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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Oct 17 - Oct 20
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
7.8/10 Good! (1,044 reviews)
Hotel did not look full, I had made my reservation back in April , beginning of, and they stuck us in a room next to the exit of the highway, it was Jake brakes all night from truckers. You’d think that 3-1/2 months in advance hotel reservations, they’d put you in a room away from the exit.. not a good night sleep, having to be at airport at 5 AM, and listening to traffic all night

Reviewed on Aug. 12, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Sep 11 - Sep 14
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
Property is modern and clean and a great choice if staying more than one night. The 5:00 check in time is inconvenient and the additional rates for early check in are ridiculous. Our room was ready early even though the information given before check in stated early check in was not available, so we appreciated that. Bed was okay comfort-wise, but the pillows are awful. The biggest gripe I had was being woken by a very loud family with screaming kids well before 7:30 am on a day we looked forward to sleeping in. If this matters to you, the walls and floors are not very soundproof. This was a very unpleasant way to start the second day of a two-day trip. On a positive note, the staff was available via text and responded to our questions quickly and professionally. One suggestion-an exterior sign. The loft was hard to find, with only small signage on the entry doors which is not easily visible from the street. Overall we were happy and would stay again.

Reviewed on Aug. 11, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 17 - Oct 20
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great hotel love the area

Reviewed on Aug. 11, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 22 - Sep 29
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.8/10 Excellent! (76 reviews)
Great place to go and relax for a few days.

Reviewed on Jul. 20, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
per person
Oct 17 - Oct 20
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
The hotel had everything you needed to enjoy your stay in Portland.

Reviewed on Aug. 11, 2025

Ready to book your vacation to Westbrook?

 

Choose your dates

Westbrook Hotel Deals

Super 8 by Wyndham Portland ME

Super 8 by Wyndham Portland ME

2 out of 5
208 Larrabee Rd, Westbrook, ME
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Sep 7 to Sep 8
CA $95
CA $103 total
Sep 7 - Sep 8
includes taxes & fees
5.6/10 (1,009 reviews)
Ok
"The stay was ok. Nothing to add"

Reviewed on Aug. 10, 2025

Super 8 by Wyndham Portland ME
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Aug 24 to Aug 25
CA $160
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,142 reviews)
"Bed was comfort. Good choice for delivery"

Reviewed on Aug. 9, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $127 per night from Aug 31 to Sep 1
CA $127
CA $139 total
Aug 31 - Sep 1
includes taxes & fees
7.4/10 Good! (132 reviews)
"Everything from Germaine Inn South Portland is pretty good rooms, facilities, pool etc.. I only whish they provide breakfast until 10AM instead of 9AM."

Reviewed on Aug. 11, 2025

Germaine Inn South Portland
See all 3,053 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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What to do in Westbrook

Port City Light Cruise

Port City Lights Cruise

CA $53
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

CA $95
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $49
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
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 $568 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.