Windham Holidays

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Top hotels in Windham

The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$199 per night from 26 May to 27 May
S$199
includes taxes & fees
26 May - 27 May
8.8/10 Excellent! (1,001 reviews)
"Lovely hotel for those who wish to be removed from the hustle of the Old Port. Friendly, clean, new and upscale facility. This area of Portland is a bit gritty--not at all dangerous Bar at the top of the building is very good with wonderful views."

Reviewed on 22 Apr, 2025

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$296 per night from 4 May to 5 May
S$296
includes taxes & fees
4 May - 5 May
9/10 Wonderful! (1,482 reviews)
"Great location and nice room"

Reviewed on 25 Apr, 2025

Portland Harbor Hotel
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 S$122 per night from 1 May to 2 May
S$122
includes taxes & fees
1 May - 2 May
7.8/10 Good! (1,004 reviews)
"Love the pool"

Reviewed on 25 Apr, 2025

Clarion Hotel Portland
See all 3,189 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.

Frequently asked questions

How much does a Windham holiday package cost?
Offering great value package deals on Expedia, you’ll be surprised at how little a holiday to Windham costs! Expedia’s packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Windham?
If you’re looking to snag a cheap Windham holiday package, consider visiting in January, February and November. You’ll generally find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Windham?
With a well-organised travel plan, you can easily hit the most popular Windham attractions in a few days. But if you prefer to discover hidden spots or go on day trips, consider booking your Windham holiday for longer.
How to find the best Windham package deals?
Start your search for a Windham package deal by entering your preferred trip dates and destination under our “Packages” tab. Then add a few filters, like “Property type” and “Guest rating,” to tailor the results to your exact style. You can also sort by “Package discount” and discover offers that come with big savings. If you don’t find the ideal Windham package deal right away, just play around with 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 underway.
Is it cheaper to book a Windham holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalise your Windham getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Windham?
If you have your Windham travel dates finalized, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Windham?

  1. Pick your dates: What you’d like to do in Windham and your favourite season can help you decide when to travel.
  2. Set your budget: Factor in expenses like food, flights and transportation when calculating how much to put aside for your trip to Windham. Then, pick a property that works with your budget, whether that’s a low-cost option or a deluxe retreat.
  3. Decide how long to go away for: Now that you know more about Windham, you can work out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodation and airfare: Once you’ve nailed down your travel dates and duration, lock in the perfect Windham holiday package for you.

What to do in Windham

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

S$14
per adult
Downtown Golden Adventure Quest Experience in Portland
Portland Scavenger Hunt: The Maine Event

Self-Guided Portland Scavenger Hunt: The Maine Event

S$16
per adult
Self-Guided Portland Scavenger Hunt: The Maine Event
Old Wharf Street Portland, ME

Audio Guided Walking Tour from Old Port of Portland, Maine

S$10
per adult
Audio Guided Walking Tour from Old Port of Portland, Maine
See all activities in Windham

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.