Windham Vacation Packages 2025/2026 from $599

Windham flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$599

per person

Jan 26 - Jan 30

found 1 hour ago

Roundtrip non-stop flight included

Philadelphia (PHL) 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 Weldon Hotel

Downtown Portland

$688

per person

Jan 26 - Jan 30

found 2 hours ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Portland (PWM)

A 24-hour gym, self parking, and a virtual front desk are featured at this aparthotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Free WiFi in public areas is also provided.

Blind Tiger Portland - Danforth Street.

West End

$723

per person

Jan 26 - Jan 30

found 1 hour ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.

The Docent's Collection - Boyd Block

Downtown Portland

$716

per person

Jan 26 - Jan 30

found 1 hour ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Portland (PWM)

This hotel features free WiFi in public areas, concierge services, and self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Luggage storage is also provided.

The Docent’s Collection – Thompson Block

Downtown Portland

$623

per person

Jan 26 - Jan 30

found 1 hour ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Portland (PWM)

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

Top Windham hotels deals

Dormir

965 Roosevelt Trail Windham ME

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$101 total

Nov 23 - Nov 24

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. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$92 total

Nov 30 - Dec 1

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

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$98 total

Dec 7 - Dec 8

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

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$142 nightly

$157 total

Nov 23 - Nov 24

Total with taxes and fees

Pet friendly

Free WiFi

DoubleTree by Hilton Hotel Portland

363 Maine Mall Rd South Portland ME

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$81 total

Nov 26 - Nov 27

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and a free airport shuttle. A business center, a coffee shop, and free WiFi in public areas are also on offer.

Pool

Free airport shuttle

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$78 nightly

$86 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.

Pool

Free airport shuttle

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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.

Popular places to visit

Seacoast Adventure

5/5(4 reviews)

Bring the family to Seacoast Adventure and enjoy some excitement at this amusement park in Windham. Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.

Mercy Primary Care

Though Mercy Primary Care might be what brings you to town, perhaps you'll have a chance to explore more of Windham while you are here.

Frequently asked questions

How much are vacation packages to Windham?

You can score a fantastic flight and hotel bundle for as low as $599. With one of our Travelocity vacation packages, an escape to Windham has never looked more irresistible! Save some time and money and get an early start with packing your suitcases.

How long should my Windham vacation be?

Many travelers pack their suitcase and explore the sights of Windham for about 2 nights. That's a good starting point, but don't be restricted by it. Whether you only stay a couple of nights to see the big attractions or stick around to experience this place like a local, an unforgettable journey awaits.

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

You'll find a fantastic range of Windham package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, putting together your dream escape will be a breeze.

Why should I book my Windham vacation package with Travelocity?

From our 24/7 customer support to our range of terrific destinations, we are committed to giving you the most unforgettable vacation. All you have to do is click and book — our Price Match Guarantee will ensure you score the cheapest price.

Can I save money on my Windham car rental if I book it with hotels and flights?

Bundling your flight, hotel and car into a Windham vacation package is an excellent way to land the best prices. Plus, having your own wheels gives you freedom to get to all those big-name sights you want to explore. Sitting 100 mi away from Windham, Fenway Park is one place that should be on your itinerary. Load up the car and make a day trip of it.

Which airport is best for Windham?

Portland Intl. Jetport Airport (PWM), 9 mi southeast of the city center, is where many people begin their adventures in Windham. But Augusta State Airport (AUG) (50 mi away from central Windham) could be the more convenient option for you.

What is there to do in Windham?

You'll feel a particular magic in the air as you roam the streets of Windham. Maine Wildlife Park and Seacoast Adventure are just two attractions that make this city so popular, so put them at the top of your travel itinerary.

Where should I stay when visiting Windham?

Many visitors check in to the Microtel Inn & Suites By Wyndham Windham. It's the perfect base for your Windham escape.