Westbrook Vacations from $590
Book a Hotel + Flight or Car together to unlock savings
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.
Evalina Hotel
Downtown Portland
$1,403
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.
Reviewed on Oct 5, 2026
Blind Tiger Portland - Danforth Street.
West End
$813
per person
Dec 19 - Dec 22
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Adorable stylish house and spacious room comfortable bed. Worth the walk to old port. Will come back!
Reviewed on Oct 6, 2026
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.
Happy Wheels Skate Center
This revitalized roller rink preserves the classic skating experience with dynamic lighting and quality sound. Glide across the smooth surface during themed nights or enjoy a nostalgic yet modern adventure.
MAGAN Trailhead
5.2/10 (5 reviews)
The MAGAN Trailhead leads to Mill Brook Preserve's serene woodland paths where alewives migrate each spring. Cross wooden bridges and explore well-marked trails suitable for various hiking abilities.
What to do in Westbrook
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
Westbrook Hotel Deals
Super 8 by Wyndham Portland ME
208 Larrabee Rd Westbrook ME
$59 nightly
$65 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$83 nightly
$92 total
Nov 1 - Nov 2
Total with taxes and fees
8.2/10 Very Good! (1,751 reviews)
"Room was clean, comfortable and adequate, though very outdated decor and worn furnishings. Bed was comfortable. Public areas like elevator, halls were not very clean and well maintained."
Reviewed on Oct 9, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$135 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does a Westbrook vacation package cost?
Offering great value package deals from $590 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?
- 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.
- 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.
- 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.
- 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.
- Combine your airfare and accommodations: Once you've settled on your trip dates and duration, book the perfect Westbrook vacation package for you.
- 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.
Explore a world of travel with Expedia
- Ogunquit Hotels
- Portland Hotels
- Oceanfront Hotels in Portland
- Westbrook Hotels
- South Portland Hotels
- Kennebunkport Hotels
- Hotels near Portland Intl. Jetport
- Cheap Hotels in Portland
- Oceanfront Hotels in Old Orchard Beach
- Downtown Portland Hotels
- Windham Hotels
- Freeport Hotels
- Old Orchard Beach Hotels
- Pet-Friendly Hotels in Portland
- Old Port Hotels
- Scarborough Hotels
- Hotels with Free Airport Shuttle in Portland
- Wells Hotels
- Flights from Charlotte (CLT) to Portland (PWM)
- Flights from San Francisco (SFO) to Portland (PWM)
- Flights from Jacksonville (JAX) to Portland (PWM)
- Flights from New York (JFK) to Portland (PWM)
- Flights to Portland
- Flights from Washington (IAD) to Portland (PWM)
- Flights from Washington (DCA) to Portland (PWM)
- Flights from Salt Lake City (SLC) to Portland (PWM)
- Flights from Tampa (TPA) to Portland (PWM)
- Flights from Atlanta (ATL) to Portland (PWM)
- Flights from Philadelphia (PHL) to Portland (PWM)
- Flights from Houston (IAH) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
- Flights from Syracuse (SYR) to Portland (PWM)
- Flights from Austin (AUS) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Richmond (RIC) to Portland (PWM)
- Flights from Raleigh (RDU) to Portland (PWM)
- Flights from Phoenix (PHX) to Portland (PWM)
- Flights from Miami (MIA) to Portland (PWM)
- Flights from Las Vegas (LAS) to Portland (PWM)
- Flights from Columbus (CMH) to Portland (PWM)
- Flights from St. Louis (STL) to Portland (PWM)
- Flights from Tucson (TUS) to Portland (PWM)
- Flights from Cincinnati (CVG) to Portland (PWM)
- Flights from White Plains (HPN) to Portland (PWM)
- Flights from Orlando (MCO) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Portland (PDX) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Indianapolis (IND) to Portland (PWM)
- Flights from Minneapolis (MSP) to Portland (PWM)
- Flights from Nashville (BNA) to Portland (PWM)
- Flights from Cleveland (CLE) to Portland (PWM)
- Flights from Seattle (SEA) to Portland (PWM)
- Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)
- Flights from Chicago (ORD) to Portland (PWM)
- Flights from Pittsburgh (PIT) to Portland (PWM)
- Flights from Los Angeles (LAX) to Portland (PWM)
- Flights from Fort Lauderdale (FLL) to Portland (PWM)
- Flights from New York (NYC) to Portland (PWM)
- Flights from Hartford (BDL) to Portland (PWM)
- Flights from Dallas (DFW) to Portland (PWM)
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Denver (DEN) to Portland (PWM)
- Flights from Baltimore (BWI) to Portland (PWM)
- Portland Museum of Art
- Southworth Planetarium
- International Cryptozoology Museum
- Scarborough Beach State Park
- Maine Mall
- Happy Wheels Skate Center
- Children's Museum and Theatre of Maine
- State Street Church
- Visit Portland
- Fort Williams Park
- State Theatre
- Eastern Promenade
- Ll Bean Flagship Store
- Two Lights State Park
- Mclellan-Sweat Mansion
- Downtown Portland Vacations
- Wadsworth-Longfellow House
- Victoria Mansion
- Portland Head Light
- Casco Bay Lines Ferry Terminal
- Windham Vacations
- Maine Military Museum
- Old Orchard Beach Vacations
- East End Beach
- Visit Old Port
- Bug Light
- Thompson's Point
- Mclellan-Sweat House
- Charles Q. Clapp House
- Maine College of Art
- Fitzpatrick Stadium
- Higgins Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.