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.
Eden Village Motel & Cottages
Price was CA $1,433, price is now CA $1,190 per person
CA $1,190
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
8.6/10 Excellent! (246 reviews)
The staff is wonderful, it’s convenient to bar harbor but away from the crowds, rooms are charming and very maine.! We will absolutely stay here sharing, wonderful, priced right and charming!
Reviewed on Oct 26, 2025
Moseley Cottage Inn & Town Motel
Downtown Bar Harbor
Price was CA $1,571, price is now CA $1,350 per person
CA $1,350
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
9.4/10 Exceptional! (560 reviews)
Great value for location. Clean rooms, easy check in/out.
Reviewed on Oct 30, 2025
The Pathmaker Hotel
Price was CA $1,612, price is now CA $1,396 per person
CA $1,396
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
9.8/10 Exceptional! (413 reviews)
Wonderful full breakfast. 8 or so options. Included in the stay. 2 mornings. Both delicious.
Location is only a couple tenths of a mile to the center of BH.
We had a delicious dinner one night as well. Chicken parmigiana. Large portions. Perfectly cooked. Shared a MASSIVE Caesar salad. Honestly, too much for two!
Only thing- the pace of dinner left a lot to be desired. Server didn’t ask if we wanted another drink. Entrees came before we were half done with salad. So I’d suggest ordering apps or salad without ordering the entree til close to done.
It IS off-season, and there was only one server for dinner, so that certainly could play into it.
Off-season rates were great! In 3 months, this king room rate will quadruple!!!!!
We absolutely will consider staying here again.
Reviewed on Apr 16, 2026
Anchorage Motel
Price was CA $1,323, price is now CA $1,169 per person
CA $1,169
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
9/10 Wonderful! (1,000 reviews)
Extremely friendly staff. Clean room, close to walking to shops
Reviewed on Jan 23, 2026
Islesboro Hotel Deals
Island log home in Maine with ocean views
Islesboro ME
10/10 Exceptional! (88 reviews)
Everything was perfect! The downside was that the stay was cut short as our work finished early1
Reviewed on Dec 12, 2025
Fireside Inn & Suites - Belfast
159 Searsport Avenue Belfast ME
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Apr 27 to Apr 28
CA $168
CA $183 total
Apr 27 - Apr 28
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
A gem of a spot, friendly staff, quiet big rooms with a nice porch and beach access, great pool/hot tub/sauna. The free coffee was even decent. Excellent experience we’ll be back!
Reviewed on Mar 29, 2026
Trade Winds on the Bay
2 Park Dr Rockland ME
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Apr 27 to Apr 28
CA $124
CA $135 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (376 reviews)
When choosing a hotel I specify two provisions: 1 Parking 2. On site meals. Trade Winds on the Bay failed number 2. Due to pouring rain I missed an evening meal but breakfast in a cafe was excellent. Come on Hotels.com at least be accurate
Reviewed on Apr 14, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
