Cliff Island Vacations from $302
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The Latest Cliff Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Cliff House Maine
Save 100% on your flight
Price was $1,136, price is now $702 per person
$702
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Beautiful hotel. Loved the hot-tub and pool, on site restaurants were absolutely incredible and the day spa was perfect! All of the staff were lovely and helpful
Reviewed on Nov 7, 2025
84 Main
Save 100% on your flight
Price was $622, price is now $428 per person
$428
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
10/10 Exceptional! (51 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!
Reviewed on Oct 26, 2025
The Kennebunk Inn
Price was $745, price is now $593 per person
$593
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
7.8/10 Good! (738 reviews)
The room was very clean , the front staff was very helpful and sweet!
Only thing that was a downside (but makes sense) due to the age of the building you can hear everything.
If you are a light sleeper bring a fan to drown out some noise !
Hopefully will be back soon!
Reviewed on Nov 9, 2025
Kennebunkport Captains Collection
Price was $927, price is now $740 per person
$740
per person
Feb 7 - Feb 11
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (634 reviews)
Our Bed and Breakfast was amazing! The bed was comfortable and we loved the salted chocolate chip cookies at night! The staff was so kind and hospitable!
Reviewed on Nov 2, 2025
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Portland Harbor Hotel
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $183 total per night from Nov 16 to Nov 17
$183 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,666 reviews)
Great rooms, walk-able to everything, super clean, great staff, the restaurant is delicious and the bar has good drinks, very accommodating and lots of extras! The 4 stars are for parking... we would like to keep our car inside the garage, to do so it must be valet, that is not an option for some ...
Reviewed on Nov 12, 2025
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 20 to Nov 21
$92 total
Nov 20 - Nov 21
Total with taxes and fees
7.8/10 Good! (1,222 reviews)
I've stayed here a few times and have always had a good experience. Staff is always welcoming and the rooms are
Reviewed on Nov 9, 2025
Tru by Hilton Portland Airport Area
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Nov 20 to Nov 21
$86 total
Nov 20 - Nov 21
Total with taxes and fees
8.8/10 Excellent! (1,609 reviews)
Absolutely
Reviewed on Nov 12, 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.
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