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.
Inn at Diamond Cove
Price was CA $1,647, price is now CA $1,358 per person
CA $1,358
per person
Aug 3 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
it was very unique having to take a ferry over, shuttle by golf cart and bikes. late in season only 1 restaurant available. looking for peace and quiet- this it the place. lots to walk around and look at with the old fort there.
Reviewed on Sep 25, 2025
The Meadowmere Resort
Price was CA $2,812, price is now CA $2,111 per person
CA $2,111
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.
Reviewed on Jun 22, 2026
Ogunquit River Inn & Suites
Moody
Price was CA $2,382, price is now CA $1,814 per person
CA $1,814
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
The staff was excellent and the room immaculate. Our room had no balcony, which was disappointing. It would have been nice to have a small table and chairs in the room.
Reviewed on Jun 27, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,557, price is now CA $2,029 per person
CA $2,029
per person
Aug 24 - Aug 28
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,123, price is now CA $1,706 per person
CA $1,706
per person
Aug 24 - Aug 28
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.4/10 Exceptional! (1,786 reviews)
I was told I would get a text when my room was ready, I never did and while sitting in lobby hours later watched multiple guests get their rooms.
I was told as an Expedia VIP, there would be a bottle of wine waiting for me in my room. There was none.
The bed made a loud creaking noise every time I moved. Outlets next to the bed were very loose.
While the location was great; not worth the money
Reviewed on Jun 26, 2026
Windham Hotel Deals
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Jun 30 to Jul 1
CA $226
CA $250 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (2,194 reviews)
"The staff were very nice. I did find it odd that they charged a parking fee, given their location."
Reviewed on Jun 26, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $395 per night from Jul 5 to Jul 6
CA $395
CA $491 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,773 reviews)
"Iron broken. Construction outside."
Reviewed on Jun 26, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $355 per night from Jul 5 to Jul 6
CA $355
CA $432 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,251 reviews)
"The size of the room and proximity to Old Town were good. However, the view was to the office building next door and our room did not get cleaned while we were there for 2 nights. The room and average breakfast were too expensive for what we got."
Reviewed on Jun 27, 2026
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
What to do in Windham
Portland Smartphone Audio Tour: Self-Guided Drive
CA $24
per traveller
100% of travellers recommend
Portland Tall Ship Cruise on Casco Bay
CA $138
per adult
88% of travellers recommend
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- Maine Mall
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- Seashore Trolley Museum
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- Gooch's Beach
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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.
