North Windham Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your North Windham Vacation
Come and discover this wonderful city for yourself with a North Windham vacation package. Think about staying in the neighborhood of North Sebago, which is great for views and camping, and your time here will be nothing short of unforgettable. Make sure to do some sightseeing during your trip to North Windham. Seacoast Adventure and Maine Wildlife Park are some of the major places to visit. Stop dreaming and start doing. Browse the many options on Expedia today and finally put your North Windham vacation plans into motion!
Top North Windham Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
CA $1,548
per person
Oct 1 - Oct 4
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.8/10 Excellent! (202 reviews)
Our anniversary was ruined at the Inn at Diamond Cove!! We called in advance to have a golf cart available to take us to the resort and when we arrived there was no shuttle. We called the hotel again and 20 minutes later it arrived. We traveled to this location to enjoy the jacuzzi and the jacuzzi heater was broken. We tried to go to sleep at 11 p.m. and a noise was thudding above our heads for an hour. Then, the noise started again at 5 a.m. I called the front desk 6 times from the room phone and there was no answer!!! So, in pajamas I walked down to the front desk and the woman started screeching at me that she got my calls... but their phone system didn't work and I should have known that... and the noise was not her problem! I told her that a guest should not have to stumble out of bed to talk to the front desk and I asked for a refund, to which she agreed, I then emailed the hotel manager and they refused to give me any compensation!! DO NOT STAY AT THIS HOTEL!! They take no responsibility for a terrible guest experience and they STINK!!!!!
Reviewed on Aug 11, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $2,155
per person
Oct 1 - Oct 4
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (367 reviews)
Unexpectedly found The Docent's Collection on my trip wanting to spend an extra night. I was generously accommodated before my 4 pm check in time as I was already in the area. It is a beautiful loft style apartment/room that is spacious and very clean. Also within walking distance of a lot of the places I wanted to visit. I loved it so much and I would definitely be back soon.
Reviewed on Aug 9, 2026
Ready to book your vacation to North Windham?
North Windham Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $129
CA $141 total
Sep 10 - Sep 11
includes taxes & fees
7.2/10 Good! (665 reviews)
"Check in was very poor, took way too long and the line was very long. Property outside was overgrown with weeds and not very well kept. Rooms were ok for a cheap place to stop while traveling."
Reviewed on Aug 11, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $182
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very good! (1,626 reviews)
"If you are going to Thompson's Point, this is the place to stay. Easy to get to the point and back after the show. A reasonable walk into town or the hotel has a shuttle that you can reserve."
Reviewed on Aug 11, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $134
CA $146 total
Aug 18 - Aug 19
includes taxes & fees
6.4/10 (1,044 reviews)
"The room had a horrible smell. The door didn’t lock. There were holes in the wall covered in spackling."
Reviewed on Aug 11, 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.
What to do in North Windham
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
90% of travellers recommend
Morning Lighthouse Cruise Along the Coast of Portland Maine
CA $83
per adult
Frequently asked questions
How much does a North Windham vacation package cost?
You can grab a vacation package to this top destination from CA $1,301 on Expedia. But how much your vacation to North Windham costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to North Windham?
You're likely to find lower rates and better availability in January, February and March. Take a look at our cheap North Windham vacation packages and you could land some excellent off-season deals.
How many days is enough for North Windham?
Generally, a handful of days is enough to check out the main sights during your North Windham vacation. However, if you want to have time to unwind or go on day trips, think about extending your itinerary.
How to find the best North Windham package deals?
Use Expedia's filter tool to find some terrific North Windham package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for North Windham package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a North Windham vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your North Windham trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to North Windham?
If you're planning an impromptu North Windham getaway, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to North Windham?
- Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to visit North Windham.
- Set your budget: Factor in costs such as flights, meals and transportation when calculating how much to save for your trip to North Windham. Then, pick a hotel that matches your budget, whether that's an affordable option or a lavish retreat.
- Work out your trip length: Consider how much time you'd like to spend exploring North Windham. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a North 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.
