Islesboro Vacation Packages

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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.

Top Islesboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Ursa

Hotel Ursa

2.5 out of 5
per person
Sep. 3 - Sep. 6
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bangor (BGR)
9.6/10 Exceptional! (30 reviews)
We will definitely come back! What a great place.

Reviewed on May 28, 2024

Cedar Crest Inn

Cedar Crest Inn

2.5 out of 5
per person
Sep. 3 - Sep. 6
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bangor (BGR)
8.8/10 Excellent! (411 reviews)
Carpet and bathroom floor felt wet the entire stay. Other than that, it’s was a great place to stay!

Reviewed on Jun. 8, 2024

Moseley Cottage Inn & Town Motel

Moseley Cottage Inn & Town Motel

3 out of 5
per person
Sep. 3 - Sep. 6
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bangor (BGR)
9.4/10 Exceptional! (313 reviews)
Just leaving after a wonderful 6 night stay. Beautiful location that is convenient to everything. Would stay here again and again!

Reviewed on Jun. 8, 2024

Seasider Motel

Seasider Motel

2.5 out of 5
per person
Sep. 3 - Sep. 6
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bangor (BGR)
9.2/10 Wonderful! (29 reviews)
Comfortable and convenient, walkable to everything. Room was clean and new.

Reviewed on Jun. 7, 2024

Whitehall

Whitehall

3 out of 5
per person
Sep. 3 - Sep. 6
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bangor (BGR)
9.4/10 Exceptional! (355 reviews)
Excellent staff. Very friendly and helpful. Breakfast was very good.

Reviewed on Jun. 6, 2024

Islesboro Hotel Deals

Island log home in Maine with ocean views
Island log home in Maine with ocean views
Islesboro
10/10 Exceptional! (54 reviews)
Highly recommend
"My wife and I thought the property was fantastic. It was well maintained and very clean. If you want a nice quiet getaway I would highly recommend this place."

Reviewed on Nov. 2, 2023

Get rates
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
The price is CA $201 per night from Jun. 12 to Jun. 13
CA $201
CA $220 total
includes taxes & fees
Jun 12 - Jun 13
9.4/10 Exceptional! (1,004 reviews)
"Although there were plenty of seafood restaurants, pizza shops, this area totally lacks a good steak house. If your looking to open up a nice restaurant somewhere, you’d make a killing in Camden/ Rockport with no competition."

Reviewed on Jun. 4, 2024

The Country Inn at Camden Rockport
Fireside Inn & Suites - Belfast
Fireside Inn & Suites - Belfast
3 out of 5
159 Searsport Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jun. 23 to Jun. 24
CA $218
CA $238 total
includes taxes & fees
Jun 23 - Jun 24
8.6/10 Excellent! (635 reviews)
"Beautiful views, excellent room & coffee!"

Reviewed on May 28, 2024

Fireside Inn & Suites - Belfast
See all 1,190 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Islesboro vacation package cost?
Starting from an incredible CA $704, you can create your own Islesboro vacation package. Simply combine flights, hotels and car rentals and we’ll reward you with discounts.
How do I get a cheap travel package to Islesboro?
Bundle your flights and hotels, add on extras such as activities, and save with an Islesboro vacation package. You won’t just pick up big discounts on your trip — you’ll have lots of choice at your fingertips too. When you book through Expedia, you can choose from more than 550 airlines and 1,000,000 hotels globally. Your next grand adventure starts right here, right now!
Where should I stay in Islesboro?
There’s so much to explore in Islesboro, so spend your nights near its best attractions and treat yourself to more time sightseeing. Warren Island State Park is one place to add to your must-see list.
What are the top hotels in Islesboro?
When it comes to comfortable and convenient places to stay in Islesboro, you can’t go past Sweet Three Bedroom Cape On Peaceful Cove. Look up our offers and pick up a great price.
How far in advance should I book my Islesboro vacation?
Reserving your tickets early with Expedia means one less thing to have to worry about. Most air carriers display prices up to 12 months prior to departure dates. Generally, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Islesboro sometimes emerge just a few weeks before departure.
What does an Expedia Islesboro travel package include?
Much of that depends on you. You can choose from a range of Islesboro packages, such as a rental car, hotel and flight. You can also book a flight and a hotel, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Islesboro trip looks like, get set to save!
What should I know before booking an Islesboro travel package?
When you book your flights, hotels and car rentals together, you’ll walk away with awesome discounts. Whether you’re planning a beach escape in a villa or want to stay in a comfortable hotel in the city, Expedia will make it happen for less.
Can I choose my airline with an Islesboro Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Islesboro vacation package?
Yes, you can. We realize life happens, so we’re here to help if you need to make changes to your Islesboro vacation package. You may be able to change or cancel your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Islesboro

Image for Warren Island State Park

Warren Island State Park

Explore the great outdoors at Warren Island State Park, a lovely green space in Islesboro.

Warren Island State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.