Islesboro Vacations from $327

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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.
Holiday Inn Bangor by IHG

Holiday Inn Bangor by IHG

3 out of 5
Price was $476, price is now $327 per person
$327
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Bangor (BGR)
7.8/10 Good! (1,001 reviews)
Overall stay was good

Reviewed on Aug 12, 2025

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
Price was $2,077, price is now $1,254 per person
$1,254
per person
Oct 24 - Oct 28
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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

Bar Harbor Main Street Apartments

Bar Harbor Main Street Apartments

3.5 out of 5
Downtown Bar Harbor
Save 100% on your flight
Price was $1,871, price is now $1,223 per person
$1,223
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Save 100% on your flight
Price was $1,713, price is now $1,240 per person
$1,240
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Bangor (BGR)
8/10 Very Good! (3 reviews)
Nice spot that is very close to bar harbor. Very clean and great for a large amount of people.

Reviewed on Jun 30, 2025

Hearthside Inn

Hearthside Inn

2.5 out of 5
Price was $566, price is now $429 per person
$429
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
10/10 Exceptional! (182 reviews)
Nice room, #2, Very nice staff, great breakfast, quite, excellent location for walking to everything downtown Bar Harbor. Would definitely go back and stay again.

Reviewed on Aug 15, 2025

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Islesboro Hotel Deals

Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

3 out of 5
159 Searsport Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $231 total per night from Aug 24 to Aug 25
$231 total
Aug 24 - Aug 25
Total with taxes and fees
8.8/10 Excellent! (873 reviews)
"The rooms are large and it is nice that the bedroom area is away from the windows. Beautiful views and home base to explore the beauty of coastal Maine!"

Reviewed on Aug 20, 2025

Fireside Inn & Suites - Belfast
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $150 total per night from Aug 27 to Aug 28
$150 total
Aug 27 - Aug 28
Total with taxes and fees
7.6/10 Good! (134 reviews)
"Great location and friendly staff"

Reviewed on Aug 22, 2025

Harborline Hotel
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 4 to Sep 5
$217 total
Sep 4 - Sep 5
Total with taxes and fees
9.4/10 Exceptional! (1,004 reviews)
"We really enjoyed our stay at this property. The cleanliness was excellent as well as the staff we interacted with. The room was clean and comfortable. Although somewhat outdated, it was quaint. We stayed in the Rockport King Suite that provided most everything we needed. It had a small kitchenette ..."

Reviewed on Aug 20, 2025

The Country Inn at Camden Rockport
See all 1,342 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 $327 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.