
Windham Vacation Packages
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Your Windham Vacation
With plenty of highlights as well as some hidden gems, this city is best experienced with a Windham vacation package. Book a hotel in Parkside, which is good for festivals, markets and walking. If your trip to Windham includes a little sightseeing, don't miss well-known attractions like Maine Wildlife Park, Riverside Municipal Golf Course and MAGAN Trailhead. Check out Expedia's wide range of travel options and begin planning your perfect vacation to Windham today.
Top Windham Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Portland Harbor Hotel
Downtown Portland
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Moderate luxury in the heart of everything Portland. Lots of shopping and dining in a short walk. The amenities fee is unusual.
Reviewed on Aug. 2, 2025

Blind Tiger Portland – Carleton Street
West End
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (114 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!
Reviewed on Jul. 23, 2025


The Docent's Collection
Downtown Portland
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (218 reviews)
Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.
Reviewed on Jul. 31, 2025
Windham Hotel Deals

Dormir
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from Aug 4 to Aug 5
CA $318
CA $347 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Bed a little lumpy. Otherwise perfect... great location!"
Reviewed on Jul. 31, 2025

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Aug 11 to Aug 12
CA $210
CA $232 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Breakfast food served out of a closet was a little odd, but it did taste good."
Reviewed on Aug. 1, 2025

Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,101 reviews)
"Outside wasn't well kept up. The room was average, clean."
Reviewed on Jul. 31, 2025
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.
What to do in Windham

Portland: Maine Lighthouses Sightseeing Cruise with Drinks
CA $95
per adult

Portland: Sightseeing Cruise to Portland Head Light
CA $49
per adult
98% of travellers recommend
Frequently asked questions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.