Westbrook Vacations from $1,042

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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 $1,252, price is now $1,042 per person
$1,042
per person
Dec 26 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Portland Harbor Hotel is perfectly located, and very beautiful! The staff was extremely helpful and very accommodating. There is a beautiful terrace with a fire pit where we would spend our evenings, which made our stay even better. Our room was beautiful and extremely clean, and we loved the coffee/snack nooks that are on each floor. We will stay here again when visiting Maine!

Reviewed on Nov 15, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $2,849, price is now $2,217 per person
$2,217
per person
Dec 26 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,897, price is now $1,544 per person
$1,544
per person
Dec 26 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,568, price is now $1,288 per person
$1,288
per person
Dec 26 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (136 reviews)

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,964, price is now $1,613 per person
$1,613
per person
Dec 26 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

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Stay near popular Westbrook attractions

Westbrook Performing Arts Center

Enjoy an outing to Westbrook Performing Arts 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

Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour

Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour

$32
per adult
Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour
A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

$49
per adult
98% of travellers recommend
A Walk Through Time Tour in Portland
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$17
per traveler
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Westbrook

Westbrook Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundable
$91 nightly
The price is $101 total per night from Dec 6 to Dec 7
$101 total
Dec 6 - Dec 7
Total with taxes and fees
The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
$76 nightly
The price is $84 total per night from Nov 22 to Nov 23
$84 total
Nov 22 - Nov 23
Total with taxes and fees
8.2/10 Very Good! (1,876 reviews)
"Pool was fun"

Reviewed on Nov 15, 2026

Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Dec 6 to Dec 7
$85 total
Dec 6 - Dec 7
Total with taxes and fees
Fireside Inn & Suites Portland
See all 2,966 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 $1,042 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.