Islesboro Vacations from $342

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.
Harborline Hotel

Harborline Hotel

3 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Miami (MIA) to Rockland (RKD)
8.6/10 Excellent! (53 reviews)
Place is great. Walk to water,downtown, and restraunts, room was very clean. We will be staying here again.

Reviewed on Jul 31, 2025

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
7.4/10 Good! (3 reviews)
Loved the charm, cleanliness, decor and location. However, internet was so bad we couldn’t watch more than a few seconds of YouTube at a time. Upstairs shower had the lowest flow we’ve ever seen, even with volume turned up to maximum. Dishwasher was commercial and required many manual steps lifting basket, etc and special soap that we never found. Easier to hand wash. No laundry and outdoor light didn’t work at night so we stepped in dog pooh getting out of the car when we arrived. Beautiful little place that needs some attention.

Reviewed on Oct 11, 2023

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Miami (MIA) to Rockland (RKD)
8.4/10 Very Good! (227 reviews)
Love the location, the staff are wonderful and the coffee shop amazing. Highly recommend. Within walking distance of so much Rockland has to offer.

Reviewed on Jul 28, 2025

Bar Harbor Main Street Apartments

Bar Harbor Main Street Apartments

3.5 out of 5
Downtown Bar Harbor
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
9.2/10 Wonderful! (5 reviews)
Very clean, modern space. Property owner was very informative and gave perfect instructions for check in/out. Apt was in great location, at end of village, in quiet area of town, but within walking distance to everything, no need to drive for Village activities. Included all necessities. Only upgrade I would suggest would be to add a full length mirror in the bedrooms or somewhere in apt. Otherwise, no complaints! Would definitely recommend and stay again!!

Reviewed on Jul 29, 2025

Captain Sweetser's Inn

Captain Sweetser's Inn

2 out of 5
Save 100% on your flight
per person
Sep 24 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rockland (RKD)
10/10 Exceptional! (115 reviews)
Beautiful property, unique. The owners are wonderful women and they sure can cook! Cant wait to return!

Reviewed on Jul 13, 2025

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Islesboro Hotel Deals

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro
9.8/10 Exceptional! (73 reviews)
Maine Vacation
"Loved the island life! Would return it was great!"

Reviewed on Jul 14, 2025

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Island log home in Maine with ocean views
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
$199 nightly
The price is $217 total per night from Sep 2 to Sep 3
$217 total
Sep 2 - Sep 3
Total includes taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"Was in a good location for seeing the area"

Reviewed on Jul 30, 2025

The Country Inn at Camden Rockport
Fort Knox Park Inn

Fort Knox Park Inn

2 out of 5
64 Main St, Bucksport, ME
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $196 total per night from Aug 3 to Aug 4
$196 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (678 reviews)
"Our stay at Fort Knox was wonderful. Staff was friendly and helpful. Quiet room and water views amazing. Looking forward to our next stay."

Reviewed on Jul 31, 2025

Fort Knox Park Inn
See all 1,350 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.

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Frequently asked questions

How much does an Islesboro vacation package cost?
Offering great value package deals from $342 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.