Windham Holiday Rentals

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Holiday Rentals in Windham

Spacious Studio Near Sebago Lake

2.0 star property
Windham
10.0 out of 10, Exceptional, (1)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is NZ$216
includes taxes & fees
14 Nov - 15 Nov
Spacious Studio Near Sebago Lake

Serene 1-bedroom house in Windham with Babbling Brook

Windham
Serene 1-bedroom house in Windham with Babbling Brook

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is NZ$488
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
The price is NZ$345
includes taxes & fees
16 Nov - 17 Nov
Sunny Spot with Private Parking.

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Old Orchard Beach
10.0 out of 10, Exceptional, (32)
"Great location and great host. "
United States
Dwight P.
The price is NZ$785
includes taxes & fees
30 Nov - 1 Dec
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

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

Old Orchard Beach
8.0 out of 10, Very good, (24)
"Cozy little cotrage"
United States
craig H.
The price is NZ$341
includes taxes & fees
17 Nov - 18 Nov
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

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 NZ$410
includes taxes & fees
3 Dec - 4 Dec
Modern, Luxurious Cabin in the Woods - 03

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
The price is NZ$290
includes taxes & fees
20 Nov - 21 Nov
The Outlet Studio, Rustic Comfort w Fireplace

Peaceful & minutes from the Old Port with private parking

Knightville
9.8 out of 10, Exceptional, (7)
"My husband and I had a wonderful weekend in South Portland and enjoyed the central location and charming touches of Jennifer’s apartment. The space is lovely, exactly as described in the listing. The communication was clear and detailed. We will definitely return!"
United States
Caitlin C.
The price is NZ$381
includes taxes & fees
17 Nov - 18 Nov
Peaceful & minutes from the Old Port with private parking

Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Auburn
9.6 out of 10, Exceptional, (8)
"The property was very clean and comfortable. The check-in process was easy given the very detailed instructions provided by the property manager ahead of time. We only stayed for one night while visiting family in the area, but would absolutely stay longer/come back again."
United States
Ashley S.
The price is NZ$604
includes taxes & fees
23 Nov - 24 Nov
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is NZ$335
includes taxes & fees
17 Nov - 18 Nov
Adorable Portland getaway on the Eastern Promenade

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

Brunswick
8.8 out of 10, Excellent, (23)
"Great location for baileys island and popham"
United States
Anonymous traveller
The price is NZ$707
includes taxes & fees
23 Nov - 24 Nov
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

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

Saco
10.0 out of 10, Exceptional, (13)
"perfect for a couple wanting something that is clean and cozy near beaches in Maine"
United States
Karalyn K.
The price is NZ$494
includes taxes & fees
17 Nov - 18 Nov
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Beach across the Street. Pets OK

Old Orchard Beach
8.6 out of 10, Excellent, (31)
"Perfect spot! Right near the beach and walking distance to all the best places. Very clean and chill little place perfect for what I was going for."
United States
Dom C.
Beach across the Street. Pets OK

Cheerful 1 bedroom cottage only 50ft from beach

Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"Amazing!"
Canada
Annie B.
The price is NZ$412
includes taxes & fees
16 Nov - 17 Nov
Cheerful 1 bedroom cottage only 50ft from beach

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

Willard Beach
10.0 out of 10, Exceptional, (60)
"Near beach, walking, bakery, ice cream and close to great restaurants. Lovely spot and easily accommodated 2 couples. Would stay here again!"
United States
Kirstin D.
The price is NZ$610
includes taxes & fees
2 Dec - 3 Dec
Arlie`s Digs! - One Block To Willard Beach!

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (24)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
The price is NZ$549
includes taxes & fees
29 Nov - 30 Nov
Serenity between the lakes and seashore

Bright & Sunny West End Apartment with Private Parking.

West End
10.0 out of 10, Exceptional, (45)
"Adorable apartment for our family of 5 to spend a night. Great location in town. "
United States
Brandy C.
Bright & Sunny West End Apartment with Private Parking.

Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Oakdale
10.0 out of 10, Exceptional, (43)
"Perfect accommodations! My best friend and I, along with my husband, had the best time. The beds were dreamy and the kitchen had all the supplies we needed. Quiet neighborhood within a 5 minute Uber to downtown- our first trip to Portland and we hope to be back soon!"
United States
Tara (Harris) K.
The price is NZ$554
includes taxes & fees
16 Nov - 17 Nov
Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Saco/Old Orchard Beach Get Away

2.0 star property
Saco
10.0 out of 10, Exceptional, (3)
"the apartment was perfect! It was clean and comfortable. Bed and pillows were great. Walking distance to some really sweet coffe shops. We fell in love with Swell! Thank you for being so patient with us as navigated some excited kids after long days of playing lacrosse! Great hosts!! "
United States
Jessica L.
The price is NZ$632
includes taxes & fees
14 Nov - 15 Nov
Saco/Old Orchard Beach Get Away
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

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 favorite 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 depends 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 NZ$247 per night. Entering your travel dates in the search wizard you might find 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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Windham is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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 32 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.