Windham Vacations 2026 from CA $1,021

Windham flight + hotel packages

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

Lake Wentworth Inn

CA $1,021

per person

Aug 7 - Aug 12

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Portland (PWM)

Stay at this hotel in Wolfeboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New Hampshire Boat Museum and Allen Albee Beach are located nearby.

Purity Spring Resort

CA $1,049

per person

Aug 7 - Aug 12

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Portland (PWM)

Book a stay at this ski hotel in Madison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions King Pine Ski Area and Ossipee Lake Marina are located nearby.

Top Windham hotels deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

340 Park Ave Portland ME

Free cancellation

Reserve now, pay when you stay

CA $184

CA $203 total

Jun 8 - Jun 9

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free cancellation

CA $164

CA $182 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.

Portland Harbor Hotel

468 Fore Street Portland ME

Free cancellation

Reserve now, pay when you stay

CA $312

CA $399 total

Jun 7 - Jun 8

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free cancellation

Reserve now, pay when you stay

CA $318

CA $390 total

Jun 7 - Jun 8

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Pet-friendly

Free WiFi

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free cancellation

Reserve now, pay when you stay

CA $307

CA $339 total

Jun 7 - Jun 8

includes taxes & fees

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Hot tub

Spa

The Westin Portland Harborview

157 High St Portland ME

Free cancellation

Reserve now, pay when you stay

CA $319

CA $353 total

Jul 1 - Jul 2

includes taxes & fees

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Don't see what you're looking for?

See all available properties in Windham

View all properties

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

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.

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.

Windham Vacations

You've booked your flight and packed your suitcase, but how much do you know about your next unforgettable vacation destination? Sit back, relax and let us talk you through Windham.

If you take a trip 11 miles (18 kilometers) west of Yarmouth, or 12 miles (19 kilometers) northwest of Portland, you'll be in the heart of Windham.

Places to visit in Windham

Whether you're a pinball hotshot or an complete amateur, Seacoast Adventure has an impressive selection of arcade machines and activities to suit all ages. Need some more options? Enjoy a walk on the wild side! Treat the family to a day at Maine Wildlife Park and watch the kids' smiles come alive as they encounter some of the wonders of the animal world. And that's not all there is. Whether you like to think of yourself as an intellectual or simply want to discover a bit more about the region's long history of innovation, St Josephs College is sure to inspire and enlighten.

Where do you fly into for Windham?

Nothing comes close to finally landing in a completely new destination. If you're heading to Windham, chances are you'll step out into Portland International Jetport Airport (PWM). It's approximately 11 miles (18 kilometers) to the southeast of the downtown area. Pick up your belongings and get ready to kick-start your vacation!

Frequently asked questions

How much are vacation packages to Windham?

You can score a fantastic flight and hotel bundle for as low as CA $1,021. 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 161 kilometers 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), 14 kilometers southeast of the city center, is where many people begin their adventures in Windham. But Augusta State Airport (AUG) (80 kilometers 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.