A white church with a steeple and red accents, surrounded by autumn trees.

Windham Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windham holiday rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (122 reviews)
"Really nice room and location"
United States
Victoria
The price is AU$661
includes taxes & fees
25 Oct - 26 Oct
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (13 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is AU$973
includes taxes & fees
27 Oct - 28 Oct
Evalina Hotel
A gravel patio with a table and chairs, surrounded by tall trees and a view of the water.

3. Placyd Pines Limit 8 4 Bedroom Cottage by RedAwning

Placyd Pines Limit 8 4 Bedroom Cottage by RedAwning
3.0 star property
Sebago
The price is AU$1,604
includes taxes & fees
14 Oct - 15 Oct
Placyd Pines Limit 8 4 Bedroom Cottage by RedAwning
A spacious living room with large windows, a sofa, a chair, and a small table.

4. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is AU$386
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Maine Street! Mcm-style Home in Brunswick
A living room with a gray sofa, a wooden coffee table, a ceiling fan, and a standing heater.

5. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is AU$480
includes taxes & fees
28 Sept - 29 Sept
1/2 Mi to Pier: Wfh-friendly Apt in Maine!

6. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is AU$404
includes taxes & fees
29 Sept - 30 Sept
'beachfront 9' Condo on Old Orchard Beach
A two-story house with a covered patio area featuring a table and chairs, a blue umbrella, and a 'Tenant Parking' sign.

7. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is AU$462
includes taxes & fees
29 Sept - 30 Sept
Walk to Pier & Ocean: Apt in Old Orchard Beach!
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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Top Windham Hotel Reviews

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

8/10 Good
"This was a nice place to stay, close to shopping and restaurants, although nothing within close walking distance. The room was large and comfortable. The only thing to be careful about is which side of the hotel you reserve a room in. One side faces a peaceful, quiet courtyard. The other side, where I was, faces a large, always busy, always noisy highway. I tried to change, even to an upgrade, but I couldn't. Pay the extra money for the courtyard."
Tom 2-night trip
Posted less than an hour ago
Fireside Inn & Suites Portland

Find out more about Windham

Everything you need to know about Windham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham holiday rentals we have selected for you start as low as AU$232 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals in Windham close to Seacoast Adventure, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffee shops during your trip.

What are some of the best holiday rentals that Windham has to offer?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Windham is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Windham?

Expedia has 37 holiday rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake Basin and Jordan Bay.

What are holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.