Windham Holiday Rentals

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Holiday Rentals in Windham

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.6 out of 10, Excellent, (35)
"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
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)
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
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (99)
"Property was as described, communication was easy and fast, property was clean, spacious, and felt homey. We will be back! "
The price is AU$812
includes taxes & fees
24 Nov - 25 Nov
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
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
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
9.6 out of 10, Exceptional, (26)
"Repeat visit. Short walk to beach. Convenient to stores if you want to shop. Cottage comfortable. We’ll be back!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Lakefront home with lovely lake views - one mile from the casino
9.8 out of 10, Exceptional, (41)
"This was the perfect location to get away for the weekend and celebrate my wife and I’s 10 year anniversary. The property was clean, private, and had great views being on the pond. The hot tub was an added bonus. I would definitely recommend this home and stay here again! "
Lakefront home with lovely lake views - one mile from the casino
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.
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (122)
"The condo was a little out dated but the balcony and the views of the sunrise can’t be beat!"
The price is AU$474
includes taxes & fees
26 Nov - 27 Nov
Oceanfront Condo! Spectacular Views From Private Large Balcony
Little Miss Cottages
2.5 star property
8.4 out of 10, Very good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
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
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
8.2 out of 10, Very good, (12)
"We enjoyed our brief stay"
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
9.0 out of 10, Wonderful, (27)
"Cute place - makes very good use of the space. It was comfortable and very conveniently located to everything we wanted to do. We have a few suggestions but overall very happy, had a wonderful time, and the ultimate compliment - we look forward to staying there again. "
The price is AU$595
includes taxes & fees
23 Nov - 24 Nov
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
9.0 out of 10, Wonderful, (2)
"Our stay at the property was great."
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is AU$474
includes taxes & fees
9 Dec - 10 Dec
Glorious getaway on Portland's Eastern Promenade.
2 duplex
3.5 star property
2.0 out of 10, (1)
2 duplex
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, (999)
"Nice stay overall"
The price is AU$169
includes taxes & fees
8 Dec - 9 Dec
Microtel Inn & Suites By Wyndham Windham
La Quinta Inn & Suites by Wyndham Portland
2.5 star property
9.0 out of 10, Wonderful, (2017)
"I enjoyed my stay, room was quiet, slept well 4 nights!!! Only downside was skimpy breakfast compared to la quinta in Harrisburg earlier on our trip."
The price is AU$140
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Portland
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.4 out of 10, Very good, (2375)
"Very good"
The price is AU$119
includes taxes & fees
22 Dec - 23 Dec
Casco Bay Hotel, Ascend Hotel Collection
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 28 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.