Windham Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Windham

Spacious Studio Near Sebago Lake

2.0 star property
Windham
10.0 out of 10, Exceptional, (2)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is AU$187
includes taxes & fees
9 Dec - 10 Dec
Spacious Studio Near Sebago Lake

Serene 1-bedroom house in Windham with Babbling Brook

Windham
Serene 1-bedroom house in Windham with Babbling Brook

Pine Point Beach private, quaint, charming studio.

2.0 star property
Scarborough
10.0 out of 10, Exceptional, (24)
"Sweet place! "
United States
Lisa G.
The price is AU$304
includes taxes & fees
9 Dec - 10 Dec
Pine Point Beach private, quaint, charming studio.

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is AU$243
includes taxes & fees
9 Dec - 10 Dec
The Outlet Studio, Rustic Comfort w Fireplace

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is AU$299
includes taxes & fees
17 Dec - 18 Dec
Sunny Spot with Private Parking.

Beautiful 1st Floor Apartment & Amazing Shower

Parkside
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AU$224
includes taxes & fees
9 Dec - 10 Dec
Beautiful 1st Floor Apartment & Amazing Shower

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
The price is AU$248
includes taxes & fees
9 Dec - 10 Dec
Adorable Portland getaway on the Eastern Promenade

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Old Orchard Beach
8.0 out of 10, Very good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is AU$328
includes taxes & fees
15 Dec - 16 Dec
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Peaceful & minutes from the Old Port with private parking

Knightville
9.8 out of 10, Exceptional, (7)
"Super Cute little apartment! My only complaint, is the parking. It gets a little tight. And the bed is a little firm for my liking, but overall it was super nice and convenient!"
United States
Samantha
The price is AU$296
includes taxes & fees
9 Dec - 10 Dec
Peaceful & minutes from the Old Port with private parking

Welcome to our BoHo Treehouse!

2.0 star property
Saco
10.0 out of 10, Exceptional, (8)
"Was blown away by the charm, decor and how welcoming the property was. Peaceful, quiet, clean. Will be returning at some point in the future!"
United States
Robert H.
The price is AU$433
includes taxes & fees
9 Dec - 10 Dec
Welcome to our BoHo Treehouse!

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is AU$332
includes taxes & fees
15 Dec - 16 Dec
Modern, Luxurious Cabin in the Woods - 03

City Amenities, Casco Bay Sunrises and Natural Beauty

East Deering
9.8 out of 10, Exceptional, (122)
"I loved staying in the vacation rental! There was a lot of space, a nice waterfront view, and it was convenient to get in/out of town. "
United States
Jade G.
The price is AU$390
includes taxes & fees
9 Dec - 10 Dec
City Amenities, Casco Bay Sunrises and Natural Beauty

Waterfront Access with Kayaks, Private Deck and a Firepit

2.0 star property
Gray
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is AU$1,110
includes taxes & fees
9 Dec - 10 Dec
Waterfront Access with Kayaks, Private Deck and a Firepit

In-town no frills 2 bedroom apt

West Bayside
8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is AU$238
includes taxes & fees
14 Dec - 15 Dec
In-town no frills 2 bedroom apt

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick
8.8 out of 10, Excellent, (23)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is AU$581
includes taxes & fees
10 Dec - 11 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill
9.8 out of 10, Exceptional, (171)
"Great location, clean and cute."
United States
Erin M.
The price is AU$388
includes taxes & fees
14 Dec - 15 Dec
Glorious getaway on Portland's Eastern Promenade.

Arlie`s Digs! - One Block To Willard Beach!

Willard Beach
10.0 out of 10, Exceptional, (61)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is AU$463
includes taxes & fees
9 Dec - 10 Dec
Arlie`s Digs! - One Block To Willard Beach!

Charming Studio apartment with WiFi, AC in welcoming Portland

Munjoy Hill
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is AU$323
includes taxes & fees
9 Dec - 10 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Saco
10.0 out of 10, Exceptional, (15)
"The property was exactly as advertised, and it was a perfect two night stay for us on a road trip up the Maine coast with our dogs. The location was perfect to explore Portland, Saco, Biddeford, and Kennebunkport. The hosts were super responsive and friendly. We would definitely stay here again in future!"
United States
Ryan S.
The price is AU$430
includes taxes & fees
9 Dec - 10 Dec
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Upscale Spacious OOB Beach House - Seasonal Heated Pool

Old Orchard Beach
10.0 out of 10, Exceptional, (11)
"We had a good stay. We enjoyed the home, it was clean, the housekeeper was there when we arrived though. I wish it was more lighting downstairs. Very quiet area. "
United States
Mika C.
The price is AU$721
includes taxes & fees
9 Dec - 10 Dec
Upscale Spacious OOB Beach House - Seasonal Heated Pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews

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$206 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?

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!: This holiday home rental outside of Windham is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

Expedia has 33 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.