Westbrook Vacations from $491

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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.

The Latest Westbrook vacation packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $756, price is now $491 per person
$491
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Great location beautiful hotel

Reviewed on Jan 9, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $793, price is now $543 per person
$543
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $861, price is now $635 per person
$635
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.

Reviewed on Dec 24, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,458, price is now $1,082 per person
$1,082
per person
Apr 3 - Apr 6
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The room along with the view was spectacular - Beautifully decorated - Clean - Crisp - The Staff - Beyond Helpful!! The location overlooking the Atlantic Ocean even this time of year with the sun and the ocean waves hitting the rocks was like out of a movie!! Their restaurants 5 star in my opinion!! Just the people they have working looking out for you and making sure you are having an experience of a lifetime!! Thank you again Cliff House - See you very soon!!!

Reviewed on Jan 6, 2026

84 Main

84 Main

4 out of 5
Price was $694, price is now $522 per person
$522
per person
Feb 12 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
10/10 Exceptional! (52 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!

Reviewed on Oct 26, 2025

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Discover the most popular places to visit in Westbrook

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.

Happy Wheels Skate Center

What to do in Westbrook

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$15
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

$17
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
See all activities in Westbrook

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
$78 nightly
The price is $85 total per night from Jan 10 to Jan 11
$85 total
Jan 10 - Jan 11
Total with taxes and fees
5.6/10 (1,005 reviews)
.

Reviewed on Dec 31, 2025

Super 8 by Wyndham Portland ME
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $87 total per night from Jan 11 to Jan 12
$87 total
Jan 11 - Jan 12
Total with taxes and fees
7.8/10 Good! (1,319 reviews)
Front desk attendant was very pleasant and helpful. Room was clean and well stocked with towels and toiletries.

Reviewed on Jan 5, 2026

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Jan 25 to Jan 26
$108 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Room was clean and had all amenities.

Reviewed on Jan 6, 2026

The Westin Portland Harborview
See all 2,873 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.

Find the Best Westbrook Vacation Packages

Westbrook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
18,000
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
State Theatre, Higgins Beach and East End Beach

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Frequently asked questions

How much does a Westbrook vacation package cost?
Offering great value package deals from $491 on Expedia, you'll be pleasantly surprised at how much a vacation to Westbrook costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Westbrook?
You can typically find lower rates and greater availability in December, January and February. Explore our cheap Westbrook vacation packages and you could get some excellent off-season deals.
How many days is enough for Westbrook?
Generally, a handful of days is enough to tick off the major attractions during your Westbrook vacation. However, if you want to have more time to kick back or go on day trips, consider extending your itinerary.
How to find the best Westbrook package deals?
Start your search for a Westbrook package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Westbrook package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Westbrook adventure underway.
Is it cheaper to book a Westbrook vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Westbrook vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Westbrook?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Westbrook trip.
How to plan a trip to Westbrook?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Westbrook.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will probably be the biggest expense during your trip to Westbrook.
  3. Use Expedia's trip planning tool to discover Westbrook: Research every part of your trip to Westbrook with this handy planner. Invite your family and friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide your trip length: Consider how long you want to spend exploring Westbrook. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  5. Combine your airfare and accommodations: Once you've settled on your trip dates and duration, book the perfect Westbrook vacation package for you.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some incredible things to do in Westbrook in Westbrook. Book tickets or make reservations in advance to save time and skip the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Westbrook vacation packages?
Your Westbrook trip is meant to be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.