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.
River View Resort
Price was CA $2,205, price is now CA $1,589 per person
CA $1,589
per person
Aug 2 - Aug 9
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (324 reviews)
Clean room. Space for everyone, pool was nice, staff was friendly. Perfect for our last minute ski trip.
Reviewed on Apr 12, 2026
The Weldon Hotel
Downtown Portland
Price was CA $5,361, price is now CA $3,727 per person
CA $3,727
per person
Aug 2 - Aug 9
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $3,663, price is now CA $2,616 per person
CA $2,616
per person
Aug 2 - Aug 9
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,762 reviews)
The Portland Harbor Hotel was lovely and very convenient to the tourist area of Portland. The staff were fantastic - very friendly and eager to share recommendations for things to do and places to eat. The hotel restaurant was a great choice for breakfast! And we really enjoyed relaxing at the end of the day by the firepit with our craft cocktails from the bar! It was a very enjoyable stay!
Reviewed on May 22, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $4,739, price is now CA $3,656 per person
CA $3,656
per person
Aug 2 - Aug 9
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (307 reviews)
Beautiful hotel, wonderful location. My only note is that the bed and pillows were not as comfortable as I would expect from this kind of boutique hotel. Standard size pillows only, no king size pillows and no lumbar pillows, and a fairly hard mattress with a thin pad. The night before my stay, I stayed in a converted motel for 25% of the Docent’s price that had far superior bedding.
Reviewed on May 20, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
Price was CA $5,149, price is now CA $4,395 per person
CA $4,395
per person
Aug 2 - Aug 9
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (15 reviews)
Beautiful Loft, sooo clean
Reviewed on May 20, 2026
Westbrook Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from May 25 to May 26
CA $256
CA $335 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,764 reviews)
"Staff ensured our room on check in was quiet. Except there was a night club across the street. Then when asked for a new room was told by staff “that they would bet their career it would be quiet”. The room was one floor up on the same side … Couldn’t sleep until after 1am because of the club across ..."
Reviewed on May 22, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from May 26 to May 27
CA $206
CA $228 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,646 reviews)
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."
Reviewed on May 20, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $230 per night from May 26 to May 27
CA $230
CA $292 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,217 reviews)
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."
Reviewed on May 21, 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 $14
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.
