Windham Holidays

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Windham Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
17 Oct - 22 Oct
found 1 day ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Perfect location to enjoy old port

Reviewed on 13 Aug, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
17 Oct - 22 Oct
found 1 day ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
Property is modern and clean and a great choice if staying more than one night. The 5:00 check in time is inconvenient and the additional rates for early check in are ridiculous. Our room was ready early even though the information given before check in stated early check in was not available, so we appreciated that. Bed was okay comfort-wise, but the pillows are awful. The biggest gripe I had was being woken by a very loud family with screaming kids well before 7:30 am on a day we looked forward to sleeping in. If this matters to you, the walls and floors are not very soundproof. This was a very unpleasant way to start the second day of a two-day trip. On a positive note, the staff was available via text and responded to our questions quickly and professionally. One suggestion-an exterior sign. The loft was hard to find, with only small signage on the entry doors which is not easily visible from the street. Overall we were happy and would stay again.

Reviewed on 11 Aug, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
per person
17 Oct - 22 Oct
found 1 day ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.8/10 Exceptional! (114 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!

Reviewed on 23 Jul, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
per person
17 Oct - 22 Oct
found 1 day ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (149 reviews)
Small bathroom. No safe. No storage space. Everything else was above average.

Reviewed on 16 Jul, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Save 100% on your flight
per person
17 Oct - 22 Oct
found 1 day ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
Good hotel in good location but not exceptional

Reviewed on 14 Aug, 2025

Top hotels in Windham

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is S$322 per night from 20 Aug to 21 Aug
S$322
20 Aug - 21 Aug
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Great for a quick stay, not for a long stay."

Reviewed on 9 Aug, 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 S$162 per night from 27 Aug to 28 Aug
S$162
27 Aug - 28 Aug
includes taxes & fees
7.8/10 Good! (1,157 reviews)
"Great value and location."

Reviewed on 12 Aug, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is S$136 per night from 25 Aug to 26 Aug
S$136
25 Aug - 26 Aug
includes taxes & fees
7.6/10 Good! (136 reviews)
"Good place."

Reviewed on 12 Aug, 2025

Germaine Inn South Portland
See all 3,269 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.

What to do in Windham

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

S$9
per adult
Downtown Golden Adventure Quest Experience in Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

S$86
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

S$72
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
See all activities in Windham

Frequently asked questions

How much does a Windham holiday package cost?
Offering great value package deals from S$1,610 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.

* 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.