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.
Country Inn at The Mall

Country Inn at The Mall

2 out of 5
per person
Oct 6 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Bangor (BGR)
9.4/10 Exceptional! (2,315 reviews)
Driving by the Country Inn I never would have chosen to book, but we are SO glad that we did! We just needed a quick night on our way from Western NY to Nova Scotia- the check in was quick and friendly, and was right off the expressway. Breakfast included. Everything we needed right there. The only think I would change was the coffee! It was.. less than optimal. Otherwise 110%!

Reviewed on Jul. 22, 2025

Holiday Inn Bangor by IHG

Holiday Inn Bangor by IHG

3 out of 5
per person
Oct 6 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Bangor (BGR)
7.8/10 Good! (1,001 reviews)
Place was great and clean staff was friendly

Reviewed on Jul. 21, 2025

Harborline Hotel

Harborline Hotel

3 out of 5
per person
Oct 6 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Rockland (RKD)
8.6/10 Excellent! (53 reviews)
The facility is newly remodeled but still a little rough around the edges. The room was a bit narrow but everything was new. I had a double queen room which was very narrow. The room included a desk area and a wet bar but had no coffee maker, iron or ironing board. All rooms have outdoor seating of some type but mine overlooked the parking lot with huge storage containers and trash from the remodeling. There was a sliver of a view of the harbor but it was still nice to be able to sit out on the small deck. I would stay here again and, with a few tweaks, this place has potential.

Reviewed on Jul. 22, 2025

Whitehall

Whitehall

3 out of 5
per person
Oct 6 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Bangor (BGR)
9.4/10 Exceptional! (500 reviews)
this is a classic summer resort with beautiful grounds and a phenomenal, large, well decorated lobby

Reviewed on Jul. 21, 2025

Hilton Garden Inn Bangor

Hilton Garden Inn Bangor

3 out of 5
per person
Oct 6 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Bangor (BGR)
9/10 Wonderful! (1,000 reviews)
Would stay here again

Reviewed on Jul. 20, 2025

Ready to book your vacation to Islesboro?

 

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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
Belfast Harbor Inn

Belfast Harbor Inn

3.5 out of 5
91 Searsport Ave, Belfast, ME
The price is CA $245 per night from Jul 27 to Jul 28
CA $245
CA $267 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (1,003 reviews)
"I have two travelers with allergies, they had breakfast options for them which is hard to find. The staff there was also nice - we only stayed one night but would definitely stay there again."

Reviewed on Jul. 20, 2025

Belfast Harbor Inn
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way, Rockport, ME
The price is CA $300 per night from Jul 28 to Jul 29
CA $300
CA $327 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
Great place to stay!!
"Staying at the Country Inn is always as expected. Clean, friendly, comfy, and well appointed rooms with an added attention to details. The fire pit area out back is a lovely spot to sit and relax in the evening. The Country in is close to Camden and all the quaint seaside communities along Rt. 1. ..."

Reviewed on Jul. 20, 2025

The Country Inn at Camden Rockport
See all 1,355 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?
Offering great value package deals from CA $907 on Expedia, you'll be thrilled with how little a vacation to Islesboro costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Islesboro?
Plan your trip for the low or shoulder season and you're likely to find cheap Islesboro vacation packages. Keep in mind that school vacation periods and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Islesboro?
The ideal duration of your Islesboro vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden gems along the way.
How to find the best Islesboro package deals?
Use Expedia's filters to help you find some of the best Islesboro package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Islesboro package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Islesboro vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can customize your Islesboro getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Islesboro?
If you have your Islesboro vacation dates locked in, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Islesboro?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Islesboro.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will likely be the biggest expense during your trip to Islesboro.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Islesboro. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick an Islesboro vacation package that brings all your bookings together.

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