Islesboro Vacations from $273

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.
Howard Johnson by Wyndham Bangor

Howard Johnson by Wyndham Bangor

2 out of 5
Price was $366, price is now $273 per person
$273
per person
Dec 29 - Jan 2
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
14.8/10 Exceptional! (1,000 reviews)
Our stay at Howard Johnsons was great. They don't have a restaurant,so we had breakfast at Dennys. That was soso. The motel was clean and the service was good.

Reviewed on Nov 15, 2025

Country Inn at The Mall

Country Inn at The Mall

2 out of 5
Price was $458, price is now $331 per person
$331
per person
Dec 29 - Jan 2
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
18.8/10 Exceptional! (2,448 reviews)
Staff was very polite and very friendly.. room was very clean but the bed was comfortable but mattress was saggy in the middle.

Reviewed on Nov 24, 2025

Black Bear Inn, an Ascend Collection Hotel

Black Bear Inn, an Ascend Collection Hotel

3 out of 5
Price was $383, price is now $288 per person
$288
per person
Dec 29 - Jan 2
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
18/10 Exceptional! (1,001 reviews)
Parking was fine. Breakfast left something to be desired.

Reviewed on Nov 23, 2025

The Lucerne Inn

The Lucerne Inn

3.5 out of 5
Lucerne-in-Maine
Price was $535, price is now $405 per person
$405
per person
Dec 29 - Jan 2
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
17.6/10 Exceptional! (1,001 reviews)
Everyone was very kind and welcoming!

Reviewed on Nov 18, 2025

Quality Inn at Bangor Mall

Quality Inn at Bangor Mall

2.5 out of 5
Price was $387, price is now $307 per person
$307
per person
Dec 29 - Jan 2
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
16.4/10 Exceptional! (1,003 reviews)
As always, clean and welcoming!!

Reviewed on Nov 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Islesboro
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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
$137 nightly
The price is $150 total per night from Dec 9 to Dec 10
$150 total
Dec 9 - Dec 10
Total with taxes and fees
8.8/10 Excellent! (979 reviews)
The staff was awesome. The room was clean. Only downfall was the bed was not comfortable, but there was a beautiful view as well.

Reviewed on Nov 24, 2025

Fireside Inn & Suites - Belfast
Belfast Harbor Inn

Belfast Harbor Inn

3.5 out of 5
91 Searsport Ave Belfast ME
$134 nightly
The price is $146 total per night from Dec 1 to Dec 2
$146 total
Dec 1 - Dec 2
Total with taxes and fees
9.6/10 Exceptional! (1,004 reviews)
perfectly renovated room, clean and thick towels

Reviewed on Nov 22, 2025

Belfast Harbor Inn
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
$179 nightly
The price is $195 total per night from Dec 7 to Dec 8
$195 total
Dec 7 - Dec 8
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
We got a great surprise of hot cider and cookies in the office ! Such a nice ending of a lovely day in Belfast

Reviewed on Oct 29, 2025

Colonial Gables Oceanfront Village
See all 1,284 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.

Find the Best Islesboro Vacation Packages

Islesboro Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Knox County Regional Airport (RKD)
Population
630
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Moose Point State Park, Cellardoor Winery and Belfast Historical Society and Museum

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Islesboro vacation package cost?
Offering great value package deals from $273 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.

Explore a world of travel with Expedia

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