Windham Holiday Rentals

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Holiday Rentals in Windham

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (84)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$425
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel
68 East Grand Ave
3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
United States
Benjamin
68 East Grand Ave
Bright and airy condo with beachfront access and walkable entertainment nearby
7.6 out of 10, Good, (4)
"Ease of beach access. "
United States
TAMMY K.
Bright and airy condo with beachfront access and walkable entertainment nearby
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (231)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
2.0 star property
10.0 out of 10, Exceptional, (5)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
United States
Tamerra J.
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
9.8 out of 10, Exceptional, (45)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Canada
Sebastien M.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
350 Yards to the beach. Pet friendly!
8.0 out of 10, Very good, (34)
"Bring your own linen if you plan on using pull out couch. Also it’s not a 2 bedroom but a 1 bedroom with full size pullout couch in sitting area which is good for kids only. You have to go through private bedroom to access bathroom. Only 1 Ac in the unit located in the private bedroom so if you close the door to the bedroom the sitting area does not get AC. "
United States
Jonnie Rose C.
The price is AU$682
includes taxes & fees
1 Nov - 2 Nov
350 Yards to the beach. Pet friendly!
Little Miss Cottages - Two Bedroom Cottage
10.0 out of 10, Exceptional, (1)
"Excellent place, so much fun!!!"
United States
Gregory D.
The price is AU$480
includes taxes & fees
2 Nov - 3 Nov
Little Miss Cottages - Two Bedroom Cottage
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (52)
"We loved everything about our stay here. Perfect location right on Old Orchard Beach. The house is perfect for what we needed/wanted. Wish we could have stayed longer. We would definitely come back for a longer stay next time we’re in Maine. "
United States
Chanmaly V.
The price is AU$754
includes taxes & fees
22 Oct - 23 Oct
Beach House ∆ Prime Location ∆ Steps to the Ocean
Romantic getaway for 2 PEAK fall foliage!!!
10.0 out of 10, Exceptional, (312)
"Peaceful and relaxing it was the perfect getaway"
United States
melissa d.
Romantic getaway for 2 PEAK fall foliage!!!
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
9.8 out of 10, Exceptional, (11)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
United States
Elizabeth h.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
10.0 out of 10, Exceptional, (39)
"An absolutely amazing week in Ocean Park. The Grey Goose is the perfect place for an extended family to enjoy the beach! "
United States
Mark W.
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
9.6 out of 10, Exceptional, (65)
"The views from this house are amazing. It is literally steps away from the beach. We had a family gathering with all ages and everyone had a great time. The house is spacious, clean and comfortable. The owner was very responsive when we reached out. We were able to see fireworks from the balcony as we were there during the 4th. It is close enough to walk to the pier area for the arcade/rides and restaurants. We loved our time in this home and hope to return again!"
United States
Jessica S.
The price is AU$1,936
includes taxes & fees
2 Nov - 3 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
10.0 out of 10, Exceptional, (99)
"Would love to stay here again!! "
United States
Michelle E.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Sebago Lake Cottage on Raymond Cape
10.0 out of 10, Exceptional, (48)
"Our family was up for a wedding so we came up to visit. This is a beautiful place. We will keep this in mind for the future. "
United States
Stacy C.
Sebago Lake Cottage on Raymond Cape
Lakefront Cottage: Boat Dock, Patio & Kayaks!
3.0 star property
Lakefront Cottage: Boat Dock, Patio & Kayaks!
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
9.6 out of 10, Exceptional, (12)
"Amazing off grid tiny house. Amazing views of the woods, fire pit, close to town. We are from Montana and gave stayed in some cool tiny homes but this the best one. Than you."
United States
Tyler M.
The price is AU$477
includes taxes & fees
23 Oct - 24 Oct
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (221)
"The Property had everything we needed to relax and have a great time."
United States
Christopher C.
The price is AU$531
includes taxes & fees
25 Oct - 26 Oct
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Direct Oceanfront/Beachfront Home in Saco, ME. Family Retreat sleeps 19 
9.8 out of 10, Exceptional, (40)
"Property was beautiful, large family we utilized all sleeping areas and had a wonderful stay. We arrived fairly early hoping to utilize the beach before entering seeing as we missed any traffic and the owner was very friendly and accommodating for us. Would definitely recommend for large groups looking for a relaxing stay. "
United States
Ashley J.
Direct Oceanfront/Beachfront Home in Saco, ME. Family Retreat sleeps 19 
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
2.0 star property
9.0 out of 10, Wonderful, (14)
"Very responsive host, even got us a pack and play for our youngest! Perfect house for a beach stay! Would stay again! "
United States
Matthew D.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
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 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$425 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?

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 31 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.