Book Exclusive Windham Vacation Packages

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Windham flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,470, price is now CA $1,008 per person
CA $1,008
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,624, price is now CA $1,126 per person
CA $1,126
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,731, price is now CA $1,328 per person
CA $1,328
per person
Sep 20 - Sep 24
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
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 Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
River View Resort

River View Resort

2.5 out of 5
Price was CA $1,659, price is now CA $1,302 per person
CA $1,302
per person
Sep 8 - Sep 15
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,290, price is now CA $1,851 per person
CA $1,851
per person
Sep 20 - Sep 24
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Higgins Beach and Portland Head Light are located nearby.

Top Windham hotels deals

Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free cancellation
The price is CA $130 per night
CA $130
CA $142 total
Sep 6 - Sep 7
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.
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free cancellation
The price is CA $183 per night
CA $183
CA $203 total
Sep 1 - Sep 2
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.
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free cancellation
The price is CA $134 per night
CA $134
CA $146 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $428 per night
CA $428
CA $473 total
Aug 30 - Aug 31
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 Maine Mall and Casco Bay Lines Ferry Terminal are located nearby.
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $147 per night
CA $147
CA $163 total
Sep 7 - Sep 8
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.
Waves Oceanfront Resort

Waves Oceanfront Resort

3 out of 5
87 W Grand Ave Old Orchard Beach ME
The price is CA $266 per night
CA $266
CA $290 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Orchard Beach and Funtown Splashtown USA are located nearby.
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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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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 $1,008. 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.

Photos of local treasures

Browse Windham vacation photos for more inspiration

A lake surrounded by houses and trees with autumn foliage.
A white church with a steeple and red accents, surrounded by autumn trees.
A residential street with houses, autumn foliage, and parked cars.
A welcome sign to Windham, founded 1737, with a logo for Windham Eagles.
A road with directional signs for Route 202 East and Route 4 North, surrounded by autumn foliage.