 to Feb 20
$108 total
Feb 19 - Feb 20
Total with taxes and fees
8.4/10 Very Good! (337 reviews)
Clean, large room. Friendly staff. Great location@

Reviewed on Jan 26, 2026

Trade Winds on the Bay
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
$129 nightly
The price is $141 total per night from Feb 9 to Feb 10
$141 total
Feb 9 - Feb 10
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
The Inn is very charming and well maintained. the staff were courteous and attentive. the breakfasts were good and the cleaning staff was wonderful. The pool and hot tub were the main feature and look forward to visiting in the summer.

Reviewed on Jan 24, 2026

The Country Inn at Camden Rockport
See all 1,299 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 $662 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.