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.
Clarion Hotel Portland Airport ME
Price was CA $1,672, price is now CA $1,422 per person
CA $1,422
per person
Jun 20 - Jun 27
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8/10 Very Good! (1,408 reviews)
Nice stay. Hotel needs a bit of an update.
Reviewed on Apr 11, 2026
The McKernan Inn
Price was CA $2,034, price is now CA $1,599 per person
CA $1,599
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (93 reviews)
Beautiful modernized old home. Very clean. Staff was friendly. Bathroom does not have enough storage or shelf space for those women that travel.
Reviewed on Apr 12, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,747, price is now CA $2,214 per person
CA $2,214
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (178 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
Ocean Gate Inn
Price was CA $2,483, price is now CA $2,016 per person
CA $2,016
per person
Jun 20 - Jun 27
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
I loved it! It was a quick day trip, but we definitely will be back!!!
Reviewed on Oct 29, 2025
Westbrook Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Apr 26 to Apr 27
CA $192
CA $213 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
We enjoyed our stay. The only boy issue was a stain on the box spring, which staff took care of almost immediately. Would definitely stay again
Reviewed on Apr 12, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $152 per night from Apr 26 to Apr 27
CA $152
CA $206 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (1,195 reviews)
Disappointed with Friday dinner. Ordered simple burgers and they were burnt. Staff great, though
Reviewed on Apr 12, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Apr 26 to Apr 27
CA $168
CA $239 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,769 reviews)
I had a wonderful stay at Portland Harbor Hotel and would absolutely recommend it! The location is perfect—right in the heart of the Old Port, making it easy to walk to shops, restaurants, and the waterfront. The staff was incredibly friendly and welcoming from the moment we arrived, always going ...
Reviewed on Apr 12, 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
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
CA $13
per traveller
Ultimate Portland Self-Guided Driving GPS Audio Tour
CA $23
per traveller
100% of travellers recommend
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.
