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.
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

3 out of 5
Downtown Portland
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Portland (PWM)
8.8/10 Excellent! (1,281 reviews)
Standard Holiday Inn, but it was way overpriced when I was there.

Reviewed on Jul. 25, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The oceanview was breathtaking, the morning sun was stunning

Reviewed on Jul. 22, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Excellent in a great location

Reviewed on Jul. 26, 2025

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Portland (PWM)
8.8/10 Excellent! (1,153 reviews)
Great location and wonderful customer service! Really quiet in the room so you can hear quite a bit outside, shower pressure wasn't great but bed was comfortable and room was clean. There was some construction going on that we weren't aware of but it wasn't a deal breaker. Love that they offer airport shuttle!

Reviewed on Jul. 22, 2025

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
East Bayside
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Portland (PWM)
9.4/10 Exceptional! (953 reviews)
There wasn’t anything in particular about this property that I disliked.

Reviewed on Jul. 21, 2025

Ready to book your vacation to Windham?

 

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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 $316 per night from Jul 28 to Jul 29
CA $316
CA $345 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"I liked it! Thanks for a good stay"

Reviewed on Jul. 20, 2025

Dormir
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 24 to Aug 25
CA $150
CA $164 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,069 reviews)
Quiet, clean
"Good bed, clean, nice basic hotel. Only complaint was that the bathroom door stuck. There also was not much pressure for the cold water in the sink. Quiet even though it seemed full and was beside a busy road. Very close to the mall, dining, and turnpike."

Reviewed on Jul. 24, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Aug 11 to Aug 12
CA $208
CA $231 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,023 reviews)
"Excellent"

Reviewed on Jul. 23, 2025

Clarion Hotel Portland
See all 3,327 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.
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What to do in Windham

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $91
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

CA $77
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $49
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
See all activities in Windham

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $1,214 on Expedia for your Windham getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
You can generally find lower prices and greater availability in January, February and November. Take a look at our cheap Windham vacation packages and you could score some excellent off-season deals.
How many days is enough for Windham?
With a well-planned schedule, you can easily hit the main Windham sights in a few days. But if you prefer to venture off the beaten track or go on day trips, think about booking your Windham vacation for longer.
How to find the best Windham package deals?
Start your search for a Windham package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Windham package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windham adventure off to a flying start.
Is it cheaper to book a Windham vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Windham vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Windham?
If you have your Windham vacation dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Windham?

  1. Choose your dates: What you plan to do in Windham and your preferred season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Windham.
  3. Decide how long to go for: Now that you know more about Windham, you can work out the ideal length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Windham vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.