Windham Holidays from £777

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Your Windham Holiday

With plenty of highlights as well as some hidden gems, this city is best experienced with a Windham holiday 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 holiday to Windham today.

Top Windham Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Freeport Hotel, Ascend Hotel Collection

The Freeport Hotel, Ascend Hotel Collection

2 out of 5
per person
18 Sept - 25 Sept
found 13 hours ago
Return direct flight included
London (LON) to Portland (PWM)
8/10 Very Good! (1,003 reviews)
The staff was friendly, professional and caring. I had ordered flowers for my girlfriend and the staff placed them in the room to ensure the surprise.

Reviewed on 1 Aug 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
per person
18 Sept - 25 Sept
found 13 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9.4/10 Exceptional! (591 reviews)
The breakfast each more was varied and delicious. There are bikes on the property which are great to ride around town

Reviewed on 29 Jul 2025

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
per person
18 Sept - 25 Sept
found 13 hours ago
Return direct flight included
London (LON) to Portland (PWM)
8.8/10 Excellent! (856 reviews)
Clean room, close to great restaurants and beaches. Nice warm pool and a lovely view!

Reviewed on 1 Aug 2025

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
18 Sept - 25 Sept
found 13 hours ago
Return direct flight included
London (LON) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Great option to explore Portland.

Reviewed on 3 Aug 2025

AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
per person
18 Sept - 25 Sept
found 13 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9.4/10 Exceptional! (182 reviews)
Mediocre property. Just another Lark property bought up by a private equity that owns most of the B and B’s in Maine. They destroyed what was once wonderful places to stay with all of their properties. The breakfasts used to take care and passion for cooking. Now they all serve the same continental food. Eh. I need to stop staying in Kennebunkport, even for the one night before heading north.

Reviewed on 28 Jul 2025

Windham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
State Theatre, East End Beach and Portland Museum of Art

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 £190 per night from 13 Aug to 14 Aug
£190
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Bed a little lumpy. Otherwise perfect... great location!"

Reviewed on 31 Jul 2025

Dormir
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 £127 per night from 11 Aug to 12 Aug
£127
11 Aug - 12 Aug
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Room was clean and bed was comfy; the bathroom sink gargled periodically, waking me in the night. Grab-n-go breakfast was listed on expedia but that isn't offered every day. Friendly and helpful staff"

Reviewed on 2 Aug 2025

Clarion Hotel Portland
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 £90 per night from 24 Aug to 25 Aug
£90
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,110 reviews)
"I enjoyed my stay and thought was excellent value for the money. For old property it has been kept up well. I enjoyed they had pool and strong AC in the rooms."

Reviewed on 3 Aug 2025

Days Inn by Wyndham Airport/Maine Mall
See all 3,326 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Windham

Port City Light Cruise

Port City Lights Cruise

£29
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

£51
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

£51
per adult
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks
See all activities in Windham

Frequently asked questions

Why should I book my Windham holiday with Expedia?
Expedia has your back for every aspect of your next Windham holiday. You'll always land the best deal possible, but when you bundle your airfares, accommodation and/or hire car into a holiday package, you'll get even bigger savings. Looking to truly make the most of your stay? Add some activities and tours to your customised package. Expedia offers flexible cancellation policies on most bookings, so you won't need to stress if your plans change. Visit our Customer Service Portal link to find out more.
When is the best time of year to holiday in Windham?
Peak season falls in January, April and December and is an exciting time to visit — if you don't mind the crowds. June, July and October are typically quieter times of the year. With daytime average temperatures of -4ºC, January is the coolest month in Windham. The warmest time of year is July, when you can experience averages of 20ºC throughout the day. Whatever the weather, you'll find loads to keep you occupied here.
What is the top hotel for my holiday in Windham?
Create lasting memories in Windham by choosing Portland Harbour Hotel as your home base and gateway to fun and adventure.
How do I get a cheap holiday to Windham?
Combining your hotel and flight with Expedia won't just save valuable time — it'll save you a tidy sum too. A Windham holiday makes it easy to put together your ideal trip. With more than 400 airlines worldwide to select from, finding flights that fit your busy schedule won't be a problem. On top of that, we have over 321,000 properties globally to select from. Now that's choice! Whatever your budget, Expedia will help show you the world. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Windham holiday?
Offering must-visit attractions such as University of Southern Maine and Maine Mall, a holiday in Windham is filled with exciting things to see and do. Thompsons Point and University of New England are two other sights also worth a look.
What is the best area to stay in when on holiday in Windham?
Windham has a number of popular places to explore, including Seacoast Adventure. Book a stay close by and make sightseeing stress-free.
Do I need a visa for my Windham holiday?
Visa requirements for Windham vary based on your nationality and purpose of your visit. We recommend checking official government websites to determine if you need a visa for your holiday. This is also a good place to find the most up-to-date information, including details about application procedures or any supporting documentation that may be necessary. Enquire about your visa requirements well in advance to ensure a smooth travel experience. Also double-check to see that your passport has a minimum of six months validity from your planned date of return.
What should I wear on my Windham holiday?
Though everyone's personal style varies, it can help to have some guidelines for what to wear on your holiday in Windham. We recommend browsing style blogs before you head off so you can blend in like a local. Be sure to look at the weather forecast so you can pack appropriately. The warmest month in Windham is July, with average daytime temperatures of 20ºC. If you plan to visit in the coolest month of January, the mercury hovers around -4ºC during the day.
What does an Expedia Windham holiday include?
Expedia has all you need to organise your Windham trip, but what goes into your package is up to you. Select from a combination of hotels, flights and hire cars. Searching for some experiences or tours to keep you busy? Once you've made your booking, you can add them on too. No matter your budget or style, there's a holiday package to meet your needs. Explore a wide range of property types and select one that fits your group size. The most sought-after rentals here are private holiday homes and cottages. With Expedia, it's easy to tailor your Windham escape the way you like.
Does Expedia offer Book Now, Pay Later Windham holidays?
We certainly do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan best suited to your needs during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable payment plans. If paying across multiple transactions sounds right for you, choose this option at checkout.
  • No-deposit holidays: If not paying ahead of time for your getaway makes clicking that "book now" button more stress-free, consider a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Windham Expedia holiday?
You can. We have more than 400 partner airlines across the globe, so fly with the carrier that's a good fit for your needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.