Search Deals onIslesboro Vacation Packages
Islesboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Northport Inn & Lodge
Price was $907, price is now $828 per person
$828
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Bangor (BGR)
Stay at this lodge in Belfast. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Belfast City Park and Parent Gallery are located nearby.
If you book a stay, be sure to read the fine print and any instructions from staff.
I arrived after 8 pm and there was no one in the office ... just a note stuck on the door saying if you arrive when no one is there, call a phone #. I called twice and got voicemail. Finally I rang a doorbell and a guy showed up to tell me he had sent detailed instructions on my room and how to get in.
I hadn't paid much attention to the note he'd sent two weeks earlier because I was expecting a "normal" hotel experience (someone at reception, etc.). So, this was a surprise.
Also, the room had no coffeemaker, no TV, no Kleenex, and no cups (not even plastic).
Reviewed on Oct 18, 2026
Pine Tree Trail Lodge
Price was $1,761, price is now $1,553 per person
$1,553
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Bangor (BGR)
Book a stay at this spa B&B in Pittsfield. Enjoy free parking, a full-service spa, and a garden. Popular attraction JW Parks Golf Course is located nearby.
Elegant Ocean View Home With Breathtaking Views, Private hot tub & Large Deck
Price was $5,642, price is now $5,073 per person
$5,073
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rockland (RKD)
Stay at this vacation home in Rockport. Popular attractions Beech Hill Preserve and Rockport Marine Park are located nearby.
Hollywood Casino Bangor
Price was $971, price is now $875 per person
$875
per person
Dec 24 - Dec 28
found 3 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Bangor (BGR)
Book a stay at this business-friendly hotel in Bangor. Enjoy a casino, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Cross Insurance Center and Maine Savings Amphitheater are located nearby.
Birch Tree Retreat, 6-bedroom Family Getaway Spot
Price was $4,436, price is now $4,006 per person
$4,006
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rockland (RKD)
Book a stay at this golf vacation home in South Thomaston. Enjoy free parking and a pool table. Popular attractions General Henry Knox Museum and Owls Head Transportation Museum are located nearby.
Hotel Ursa
Price was $1,003, price is now $909 per person
$909
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Bangor (BGR)
Stay at this hotel in Orono. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bangor Mall and Hudson Museum are located nearby.
Lovely and convenient for anyone visiting UMaine Orono.
Reviewed on Nov 14, 2026
Harborline Hotel
Price was $907, price is now $829 per person
$829
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rockland (RKD)
Stay at this hotel in Rockland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Maine Lighthouse Museum and Project Puffin Visitor Center are located nearby.
Waterfront Home With Beautiful bay Views - Near Shops & Dining
Price was $2,618, price is now $2,403 per person
$2,403
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rockland (RKD)
Stay at this vacation home in Owls Head. Enjoy free parking and laundry facilities. Popular attractions Snow Marine Park and Sail Power and Steam Museum are located nearby.
Islesboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Islesboro Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Dec 5 - Wed, Dec 16
TPA
Tampa Intl.
BGR
Bangor Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Tue, Mar 30 - Wed, Apr 7
EWR
Newark Liberty Intl. Airport
BGR
Bangor Intl.
$329 Roundtrip, found 3 days ago
$329
Roundtrip
found 3 days ago
Fri, Jan 29 - Sun, Feb 14
LGA
LaGuardia
BGR
Bangor Intl.
$339 Roundtrip, found 5 hours ago
$339
Roundtrip
found 5 hours ago
Sun, Dec 27 - Mon, Jan 4
JFK
John F. Kennedy Intl.
BGR
Bangor Intl.
$346 Roundtrip, found 3 hours ago
$346
Roundtrip
found 3 hours ago
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