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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,262, price is now CA $922 per person
CA $922
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Staff was very helpful, room was clean, and great location! Would definitely stay there again

Reviewed on Jul 14, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $3,159, price is now CA $2,252 per person
CA $2,252
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Wonderful staff ! Very well located !

Reviewed on Jul 15, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,319, price is now CA $966 per person
CA $966
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Great place to stay! Peaceful area with ample parking. Room was clean & spacious! Beds were comfy. Beautiful area with nice areas to sit outside. Close to many things in the area to go see & do.

Reviewed on Jul 14, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $4,313, price is now CA $3,221 per person
CA $3,221
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,700, price is now CA $2,051 per person
CA $2,051
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,682 reviews)
Awesome location

Reviewed on Jul 15, 2026

Ready to book your vacation to Westbrook?

 

Choose your dates

Westbrook Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
The price is CA $204 per night from Jul 28 to Jul 29
CA $204
CA $226 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very good! (1,559 reviews)
"The room was all the way to the end which isn't good for elderly people"

Reviewed on Jul 14, 2026

Clarion Hotel Portland Airport ME
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
The price is CA $404 per night from Jul 26 to Jul 27
CA $404
CA $485 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,268 reviews)
"Clean rooms,welcoming stagf"

Reviewed on Jul 13, 2026

Cambria Hotel Portland Downtown-Old Port
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is CA $508 per night from Jul 26 to Jul 27
CA $508
CA $616 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,788 reviews)
"Wonderful staff ! Very well located !"

Reviewed on Jul 15, 2026

Portland Harbor Hotel
See all 3,099 properties in Westbrook
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.
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Stay near popular Westbrook attractions

Happy Wheels Skate Center

Enjoy an outing to Happy Wheels Skate Center during your stay in Westbrook. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
See properties

What to do in Westbrook

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $24
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

CA $77
per adult
Portland, Maine: Hidden Histories Guided Walking Tour
See all activities in Westbrook

Frequently asked questions

How much does a Westbrook vacation package cost?
You can grab a vacation package to this popular destination from CA $922 on Expedia. But how much your vacation to Westbrook costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Westbrook?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Westbrook vacation packages and you could score some great off-season deals.
How many days is enough for Westbrook?
With about 3 days, you'll have plenty of time to experience popular neighbourhoods such as Downtown Portland and Old Port during your Westbrook vacation. Remember to also add State Theatre and Portland Museum of Art to your must-see list. In the mood for more adventures? Consider exploring outside of Westbrook on day trips and tours.
How to find the best Westbrook package deals?
Finding a cheap Westbrook package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Westbrook package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Westbrook vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Westbrook getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Westbrook?
Secure incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Westbrook break.
How to plan a trip to Westbrook?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Westbrook.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your hotel will probably be the largest expense during your trip to Westbrook.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to get to in Westbrook. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, book the perfect Westbrook vacation package for you.

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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.