Windham Holiday Rentals

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Holiday Rentals in Windham

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.4 out of 10, Very good, (32)
"We would absolutely book this house again. Super peaceful location. Loons in the morning were a stellar start to each day. "
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (95)
"This beach home was clean and beautiful, it had everything we needed and was in a great location. We loved that it was right on the ocean, which meant amazing sun rises and easy access to walks on the beach. We were there in October, so there wasn’t much going on in Old Orchard beach, but that was okay with us! It was a quiet cozy town when we were there. There were plenty of other places to visit in the surrounding area!"
Gorgeous ocean-front home with stunning beach views
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (89)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is AU$319
includes taxes & fees
3 Nov - 4 Nov
Adorable Portland getaway on the Eastern Promenade
Sensational House on Sebago Lake, Raymond, ME
9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME
Romantic getaway for two Relax and enjoy Trickey pond early check in
10.0 out of 10, Exceptional, (290)
"We had the most amazing 48-hours! We will DEFINITELY be booking again with Dave!"
Romantic getaway for two Relax and enjoy Trickey pond early check in
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (34)
"Great place. Cool spot. Host was wonderful. Rooftop was awesome. Highly recommend!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (193)
"Great condo! We absolutely loved the patio that faces the water! Great location close to everything!"
The price is AU$528
includes taxes & fees
10 Nov - 11 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (120)
"Great central location for day trips, and then you get relaxing views and sounds of the ocean. There is music from the bar below, but it was a fun atmosphere and we found it enjoyable. "
The price is AU$528
includes taxes & fees
7 Nov - 8 Nov
Oceanfront Condo! Spectacular Views From Private Large Balcony
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"This property is exactly as it’s listed. Mr. Murphy is a kind and helpful host. The location can’t be beat. So close to anything you’d want to see and right on the beach. Watching the dogs play on the beach and the boats was a highlight. The view is so beautiful it looks fake lol. I truly hope to be back one day. "
Charming 110-year former Inn 10' from the Ocean!
Lakefront home with lovely lake views - one mile from the casino
9.8 out of 10, Exceptional, (39)
"Beautiful spot. Meticulous home. We are already talking about going back. "
Lakefront home with lovely lake views - one mile from the casino
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
10.0 out of 10, Exceptional, (136)
"We had a fabulous time. You would never know there was a town 2 miles from the house. It was very peaceful and welcoming. The cottage was very clean and had no issues what so ever. We were able to choose from quite a few events going on in the area and enjoy the fall foliage. "
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (139)
"Cute apartment. Construction was very distracting and noisy. TV buffers really bad. "
The price is AU$476
includes taxes & fees
4 Nov - 5 Nov
Glorious getaway on Portland's Eastern Promenade.
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
7.4 out of 10, Good, (26)
"The location was amazing! Walking distance to the pier, and right by the beach! We enjoyed that it was far enough down from the pier that the beach was a bit less crowded but we were still able to walk downtown. The accommodations are very cute and rustic. Some things could use attention, like paint touch ups and the patio table needs replacing… however these were minor issues and we will be back! "
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Beachfront cottage on Fortunes Rocks Beach
10.0 out of 10, Exceptional, (84)
"Everything about our trip was amazing! Tyler was extremely responsive, each and every time I reached out. This very cozy home is directly on the ocean and is exactly as described. Super clean, the BEST location, and of course it didn't hurt we had wonderful weather! Not that it would have mattered. It is evident the care and love that has gone into this longtime family home. And seriously, there is EVERYthing you could possible want or need for your stay. We felt right at home the minute we...
Beachfront cottage on Fortunes Rocks Beach
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (37)
"Very comfortable. Convenient very easy beach access."
The price is AU$872
includes taxes & fees
19 Nov - 20 Nov
Beach House ∆ Prime Location ∆ Steps to the Ocean
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (25)
"We had a wonderful visit to OOB to finish off our summer. The cottage is a quick walk to the beach and pier. It was very clean and comfortable for the four of us to relax and recharge in between swimming, playing mini-gold, and enjoying the amusement park."
The price is AU$375
includes taxes & fees
3 Dec - 4 Dec
Large 2BD cottage 10 min to Pier & Beach Pets ok
Little Miss Cottages
2.5 star property
8.4 out of 10, Very good, (82)
"Great location and cute cabins. We have been coming to OOB for years and this is the best pet friendly rental!"
Little Miss Cottages
100 feet from the ocean 3 bedroom cottage 420 friendly
8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
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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Other types of properties in Windham you may be interested in

Microtel Inn & Suites By Wyndham Windham
3.0 star property
8.8 out of 10, Excellent, (1010)
"Close to relatives"
The price is AU$168
includes taxes & fees
1 Dec - 2 Dec
Microtel Inn & Suites By Wyndham Windham
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.4 out of 10, Very good, (2327)
"The check in clerk was very good. We appreciated her help after a long day spent in an airplane. Great customer service!"
The price is AU$132
includes taxes & fees
16 Nov - 17 Nov
Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
4.0 star property
8.8 out of 10, Excellent, (1009)
"Great location and good service "
The price is AU$152
includes taxes & fees
1 Dec - 2 Dec
The Westin Portland Harborview
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.

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals in Windham close to Maine Wildlife Park, 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?

100' of Little Sebago Lake frontage: Enjoy the simple life & endless family fun!: This highly rated holiday home rental in Windham is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with 1 hot tub and a selection of books.

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?

Family-friendly attractions include Maine Wildlife Park and Seacoast Adventure, whereas Little Sebago Lake and Sebago Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Jordan Bay and Sebago Lake Basin.

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.