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.
Acadia Pines Motel

Acadia Pines Motel

2.5 out of 5
Price was CA $1,819, price is now CA $1,721 per person
CA $1,721
per person
Aug 19 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Bangor (BGR)
7.4/10 Good! (304 reviews)
Perfect location. Clean and comfortable.

Reviewed on Jul 1, 2026

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was CA $2,473, price is now CA $2,251 per person
CA $2,251
per person
Aug 19 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Bangor (BGR)
9.8/10 Exceptional! (549 reviews)
We stayed at Pathmaker for 4 nights and had a great time in bar harbor. This hotel is new and very clean. Cleaning service did a wonderful job. Front desk staff is pleasant and helpful. Free breakfast is of the best quality that I have seen in a hotel so far. Overall I would highly recommend this place to families.

Reviewed on Jul 3, 2026

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
Price was CA $2,068, price is now CA $1,941 per person
CA $1,941
per person
Aug 19 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Bangor (BGR)
8.8/10 Excellent! (266 reviews)
Terrible stay—highly disappointed.The reading lamp above the bed was heavily layered with dust chunks. There was also a severe issue with the drainage system. A strong, foul odor resembling urine backed up from the bathroom sink, making it unbearable to shower or brush my teeth. The smell even reached the bedroom area while I was in bed. Additionally, the water had a distinct fishy odor, leaving my hair smelling like it even after a wash. It was an extremely unpleasant experience overall.

Reviewed on Jul 2, 2026

Yellow House Inn

Yellow House Inn

3 out of 5
Downtown Bar Harbor
Price was CA $2,334, price is now CA $2,213 per person
CA $2,213
per person
Aug 19 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Bangor (BGR)
10/10 Exceptional! (70 reviews)
The staff were very accommodating. They thought of everything! From backpacks and umbrellas you can borrow for the day to complimentary snacks and coffee, the Yellow House Inn makes traveling easy. The location is perfectly located near everything in town. We walked to every store and restaurant, the shore path, and Bar Island. The national park entrance is only minutes away. We were on an anniversary trip, and I couldn’t recommend it enough to other travelers looking for a quiet, convenient, and charming place to stay!

Reviewed on Jun 14, 2026

Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
Price was CA $2,004, price is now CA $1,903 per person
CA $1,903
per person
Aug 19 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Bangor (BGR)
7.6/10 Good! (98 reviews)
Staff was nice and friendly

Reviewed on Jun 28, 2026

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 ME
10/10 Exceptional! (90 reviews)
"Amazing vacation! Host was super responsive and available for any questions we had. I absolutely loved the property. Only downside is the ferry from the island to the mainland is kinda pricey, but aside from that it was an excellent trip."

Reviewed on Jul 3, 2026

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Island log home in Maine with ocean views
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Islesboro ME
10/10 Exceptional! (18 reviews)
Great Spot
"Excellent host! Great connections on the island for everything. Great information on Ferry status, etc. Cabin is truly rustic, spartan appointments as described. Great location and view west with good weather. Bring your goodies, luxuries from the mainland. Lobsters are available tho!"

Reviewed on Nov 29, 2023

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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

2.5 out of 5
7 Eagle Avenue Belfast ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Jul 5 to Jul 6
CA $210
CA $229 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"Haven’t been there in about 40 + years and it’s exactly what I remember it was.pet very friendly staff very nice the views are amazing.. can’t wait to make it back again"

Reviewed on Jul 4, 2026

Colonial Gables Oceanfront Village
See all 1,443 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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Stay near popular Islesboro attractions

Warren Island State Park

You can take time to visit Warren Island State Park during your travels to Islesboro.
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Frequently asked questions

How much does an Islesboro vacation package cost?
Offering great value package deals from CA $1,721 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.

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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.