Search Deals onWestbrook Vacation Packages
Westbrook Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland – Carleton Street
Price was $778, price is now $644 per person
$644
per person
Dec 3 - Dec 5
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Beautiful place
Reviewed on Sep 20, 2026
The Docent's Collection at 121 Middle Street
Price was $1,308, price is now $1,017 per person
$1,017
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
The loft was wonderful! Really great location for old port! Really enjoyed our stay! Felt homely! We relaxed and felt so comfortable there! Would recommend!
Reviewed on Sep 24, 2026
The Docent's Collection at 178 Middle Street
Price was $1,473, price is now $1,146 per person
$1,146
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Evalina Hotel
Price was $1,199, price is now $957 per person
$957
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class.
Reviewed on Sep 24, 2026
Portland Regency Hotel & Spa
Price was $876, price is now $737 per person
$737
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
We stay here every-time!
Reviewed on Sep 24, 2026
AWOL Kennebunkport
Price was $1,328, price is now $1,131 per person
$1,131
per person
Dec 3 - Dec 6
found 20 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.
The Wolfeboro Inn
Price was $1,111, price is now $948 per person
$948
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this beach hotel in Wolfeboro. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Lake Winnipesaukee and Hampshire Pewter Co. are located nearby.
The Kennebunk Inn
Price was $821, price is now $710 per person
$710
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.
Westbrook Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Westbrook 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, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 9 hours ago
$185
Roundtrip
found 9 hours ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 8 hours ago
$213
Roundtrip
found 8 hours ago
Tue, Oct 20 - Sat, Oct 31
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
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