House holiday rentals in Windham

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Popular amenities for Windham house rentals

House rentals with a pool

Superhost
Home in Barnstead
4.84 out of 5 average rating, 101 reviews

Locke Lake Ski & Swim Escape

AmandaRating, 5 stars3 months ago
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.
Superhost
Home in Newry
4.79 out of 5 average rating, 133 reviews

Timber Ridge w/ Hot tub, Home Theatre

RichardRating, 5 stars3 months ago
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.
Superhost
Home in Bartlett
4.82 out of 5 average rating, 119 reviews

Walk to StoryLand!Updated Condo! WiFi/Golf/Pool/AC

VivianRating, 5 stars2 months ago
Keith’s townhouse was lovely. We had a wonderful stay. The unit was spotless and had everything we needed. Thank you for a great stay. Joe and Vivian
Superhost
Home in Portland
4.96 out of 5 average rating, 116 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

CoryRating, 5 stars5 days ago
Great house just a few minutes from downtown. The house was very cozy and clean in a quiet neighborhood. Our dogs loved the huge side yard as well. The heated ceiling fan in the upstairs bathroom is heavenly 😅
Superhost
Home in Portland
4.82 out of 5 average rating, 109 reviews

There's No Place Like Home

JeremyRating, 5 stars5 months ago
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!
Superhost
Home in Barnstead
4.89 out of 5 average rating, 120 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

MicheleRating, 5 stars1 month ago
Great place to stay. Winter months are definitely quiet, not a bad thing! I would stay here again.
Superhost
Home in Bartlett
4.87 out of 5 average rating, 99 reviews

Bear Brook House

MikeRating, 5 stars4 weeks ago
The house was perfect for a ski weekend with Attitash being 3 minutes down the road.
Superhost
Home in Arundel
5 out of 5 average rating, 10 reviews

Heated Pool! Gorgeous Home Close to Kennebunkport

ChrisRating, 5 stars6 months ago
We had a great weeklong stay at the house. There was plenty of space both inside and out for us to dine, play and relax. We were 8 people across three generations and everyone enjoyed the house itself as well as the heated pool, BBQ and fire pit. Great location as it was 10 minutes into Kennebunkport and even less to a large supermarket in Kennebunk. We would definitely be more than happy to return in the future.

Weekly house rentals

Guest favourite
Home in Ogunquit
4.95 out of 5 average rating, 73 reviews

Opening late April !

MaryRating, 5 stars4 months ago
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.
Guest favourite
Home in Newry
5 out of 5 average rating, 20 reviews

90 second, traffic-free drive to Sunday River

MeghanRating, 5 stars3 weeks ago
Great spot for a ski weekend at Sunday River! Lovely home with nice attention to detail and amenities!
Superhost
Home in Bethel
4.85 out of 5 average rating, 170 reviews

Sunday River - English Woods Chalet

CameronRating, 5 stars4 weeks ago
Everything was perfect at this place, it’s too bad that the hot tub didn’t work!
Guest favourite
Home in Intervale
4.97 out of 5 average rating, 178 reviews

Spacious 3 level family friendly home.Dog friendly

BrookeRating, 5 stars4 weeks ago
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!
Guest favourite
Home in Conway
4.85 out of 5 average rating, 111 reviews

North Conway 5 Bedrooms 3 Bath close to Downtown

JanelleRating, 5 stars1 month ago
We were an extended family on a ski getaway. The location was great, close to downtown and Cranmore Mountain. The house was clean, set up was great plenty of room and the owners were very responsive and accommodating. The owners went above and beyond when we had car trouble on the day of checkout. I would absolutely recommend them for your next stay.
Guest favourite
Home in Biddeford
4.98 out of 5 average rating, 52 reviews

Hills Beach UNE 3-4 brs oceanview 50 steps 2 beach

AndrewRating, 5 stars3 months ago
We had a nice, quick Thanksgiving stay. Kimberly’s place was beautiful and comfortable.
Guest favourite
Home in Old Orchard Beach
4.87 out of 5 average rating, 159 reviews

Clean, private 3 bedroom home 1 mile from beach

ThomasRating, 5 stars4 months ago
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.
Guest favourite
Home in Conway
5 out of 5 average rating, 12 reviews

S’No Problem | Spacious 3br | Near Skiing & Dining

SusanRating, 5 stars3 months ago
We visited for our annual girls shopping weekend. 7 of us ranging in age from 20-88! We love the Stonehurst Manor and have stayed in several of the different condos on property. The lay out of the condos is ideal for a bigger group. Tracey’s unit was perfect for us. The furniture was very comfortable, we loved the gas fireplace and we had every glass, plate, utensil etc.. at our fingertips. Easy check in and check out. Would definitely stay again! Thank you for sharing your home.

Private house rentals

Guest favourite
Home in Lebanon
4.97 out of 5 average rating, 337 reviews

Beautiful, Peaceful, Maine Getaway House

KristinRating, 5 stars6 days ago
Great house for a quick get away! Well equipped kitchen and very clean overall throughout the house. Great yard, and semi private, away from the other homes. We enjoyed our stay very much. Thank you!
Guest favourite
Home in Wells
4.99 out of 5 average rating, 78 reviews

Beach Home w/ Exclusive privacy in Southern Maine

JordanRating, 5 stars3 weeks ago
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!
Superhost
Home in Harpswell
5 out of 5 average rating, 36 reviews

Oceanfront Luxury Estate in Mid-Coast Maine

SharonRating, 5 stars5 months ago
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!
Guest favourite
Home in Wells
4.94 out of 5 average rating, 72 reviews

Beautiful House to Relax & Enjoy the Quiet!

NinoRating, 5 stars5 months ago
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!
Guest favourite
Home in Naples
4.99 out of 5 average rating, 108 reviews

LUX Designer Private Waterfront

AdinaRating, 5 stars2 weeks ago
Beautiful and secluded place, was very clean and communication was great. Would definitely come again
Guest favourite
Home in Wells
5 out of 5 average rating, 26 reviews

Updated 2 Bedroom Private House near beaches

AnnemarieRating, 5 stars4 months ago
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!
Guest favourite
Home in York
4.92 out of 5 average rating, 13 reviews

Newly Renovated House in York 4 Min Walk to Beach!

RizwanaRating, 5 stars4 weeks ago
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!
Superhost
Home in Wells
4.65 out of 5 average rating, 37 reviews

All Season Wells Beach Retreat attractions close

KarenRating, 5 stars4 months ago
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

    $96 AUD 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Windham
  6. House rentals