Windham Vacations 2025/2026 from CA $578

Windham flight + hotel packages

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

InnSeason Resorts The Falls at Ogunquit

CA $578

per person

Oct 27 - Oct 31

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.

Cliff House Maine

CA $2,220

per person

Oct 27 - Oct 31

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.

Portland Harbor Hotel

Downtown Portland

CA $861

per person

Oct 27 - Oct 31

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Portland Regency Hotel & Spa

Downtown Portland

CA $848

per person

Oct 27 - Oct 31

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

Stay at this 3.5-star 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 Thompson's Point and Maine Mall are located nearby.

Hilton Garden Inn Portland Airport

CA $830

per person

Oct 27 - Oct 31

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Top Windham hotels deals

Clarion Hotel Portland

1230 Congress St, Portland, ME

Free cancellation

Reserve now, pay when you stay

CA $210

CA $232 total

Oct 22 - Oct 23

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 Maine Mall are located nearby.

Pool

Hot tub

Germaine Inn South Portland

675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME

Free cancellation

CA $118

CA $128 total

Oct 22 - Oct 23

includes taxes & fees

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's Point are located nearby.

Pool

Breakfast included

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

340 Park Ave, Portland, ME

Free cancellation

Reserve now, pay when you stay

CA $205

CA $227 total

Oct 22 - Oct 23

includes taxes & fees

Stay at this 3-star 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 Maine Mall are located nearby.

Pool

Breakfast included

Fireside Inn & Suites Portland

81 Riverside St, Portland, ME

Free cancellation

Reserve now, pay when you stay

CA $164

CA $182 total

Oct 23 - Oct 24

includes taxes & fees

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

Pool

Pet-friendly

Portland Harbor Hotel

468 Fore Street, Portland, ME

CA $432

CA $531 total

Oct 23 - Oct 24

includes taxes & fees

Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Pet-friendly

Free WiFi

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

Free cancellation

Reserve now, pay when you stay

CA $471

CA $522 total

Oct 22 - Oct 23

includes taxes & fees

Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

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.

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.

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.

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 $578. 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.