Name: Portland Regency Hotel & Spa
Price range: CA $255
Rating: 9.4

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

CA $1,031

per person

Jul 22 - Jul 25

found 15 hours ago

Roundtrip flight included

Toronto (YTO) to Portland (PWM)

9/10 Wonderful! (1,003 reviews)

Great experience all around. Will definitely visit again if in the area.

Reviewed on May 25, 2026

The Weldon Hotel

Downtown Portland

CA $1,927

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.8/10 Exceptional! (101 reviews)

Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

Saco Bay Hotel

CA $1,272

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

7.6/10 Good! (1,054 reviews)

Rooms were clean. It’s a no frills hotel, but perfectly fine for a one night stop on the way to somewhere else.

Reviewed on May 24, 2026

Portland Harbor Hotel

Downtown Portland

CA $1,901

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (1,774 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

Casco Bay Inn

CA $1,735

per person

Aug 9 - Aug 16

found 24 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

8/10 Very Good! (1,005 reviews)

No coffee, no keurig, no continental breakfast amenities, and no warning that the place was under massive renovations.

Reviewed on May 18, 2026

Ready to book your vacation to Windham?

Choose your dates

Windham Hotel Deals

Dormir

965 Roosevelt Trail Windham ME

Fully refundableReserve now, pay when you stay

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

Portland Harbor Hotel

468 Fore Street Portland ME

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 Regency Hotel & Spa

20 Milk Street Portland ME

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

See all 3,242 properties in Windham

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.