Windham Holiday Rentals

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Holiday Rentals in Windham

Property grounds
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.4 out of 10, Very good, (21)
"The house was really great - plenty of room and a nice and serene. Older house with squeaky and uneven floors but the decor and some modern makeovers made it have great character! Communicating with property manager was very easy and we got prompt responses. The only thing worth mentioning that needs attention is the little bridge to go over to get to the driveway. Luckily we have a higher car but anyone with a regular sedan would have bottomed out and/or possibly got stuck. I’m sure it was...
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Private kitchen
2 duplex
3.0 star property
The price is HK$1,965
per night
25 May - 26 May
2 duplex
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (74)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
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Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (174)
"Even with a snow/ice storm, the beach doesn’t disappoint! Beautiful sunrises, sunsets, and waves crashing. The condo was warm and cozy and I was very happy to be able to watch the Bruins on tv. Already planned my next visit!"
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Aerial view
Everybody's favorite Maine beach location
9.2 out of 10, Wonderful, (12)
"The property was updated and very clean. The pillows were not very good, but the bed was great! The location was not where we anticipated. It was very easy checking in and out."
Everybody's favorite Maine beach location
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (16)
"This was a great spot for a weekend away! The unit is well equipped with higher end finishes and furnishings which makes the u it well worth visiting. The roof deck was a lovely addition as well! We left on Sunday so was happy to be able to move the car close to the unit Saturday evening to make packing a breeze."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Beach nearby
Little Miss Cottages
2.5 star property
8.2 out of 10, Very good, (68)
"Perfect place for a family to stay for a fair price if you want to stay a few nights and tour around the rest of Maine. Beach was wonderful! "
Little Miss Cottages
Property grounds
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
Beach/ocean view
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (113)
"Property was hard to locate. Inside, was very nice and clean. View was a 10/10 & balcony 10/10. The noise of the bar was crazy and didnt stop till 2am. Funiture and pictures vibrating, and this was the 4th floor. Cant image going there with a family with kids. Unless I was going to party, probably wouldnt stay here again. PS front door knob desperately needs to be fixed."
The price is HK$2,302
per night
3 Jun - 4 Jun
Oceanfront Condo! Spectacular Views From Private Large Balcony
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.4 out of 10, Exceptional, (16)
"The cottage was clean and accurately described. It was perfect for our needs and we are already looking forward to staying there again in the future."
The price is HK$1,170
per night
22 May - 23 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior
Relaxing loft style cabin getaway for 2. relax and enjoy!
10.0 out of 10, Exceptional, (273)
"This place is perfect for couples! Private, romantic and outdoor lovers dream! I cannot say enough! The pond is gorgeous and fishing access is wonderful! If the place comes up for sale we'll buy it!"
Relaxing loft style cabin getaway for 2. relax and enjoy!
Property grounds
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, (32)
"I rated this property a 4 and not lower because of its location. It is front-facing to the ocean, and that is always a gem in my book. Sleeping to the sound of the waves is amazing. The property management (Vacasa) was flawless in their communication and the housekeeping staff did a great job cleaning what they were responsible for cleaning. BUT....... this unit is in dire need of some deep cleaning and at a minimum some TLC in painting and in fixing what doesn't work (i.e., windows, toilet...
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Beach nearby
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, (22)
"Great place to stay"
The price is HK$741
per night
22 May - 23 May
2 min walk to the beach. Pet friendly condo
2 bedrooms, cots/infant beds, Internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.0 out of 10, Good, (6)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Property grounds
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
9.6 out of 10, Exceptional, (10)
"This place is just as nice as it looks in the pictures! My friends and I had a blast! What we appreciated the most was how communicative Jason was with us, and how welcome he made us feel! 10/10 recommend. Awesome place! :)"
The price is HK$2,893
per night
2 Jun - 3 Jun
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is HK$2,230
per night
27 May - 28 May
Glorious getaway on Portland's Eastern Promenade.
3 bedrooms, desk, iron/ironing board, travel cot
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (35)
"The cottage was very nice but the write-up was a little misleading. For example ocean views are very limited—mostly see rooftops, half bath was on ground floor, and stairs to main living area."
The price is HK$2,730
per night
6 Jun - 7 Jun
Beach House ∆ Prime Location ∆ Steps to the Ocean
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is HK$1,575
per night
2 Jun - 3 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
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See all available properties in Windham
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.

Other types of properties in Windham you may be interested in

Exterior
Microtel Inn & Suites By Wyndham Windham
3.0 star property
8.8 out of 10, Excellent, (1001)
"Nice hotel, good pool,common areas and outside, there was a rather large brown stain on the side of one of the mattresses in our room."
The price is HK$1,256
per night
30 May - 31 May
Microtel Inn & Suites By Wyndham Windham
Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1059)
"Always great! Sad about her lavender roll on missing this stay. Love that. Barbara was great at check in!!"
The price is HK$1,295
per night
2 Jun - 3 Jun
The Westin Portland Harborview
Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1200)
"I / we have stayed at the Portland Harbor Hotel at least 40 times over the years. I'm in the music business and one of the most talented "mastering" engineers on the planet (for LPs), Bob Ludwig, had his business here in Portland for decades. My assistant of also 40 + years lives near Portland and we always get together for dinner at Fore Street... a short walk from the hotel. The front desk people were very kind to put us in room 250 which is spectacular. You could swim laps in the...
The price is HK$1,787
per night
27 May - 28 May
Portland Harbor Hotel
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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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?

Rent a room in the gorgeous Holt House: This holiday home rental outside of Windham has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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?

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 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.

Recent reviews of Windham properties
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

5/5 Excellent
"Shower head in room 403 needs a wench. Was spraying water from around pipe"
A verified traveller stayed at La Quinta Inn & Suites by Wyndham Portland
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Portland