House holiday rentals in Windham

Great and relaxing location, close to local amenities. Perfect for small groups, Hillary was awesome to rent from.

We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

Had a quick weekend getaway at Keith's place. Everything was perfect. Easy check in and great communication.

Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

Great stay so homey and comfortable has everything we needed staying with two little girls ! Having laundry and kitchen made everything so convenient ! Close to so many things to do was the best vacation we’ve been on would definitely love to come back . Clean and organized everything was easy to find ! Great amenities pool ect !

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!

The house is beautiful and the views are just breathtaking. From inside the house, you get a beautiful view of the lake and then the porch is amazing. You can kayak, use the paddle board or use the canoe. You can also sit by the lake and enjoy the campfire. The surroundings are very beautiful and peaceful. The host is very responsive, solved all our doubts and was flexible with us during check-in and check-out, which we appreciated very much. At check-in, we were greeted by a great bottle of wine and chocolates, which was a great touch. The house also has a ping pong table, books to read and board games. The kitchen was well stocked with the basics. We had an amazing stay, we highly recommend this property :)

Great house! Very spacious, plenty of bathrooms, and fantastic location. Very easy to communicate with the owners and check in/out was simple. My minor only critique is that we wish the grill were a bit bigger and nicer. We wanted to grill one day, but we were a little disappointed and unable to do so due to the grill quality. Would definitely stay again!

Cute place. Perfect for our family of 4. Close to hiking and short walk to lake. The wifi was spotty but otherwise it was great.

We really enjoyed our stay in Windham. The house was exactly as described and it was not just dog friendly, it was dog accommodating (just like Portland). Would definitely stay again.

Although my son was disappointed that her cat Batman didn't come with our rental (wink;), this house exceeded our expectations! We visit Maine every summer because we have family there and typically stay with Aunt Jeanne. This time there was an abundance of family staying at her house towards the end of our vacation so we opted to get this beautiful Airbnb for the weekend. This house is BIG. Has a lovely deck with a great outside garden. We heard a family of Barred Owls at night! If you follow the path it opens up to this HUGE field with a (very clean and stylish) yurt and a fire pit. At night- the stars are AMAZING in this field. One thing that we now have to get back at home- a bidet. This trip was the first time we have tried one.... hahah!

This unit was delightful in every way...clearly a labor of love, solidly and tastefully built, such a well-stocked kitchen, terrific lighting, spotless, awesome spaces to hang out (screened-in porch, back deck, multiple places to sit and eat), very thoughtfully done! We enjoyed the firepit with all the fixings to get a fire going. Quiet road with easy access to Portland and also points further north. Thanks so much for the opportunity to stay at this special lodging!

Such a beautiful and peaceful place!! my kids didn’t want to leave! Lovely cottage feel with a beautiful view to the lake. We had such a great time taking the kayaks and paddleboard out on the water and enjoying our coffee overlooking the water from the sunroom,. Thank you for the great family memories!

This cottage is perfect for Sebago if you own a boat. She has everything you could need for a stay on the water. I would love to stay here again this year.

I’ve been going to Frye Island ME for close to 50 years; as a guest, a renter, then as an owner (for 20 years) and now as a renter again. It is challenging to find “nice” rental properties as many of the rentals are older cottages and the pictures are not representative of their current condition. Austin’s cottage is very new and as such it is just as the pictures show; it is very clean and well cared for! It’s perfect for a family of 6.

The time that I spent at Julie’s camp was amazing! It was even better than described! Julie thought of everything from sharing restaurants and things to do; an awesome multi-device charging station; and even a welcome snack basket and bottle of wine. My pup, Gracie, had a great time as well scouting all the waterfowl on the lake and just having some good country fun. I hope to get back to Julie’s amazing camp at the end of the summer. It’s a real gem as is the host, Julie.

Such a lovely spot! Our dogs and little family really appreciated how clean the home was, and that there was so much privacy/space for our dogs to be outside (off leash)! A nice, cozy stay while we attended a wedding for the weekend.

Kevin's place worked really well for my two dogs and myself. There is a fenced in back yard. I liked the setup of the primary bedroom with the attached full bath and laundry. Comfortable bed! Very quiet neighborhood and very convenient to access other areas of Portland. I really appreciated the back deck setup. I need to find the comfy chair they have out back for my own home! Clean and usable kitchen. Nice stack of Maine materials and recommendations for local items to check out. Overall, a very pleasant stay, thank you!

We had a great week at Ashley’s place! We used the kayaks several times and walked the trails nearby. House was very spacious and comfortable. Highly recommend!

Our stay at Jordan’s beautiful place was wonderful. The house is exactly as pictured. The one addition is that along with the kayaks, there are also two paddle boards and a couple of pool noodles. We enjoyed everything from the spacious rooms to the fire pit outside (for s’mores) to the cozy indoor gar fireplace. We had a few questions and a concern during our stay and Jordan was very responsive and hospitable. He even came by to ensure everything was ok. Lastly, the neighbors are incredibly friendly and the neighborhood/lake is quiet and peaceful. Plus it’s about 45 minutes to Freeport (for great shopping) and Portland (for delicious meals). Whether you’re looking for a quick getaway or a longer stay, Jordan’s place is perfect for both couples and families.

This is a beautiful setting, and the house itself is very modern and comfortable. With great views from each bedroom. The location is nice - 20-25 mts from Portland and its nice restaurants. John is a very responsive host - always available, very flexible. I would recommend the unit as well as John, and would return here.

Had a small bachelorette party here for one of my closest friends. It was the perfect place for a more relaxed girls trip but close enough to get to downtown Portland for any shops, sightseeing, and food! Highly recommended.

My family and I had a serene experience staying here. Although the weather was mostly rainy or cloudy, we loved the lake location and maximized the indoor, outdoor, and nearby activity options. The hosts were so responsive, regardless of the question, and made this a truly delightful visit. This was my parents’ first Airbnb experience and it set the bar higher than I could have imagined! My family and I are already talking about coming back!!

This was the best experience we’ve ever had with Airbnb. From start to finish, Christian’s communication was excellent. I honestly wish everyone were as communicative and proactive as he is. This place truly left a mark on us. Our experience was so amazing that we genuinely want to recommend it to everyone. It was impeccable full of thoughtful details. We reconnected deeply. Everything was just perfect. I didn’t want to leave. The details won me over, and the intentionality behind this place is something truly special. I’m genuinely in love with this place. 💛