Westbrook Vacation Packages 2026 from $471

Westbrook flight + hotel vacation packages

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

Ogunquit River Inn & Suites

Moody

$471

per person

Oct 13 - Oct 16

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

Evalina Hotel

Downtown Portland

Save 100% on your flight

$1,336

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$2,105

per person

Sep 20 - Sep 25

found 6 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

The Meadowmere Resort

$530

per person

Oct 13 - Oct 16

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a sauna on site.

Dormir

$783

per person

Sep 20 - Sep 25

found 6 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Westbrook hotels deals

Super 8 by Wyndham Portland ME

208 Larrabee Rd Westbrook ME

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$79 total

Sep 8 - Sep 9

Total with taxes and fees

This motel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. Luggage storage is provided and the front desk is staffed around-the-clock.

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$93 nightly

$101 total

Sep 9 - Sep 10

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$96 nightly

$105 total

Aug 17 - Aug 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.

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

$131 nightly

$145 total

Sep 1 - Sep 2

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.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

$341 nightly

$377 total

Aug 30 - Aug 31

Total with taxes and fees

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.

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$117 total

Sep 8 - Sep 9

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.

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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 $471. 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.