
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.

Ramada Plaza by Wyndham Portland
Nasons Corner
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,056 reviews)
I would have like to have the hotel provide a continental breakfast. There was a restaurant attached to the hotel called "Stacks" that was a rip off they charged me for the milk in my tea.
Reviewed on Aug. 7, 2025

Portland Harbor Hotel
Downtown Portland
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great option in Old Port. Very convenient to dining, shopping and boat tours. You can walk to everything. Courtyard was lovely in the evening for cocktails around the firepit. Would definitely recommend!
Reviewed on Aug. 7, 2025



Kennebunkport Captains Collection
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (598 reviews)
The breakfast each more was varied and delicious. There are bikes on the property which are great to ride around town
Reviewed on Jul. 29, 2025
Windham Hotel Deals

Dormir
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is CA $317 per night from Aug 13 to Aug 14
CA $317
CA $346 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"I like the cleanliness. I do wish that for the price, room cleaning/replenishing towels, was available. Currently have to bring dirty towels down, in order to get clean ones."
Reviewed on Aug. 5, 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 $160 per night from Aug 24 to Aug 25
CA $160
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,126 reviews)
Pleasantly surprised!
"After I booked the room, I started to read some of the reviews and instantly began to regret my decision. I didn’t have time to refund it so we took a chance. I’m glad we did! I’m not sure what all the fuss was about. I saw no bugs. I thoroughly checked. Albeit the room wasn’t immaculate. Housecleaning ..."
Reviewed on Aug. 6, 2025

Germaine Inn South Portland
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $147 per night from Aug 17 to Aug 18
CA $147
CA $160 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (117 reviews)
"They did not have my accessible room ready when I arrived at 3 pm. The WiFi setup was very clunky and only partial worked."
Reviewed on Aug. 2, 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
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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.