Windham Vacation Packages 2026 from $358

Windham flight + hotel vacation packages

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

Admiral Peary Inn

$358

per person

Dec 11 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A coffee shop, a garden, and a snack bar/deli are also on offer.

Inn By The Sea

$854

per person

Dec 9 - Dec 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

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 business center, laundry service, and free valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

The Docent's Collection at 121 Middle Street

Downtown Portland

$615

per person

Dec 9 - Dec 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

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

Waldo Emerson Inn

$550

per person

Dec 11 - Dec 13

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Portland (PWM)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A business center, a terrace, and a garden are also on offer.

Portland Harbor Hotel

Downtown Portland

$492

per person

Dec 9 - Dec 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Top Windham hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$112 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

$81 nightly

$89 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, 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

$88 nightly

$97 total

Nov 9 - Nov 10

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

$163 nightly

$180 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 12 - Nov 13

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 11 - Nov 12

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 Windham attractions

beach near Boathouse Beach Lane

Why not spend a lazy afternoon at beach near Boathouse Beach Lane during your trip to Windham? Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.

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Frequently asked questions

How much are vacation packages to Windham?

You can score a fantastic flight and hotel bundle for as low as $358. 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.