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.
Portland Harbor Hotel
Downtown Portland
Price was CA $1,520, price is now CA $1,284 per person
CA $1,284
per person
May 25 - May 29
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
We could have moved right in and been happy for life. Flawless.
Reviewed on Mar 30, 2026
Inn By The Sea
Price was CA $2,582, price is now CA $2,226 per person
CA $2,226
per person
May 25 - May 29
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PWM)
9.4/10 Exceptional! (304 reviews)
This was my first trip away since having kids 12 years ago. The staff was very friendly, helpful and attentive. The parking lot, lobby, halls and room were very clean. Our dinner and breakfast at the Inn were absolutely delicious. The ingredients were fresh and the flavors complimented each other well. It was difficult to make a choice on what to order. We didn't have a pet with us but did see several dogs during dining and were impressed with dog menu. I would highly recommend to anyone to stay at the Inn and if you are unable to at least have a meal in the restaurant. We are already planning a longer stay next time.
Reviewed on Mar 30, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,022, price is now CA $1,791 per person
CA $1,791
per person
May 25 - May 29
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PWM)
9.6/10 Exceptional! (175 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
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $3,212, price is now CA $2,918 per person
CA $2,918
per person
Jun 26 - Jun 28
found 19 hours ago
Roundtrip flight included
Presque Isle (PQI) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Beautiful space, clean room, friendly and accommodating staff, excellent location
Reviewed on Apr 5, 2026
Westbrook Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Apr 22 to Apr 23
CA $194
CA $214 total
Apr 22 - Apr 23
includes taxes & fees
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $153 per night from Apr 20 to Apr 21
CA $153
CA $207 total
Apr 20 - Apr 21
includes taxes & fees
9.4/10 Exceptional! (1,186 reviews)
Clean, quiet, good stay.
Reviewed on Apr 6, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Apr 12 to Apr 13
CA $164
CA $235 total
Apr 12 - Apr 13
includes taxes & fees
9.2/10 Wonderful! (1,762 reviews)
So lovely, great service
Reviewed on Apr 4, 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.
