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.
Ogunquit River Inn & Suites
The Weldon Hotel
Saco Bay Hotel
Portland Harbor Hotel
Casco Bay Inn

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Windham Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from May 28 to May 29
CA $225
CA $245 total
May 28 - May 29
includes taxes & fees
8.8/10 Excellent! (999 reviews)
"Rooms were over priced, hot water for shower was limited, breakfast was average for this type of property."

Reviewed on May 19, 2026

Dormir
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is CA $295 per night from May 31 to Jun 1
CA $295
CA $380 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,768 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."

Reviewed on May 25, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is CA $255 per night from May 28 to May 29
CA $255
CA $282 total
May 28 - May 29
includes taxes & fees
9.4/10 Exceptional! (1,650 reviews)
"Just okay, guest services staff a bit aloof. Can’t beat the location in the heart of the old port. Comfortable bed. Room service closed too early. Nothing in the minibar fridge. Walls are surprisingly thin. I expected more from the Regency."

Reviewed on May 25, 2026

Portland Regency Hotel & Spa
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

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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.