Westbrook Vacation Packages
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Your Westbrook Vacation
Lock in a Westbrook vacation package and get set to experience the best of this city. Consider staying in the neighborhood of Parkside, which is good for festivals, markets and walking. Fill your spare time with visits to University of Southern Maine, Portland Museum of Art and Victoria Mansion, some of the things you simply have to see during your trip to Westbrook. That dream Westbrook vacation is just clicks away. Browse flights, accommodations and more on Expedia for a getaway that's tailored to suit your style.
Top Westbrook Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Price was CA $1,743, price is now CA $1,343 per person
CA $1,343
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Great experience all around. Will definitely visit again if in the area.
Reviewed on May 25, 2026
The Meadowmere Resort
Price was CA $2,239, price is now CA $1,672 per person
CA $1,672
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Clean room , friendly Staff , Breakfast was great !!
Reviewed on May 13, 2026
Cape Arundel Inn and Resort
Price was CA $2,717, price is now CA $2,341 per person
CA $2,341
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (44 reviews)
The room was fantastic and the staff very friendly.
Reviewed on Feb 15, 2026
Westbrook Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $295 per night from May 31 to Jun 1
CA $295
CA $379 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,769 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."
Reviewed on May 25, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $286 per night from May 31 to Jun 1
CA $286
CA $316 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,657 reviews)
"The place is wonderful. Just remember to get water from the lobby because it is not stocked in the rooms."
Reviewed on May 27, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $237 per night from May 31 to Jun 1
CA $237
CA $300 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,223 reviews)
"We stay here every time we visit our daughter in Portland."
Reviewed on May 27, 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.
What to do in Westbrook
Portland Smartphone Audio Tour: Self-Guided Drive
CA $21
per traveller
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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.
