Windham Vacation Packages 2026 from $753

Windham flight + hotel vacation packages

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

Blind Tiger Portland – Carleton Street

West End

$753

per person

Dec 3 - Dec 6

found 4 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.

Evalina Hotel

Downtown Portland

$1,804

per person

Nov 22 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

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

The Docent's Collection at 178 Middle Street

Downtown Portland

$1,719

per person

Nov 22 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) 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.

The Docent's Collection at 121 Middle Street

Downtown Portland

$1,630

per person

Nov 22 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

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

Blind Tiger Portland - Danforth Street.

West End

$1,668

per person

Nov 22 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) 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 Windham hotels deals

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$88 nightly

$96 total

Oct 18 - Oct 19

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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME

Free Cancellation

$110 nightly

$120 total

Oct 18 - Oct 19

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Free airport shuttle

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$119 total

Oct 18 - Oct 19

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

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$51 nightly

$56 total

Oct 22 - Oct 23

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.

Pool

Breakfast included

Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$118 total

Oct 18 - Oct 19

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$453 nightly

$502 total

Oct 18 - Oct 19

Total with taxes and fees

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.

Pet friendly

Free WiFi

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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 $753. 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.