Westbrook Vacations from $443

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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.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $745, price is now $443 per person
$443
per person
Dec 30 - Jan 3
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
19.2/10 Exceptional! (249 reviews)
This is in a great location and room was very spacious. Blind in bedroom was broken in down position so it was always dark in there. You are supposed to download an app that requires “always on” connection to Bluetooth to get in, but someone was available to give us card keys instead.

Reviewed on Nov 16, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,299, price is now $718 per person
$718
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Portland (PWM)
19.6/10 Exceptional! (86 reviews)
Loved this place and would definitely stay here next time we go back.

Reviewed on Oct 15, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $944, price is now $575 per person
$575
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Portland (PWM)
18.4/10 Exceptional! (1,668 reviews)
Hotel is so centrally located, you can't beat it. The bar is welcoming and perfect to play cards near the fireplace. Have stayed here a couple times now, and it's the new favorite. Parking is convenient, but a bit pricey at $45/night - but worth the access. Staff are kind and accommodating, rooms are clean and updated.

Reviewed on Nov 20, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,108, price is now $677 per person
$677
per person
Dec 30 - Jan 3
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
19.2/10 Exceptional! (161 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.

Reviewed on Oct 27, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,245, price is now $817 per person
$817
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Portland (PWM)
20/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 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

$17
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Tour of Palace & Monument of Marrakech

Tour of Palace & Monument of Marrakech

$39
per adult
Tour of Palace & Monument of Marrakech
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
See all activities in Westbrook

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 $443 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.