Bailey Island Vacations from ￥151,522
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The Latest Bailey Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Best Western York Inn
Price was ￥154,976, price is now ￥151,522 per person
￥151,522
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
8.4/10 Very Good! (1,007 reviews)
Room cleanings were not thorough. Bedspread was removed when stained and not replaced for 10 days. We were charged for the bedspread being thrown out, which I found out when I asked what the charge was. I then told the office manager that the bedspread was never replaced upon which it was replaced. I plan to fight this charge.
Reviewed on Sep 17, 2025
Kennebunkport Captains Collection
Price was ￥238,029, price is now ￥202,650 per person
￥202,650
per person
Nov 18 - Nov 24
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
9.4/10 Exceptional! (622 reviews)
We loved the quietness of the property and how walkable it was to downtown
Reviewed on Sep 23, 2025
Find the Best Bailey Island Vacation Packages
Bailey Island Hotel Deals
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥22,784 per night from Oct 19 to Oct 20
￥22,784
￥25,209 total
Oct 19 - Oct 20
includes taxes & fees
7.8/10 Good! (1,091 reviews)
"Not bad at all"
Reviewed on Sep 22, 2025
Germaine Inn South Portland
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is ￥12,729 per night from Oct 26 to Oct 27
￥12,729
￥13,874 total
Oct 26 - Oct 27
includes taxes & fees
7.4/10 Good! (268 reviews)
"Very comfortable bed and pleasant stay. Easy parking and quiet."
Reviewed on Sep 25, 2025
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥20,815 per night from Oct 26 to Oct 27
￥20,815
￥23,029 total
Oct 26 - Oct 27
includes taxes & fees
8.8/10 Excellent! (2,256 reviews)
"Great"
Reviewed on Sep 20, 2025
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.
Discover the most popular places to visit in Bailey Island
Bailey Island Bridge
Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
