Name: Portland Regency Hotel & Spa
Price range: CA $309
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.

Saco Bay Hotel

CA $1,093

per person

Aug 3 - Aug 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

7.6/10 Good! (1,051 reviews)

We just had a night stay there during a journey but it was comfortable and what we needed

Reviewed on May 7, 2026

The Weldon Hotel

Downtown Portland

CA $1,858

per person

Aug 3 - Aug 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

1802 House Bed and Breakfast

CA $1,347

per person

Jun 18 - Jun 20

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Portland (PWM)

9.6/10 Exceptional! (104 reviews)

Great place to stay for a getaway. Breakfast is outstanding, hostess and her husband prepare fresh ingredients with three tasty courses. Rooms are well decorated, clean, bright and comfortable. We stayed there in 2001 and again in 2025. Our favorite in Kennebunk Port.

Reviewed on Oct 28, 2025

Ogunquit River Inn & Suites

CA $1,134

per person

Jun 18 - Jun 20

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The front desk was incredibly nice. They moved us closer to our family in another room without being asked. It was very appreciated, thank you.

Reviewed on May 3, 2026

Portland Harbor Hotel

Downtown Portland

CA $1,453

per person

Aug 3 - Aug 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,753 reviews)

Really enjoyed our stay. Staff was great as well!

Reviewed on May 8, 2026

Ready to book your vacation to Windham?

Choose your dates

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

CA $134

CA $148 total

May 10 - May 11

includes taxes & fees

8.6/10 Excellent! (2,232 reviews)

It said free self parking but when I got there I was charged for parking

Reviewed on May 9, 2026

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

CA $253

CA $333 total

May 25 - May 26

includes taxes & fees

9.4/10 Exceptional! (1,758 reviews)

Everything and everyone were excellent

Reviewed on May 8, 2026

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Fully refundableReserve now, pay when you stay

CA $309

CA $342 total

May 31 - Jun 1

includes taxes & fees

9.4/10 Exceptional! (1,642 reviews)

Very nice for pets!

Reviewed on May 7, 2026

See all 3,206 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.