
House vacation rentals in Windham
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Top-rated house rentals in Windham
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Vacation rentals for every style
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Popular amenities for Windham house rentals
House rentals with a pool

Mountain Hideaway - Outdoor pool, hot tub
Great house. Host was responsive and helpful. House is very close to the mountain. We had 10 people in the house and there was plenty of room. Overall great stay.

Locke Lake Waterfront Escape
Me and my family had an awesome stay. The house was great with lots of space and places to sleep. We were 8 ppl and there was more than enough room. Garage/game room was awesome I just wish it was insulated with some heat we had to wear our coats to be comfortable, of course the weather was 26F so it was expected. The rest of the house was warm and cozy. I would love to rent this same house in the summer it must be amazing with the view of the lake. One more thing is although there are 2 bathrooms its more like 1 because the second bathroom upstairs has a little door that leads to the room with the 4 beds so the other people not staying in that room didn’t use that bathroom to not get walked in on unexpectedly. Overall I still gave this place 5 stars and it’s one of the best places I’ve stayed and the host is very responsive and accommodating.

Timber Ridge w/ Hot tub, Home Theatre
The scenery was beautiful and the house was the perfect size for our family. The kitchen was fantastic and the living room was very cozy with a nice fire place. The kids had plenty to do, we were able to spread out, and Susan was very nice to talk to and very responsive.

Walk to StoryLand!Updated Condo! WiFi/Golf/Pool/AC
Had a quick weekend getaway at Keith's place. Everything was perfect. Easy check in and great communication.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
We enjoyed our stay at Angela's. Communicative host, nice clean place, easy to find. Great for a weekend trip!

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage
Great place to stay. Winter months are definitely quiet, not a bad thing! I would stay here again.

Bear Brook House
Perfect location for our winter visit to North Conway area with 2 young kids! Close to skiing, restaurants, and attractions. Plenty of space for us and a well stocked kitchen so we could cook some meals at home.
Weekly house rentals

Opening late April !
Accomodations exactly as shown in pictures. Kitchen is definitely well equipped with all of the essentials and more. Ice cream shop right next door is great and The Lobster Pound on the other side is excellent. You can walk to shops and restaurants downtown but we had no problem finding parking in the evening so we could enjoy the awesome restaurants.

175 feet from Wells Beach! Sleeps 12 4 BR/3BA
Loved staying at Dustin's place. Easy going check in was a plus. The house was great, clean, easy to navigate. super hot water and great water pressure is always appreciated! The beach was so close, the arcade was walkable and or a quick bike ride. Having beach chairs available that I didn't have to pack up was a great add as well. We will definitely be back!-

90 second, traffic-free drive to Sunday River
Had a lovely stay! You have a beautiful home and so close to the slopes! We will definitely be back.

Sunday River - English Woods Chalet
What a wonderful stay my friends and I had for our annual ski trip to Sunday River! A perfect location that was calm and relaxing with plenty of space for four people! The sauna was an amazing amenity as well!!

Spacious 3 level family friendly home.Dog friendly
Tara was a great host, which any questions she got back to us with the answers almost immediately. The home was just as beautiful as the view and was a quick distance to the center of town. Fantastic place to gather with family for a cozy weekend in the woods. Most definitely will be staying with her listing again in the future!

North Conway 5 Bedrooms 3 Bath close to Downtown
Awesome place to stay and close to Cranmore. 5 min car ride was very convenient. There were some damages upon our arrival but everything was great. Recommended.

Hills Beach UNE 3-4 brs oceanview 50 steps 2 beach
We had a nice, quick Thanksgiving stay. Kimberly’s place was beautiful and comfortable.

Clean, private 3 bedroom home 1 mile from beach
Great spot with a lot of space you never feel like you are on top of each other. Gas station and restaurants within a 1 min drive. Grocery store 5 min drive.
Private house rentals

Beautiful, Peaceful, Maine Getaway House
This was our second time we have gone here for our anniversary. We love this place so much and so did our fur baby. We love that she is pet friendly

Beach Home w/ Exclusive privacy in Southern Maine
We had a wonderful time in Wells! An absolutely beautiful home with every amenity! Sharon was responsive, kind, and flexible with our stay. We enjoyed cooking and watching the Super Bowl in the amazing home theater! Do not miss out on this fantastic listing!

Oceanfront Luxury Estate in Mid-Coast Maine
This was such a wonderful property for my family -- beautiful and peaceful with lovely views. We loved spending our days out in the spacious yard, playing lawn games, sitting around the fire pit, and fishing, and eating all our meals out on the patio. Everyone left feeling very relaxed and happy. Thank you Pam and David for sharing your home!

Beautiful House to Relax & Enjoy the Quiet!
We had a wonderful stay. The house was very nice and all accommodations were met and exceeded. We cooked dinner in the kitchen two of the nights we were there and found everything we needed very easily. Everything was very clean and well taken care of, yet felt extremely homey and welcoming! The fire pit and outdoor bar were an amazing benefit, the whole back/front yards and patios in general were amazing. It’s safe to say we truly enjoyed our time in this home and will be checking here first next time we come! Highly recommended stay!

LUX Designer Private Waterfront
Was an outstanding mini vacation at Jon’s , hot tub was amazing, shower was awesome ! Very very cozy and nice little surprise in the fridge as well ! Over all very outstanding experience!

Updated 2 Bedroom Private House near beaches
We had a great stay in Tara's home. It is located in a quiet neighborhood and is close to our favorite towns- Ogunquit and Kennebunkport. We had plenty of room for the four of us. We loved the outside spaces and the open floor plan. Tara was very easy to communicate with and very responsive. The instructions for check in and check out were very clear. We hope to return in the future!

Newly Renovated House in York 4 Min Walk to Beach!
My college girlfriends and I wanted to get away for the weekend to somewhere cozy and peaceful. This is exactly what we found at Genevieve's place! In the freezing cold of a Northeast winter, we found warmth and comfort in this home. All spaces were clean and stocked with essentials. The provided space heater was put to good use as the snow fell outside, creating a magical atmosphere. Speaking of magic - the quick walk to the beach was a DREAM in the snow. It felt like we were wandering through a winter wonderland, to be greeted by the vast ocean on the other end. Genevieve was super helpful and responsive to all our needs and some unforeseen winter surprises. Everything was managed efficiently and promptly. I look forward to returning again in the future!

All Season Wells Beach Retreat attractions close
This is the second time I’ve stayed at this house. Spacious and a lot of light. You can see the marsh from the windows, which is lovely. Near the beach. Recommend!
Quick stats about house rentals in Windham
Total rentals
90 properties
Nightly prices starting at
$85 CAD before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Wells Beach
- Attitash Mountain Resort
- Cranmore Mountain Resort
- Story Land
- Ogunquit Playhouse
- Long Beach
- East End Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Mt. Abram
- Long Sands Beach
- King Pine Ski Area
- Purity Spring Resort
- Popham Beach State Park
- Ferry Beach
- Portland Country Club
- York Golf & Tennis Club
- Ledges Golf Club
- Powderhouse Hill Ski Area
- Lake Winnipesaukee Golf Club
- PowderHouse Hill
- Bald Peak Colony Club
- White Lake State Park