Westbrook Vacation Packages 2026 from $576

Westbrook flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$576

per person

Jan 21 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

The Docent's Collection at 121 Middle Street

Downtown Portland

Save 100% on your flight

$857

per person

Jan 21 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is also provided.

Portland Regency Hotel & Spa

Downtown Portland

$587

per person

Jan 21 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

The Docent's Collection at 178 Middle Street

Downtown Portland

Save 100% on your flight

$1,069

per person

Jan 21 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

This hotel features free WiFi in public areas, concierge services, and self parking. Express check-in and luggage storage are also provided.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$1,135

per person

Jan 21 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

This bed & breakfast features free WiFi in public areas, concierge services, and self parking. Enjoy the free self-serve breakfast each morning. Luggage storage is also provided.

Top Westbrook hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

$91 nightly

$101 total

Dec 6 - Dec 7

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Spa

Pet friendly

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

$76 nightly

$84 total

Nov 17 - Nov 18

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Pool

Hot Tub

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$86 total

Nov 15 - Nov 16

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Pool

Hot Tub

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$187 total

Nov 22 - Nov 23

Total with taxes and fees

Pet friendly

Free WiFi

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$61 nightly

$66 total

Nov 17 - Nov 18

Total with taxes and fees

This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Breakfast included

Pet friendly

Ramada Plaza by Wyndham Portland

155 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$86 total

Nov 15 - Nov 16

Total with taxes and fees

This hotel features 2 restaurants, 2 hot tubs, and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

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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.

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.

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Frequently asked questions

How much are vacation packages to Westbrook?

Vacation packages, which provide both flights and hotels in Westbrook, are priced from as little as $576. Make your travel dreams a reality and book your trip with Travelocity today.

How long should my Westbrook vacation be?

Your Westbrook trip can be as long or as short as you like, but many travelers stay roughly 2 nights. Like to venture off the beaten path and uncover some hidden treasures? Lock in a couple more nights and experience a different side of this place.

Where can I get the best vacation package deals for Westbrook?

Find your dream escape at Travelocity. With access to 400 airline partners and 1,000,000 properties across the globe, finding the perfect Westbrook package deal couldn't be simpler.

Why should I purchase my Westbrook vacation bundle via Travelocity?

Whether you're on the hunt for the ultimate unplugged escape or after the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of different websites for the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our team of customer service experts are available for you round-the-clock.

Can I save on my Westbrook car rental if I bundle it with hotels and flights?

Combining your hotel, car and flight into a Westbrook vacation package is an easy way to score better prices. Plus, having your own rental car gives you the freedom to find your way to all those famous sights you're eager to check out. Located 100 mi from Westbrook, Fenway Park is one attraction that should be on your agenda. Put together a driving playlist and make a day trip of it.

Which airport is best for Westbrook?

One option is Portland Intl. Jetport Airport (PWM). From here, you'll have to travel northwest for around 4 mi to reach inner Westbrook. Another convenient choice is Augusta State Airport (AUG), 55 mi away from central Westbrook.

What is there to do in Westbrook?

MAGAN Trailhead is just one of the memorable sights that make Westbrook such a tourist hot spot. But give yourself enough time to discover its lesser-known attractions too. This is sometimes where the best memories are created.

Where should I stay when visiting Westbrook?

Many visitors check in to the Sunny spot minutes from Portland. It's sure to be a great base for your Westbrook vacation.