Windham Vacation Rentals

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Vacation 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
Comfort Duplex, 3 Bedrooms | Private kitchen
2 duplex
3.0 star property
The price is CA $345
CA $513 total
includes taxes & fees
May 29 - May 30
2 duplex
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (75)
"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)
"Excellent apartment in Old Port area of Portland. Bright, clean, updated, comfortable bed and furniture, lots of amenities. Would definitely stay there again!"
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, (114)
"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 CA $405
CA $648 total
includes taxes & fees
Jun 17 - Jun 18
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, (17)
"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 CA $246
CA $433 total
includes taxes & fees
Jun 10 - Jun 11
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior
MAY 31ST weekend open Book Wednesday/Thursday discounted rate!!!
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!"
MAY 31ST weekend open Book Wednesday/Thursday discounted rate!!!
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 CA $192
CA $376 total
includes taxes & fees
Jun 4 - Jun 5
2 min walk to the beach. Pet friendly condo
2 bedrooms, cribs/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 CA $461
CA $1,088 total
includes taxes & fees
Jun 2 - Jun 3
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 CA $393
CA $625 total
includes taxes & fees
May 27 - May 28
Glorious getaway on Portland's Eastern Promenade.
3 bedrooms, desk, iron/ironing board, travel crib
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 CA $378
CA $898 total
includes taxes & fees
May 30 - May 31
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 CA $277
CA $651 total
includes taxes & fees
Jun 2 - Jun 3
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!
Don't see what you're looking for?
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.

Windham Vacation Rental Travel Info

Number of vacation rentals
7
Popular accommodation
Windham private vacation homes
Known landmarks
Seacoast Adventure, Maine Wildlife Park and Southworth Planetarium
International airport
Portland, ME (PWM-Portland Intl. Jetport)

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, (1000)
"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 CA $221
CA $240 total
includes taxes & fees
May 29 - May 30
Microtel Inn & Suites By Wyndham Windham
Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1054)
"Excellent TV screen and easy channel options."
The price is CA $221
CA $251 total
includes taxes & fees
May 27 - May 28
The Westin Portland Harborview
Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1196)
"One of the best hotels we ever stayed in."
The price is CA $282
CA $360 total
includes taxes & fees
May 27 - May 28
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.

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windham vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham vacation rentals we have selected for you start as low as CA $192 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 vacation 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 vacation.

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 vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Maine Wildlife Park, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

Rent a room in the gorgeous Holt House: Located near Windham, this vacation home rental 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 vacation rentals are there in Windham?

Expedia has 32 vacation 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 vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

Recent reviews of Windham properties
Expedia verified reviews

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

5/5 Excellent
Very nice
"This stay was great. Room was clean and no lingering smell. Tv selection good. Bathroom was updated shiney and clean. Unfortunately I didn't have breakfast or get to test the pool. I would recommend and will return"
A verified traveller stayed at Ramada Plaza by Wyndham Portland
Posted 18 hours ago
Ramada Plaza by Wyndham Portland