Holiday rentals with outdoor seating in Windham

This cozy and beautiful home was squeaky clean and very well organized. Our kid enjoyed going up and down the staircase. We only stayed overnight but would have loved to extend our stay if possible. Would definitely recommend!

We loved this place! We were renting for our daughter’s college graduation, and even though it poured all weekend- we really enjoyed just hanging out at the house. Mostly I loved loved the king size bed and I’m going to ask where the owner got it - slept like a baby!

Amazing place, host was super kind and accommodated my family’s last minute booking since we were cancelled on twice that week! We are super happy we found this adorable beautiful place that ended up being better than the other places would have been anyway!

We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.

This house was perfect for me and my guests! All 7 of us fit perfectly, It didn’t feel too overcrowded! We loved the beautiful view off the deck and the hot tub was an amazing touch! The house was very clean and had everything we could’ve needed. I loved how clear the instructions were for everything and how responsive the hosts are if you need anything!

We loved our time staying here, the house was beautiful and just as described/ seen in the pictures. Randy was a great host and always very responsive with some great local recommendations. Would definitely love to return!

It has been a wonderful experience getting to meet and work with this couple! Very understanding and accommodating and beautiful home and location I highly recommend!

Great location close to downtown Portland. Lots of walkable places close by for coffee and breakfast. A little farther to some unique restaurants. We Uber'd a lot which worked out great to avoid parking around Portland. We would definitely secure this nice place the next time we come to Portland!

My boyfriend and I had a lovely stay. We enjoyed drinking coffee out on the patio in the mornings and cooking meals in the kitchen. The place was clean and just what we needed for the week. Victoria and Tanner were also very friendly and quick to reply to our messages. We would come back!

Great little place. We parked our car and trailer right in front of the house, had takeout and a few groceries delivered (I think we used DoorDash or GrubHub), and got rested up for the next leg of our trip. Hyeri was super kind and responsive.

Arian’s house is so lovely. It’s cozy, modern and very clean. The house is in an excellent location close to restaurants and walking paths. Arian was responsive and helpful. We highly recommend his place if you’re looking for somewhere to stay in Portland

My dog and I had a great time here and would recommend to anyone looking to stay in the area. We found lots of dog-friendly hikes and nature reserves nearby within 15-30 minutes . Otherwise we enjoyed the peaceful yard and small brook on the property. Beautiful and thoughtful rental, with very friendly hosts.

The apartment was very comfortable. We would definitely stay there again if we’re ever back in Portland.

A lovely place to stay in Portland’s East End. Great location in a very quiet and walkable neighborhood. (I happily did not need a car during my visit.) The apartment is great, with a comfy bed, smart TV and a nice little patio too. And you’re just steps from the Eastern Promenade park, which is one of Portland’s best amenities imo and leads to a beach, waterfront trail, dock w/ kayak rentals, etc. Jennifer was a very kind host; thank you!

Carlo is a very cool person and the space reflects that. Its very cozy and in an amazing location. The smoke friendly back yard and games available leave a lot of good late quiet hangs and safe feelings with that. I cant recommend this spot enough if you have good legs to make a journey or a car to make it easy. I felt right at home and never too intrusive on my part or on the hosts. Even if you dont want to move much it couldn't be a better location. I will be back there.

Great stay

Very nice stay! The location is perfect, everything you need is on site. I recommend it!

We had a great time! The place was very clean, nicely maintained, and in a perfect location—just a short drive to local coffee shops and great restaurants. The surrounding nature was absolutely beautiful and made the whole trip feel relaxing and refreshing. Highly recommend!

Wonderful little spot very close to the beach. Plenty of places to walk to from the location as well as a short drive to Old Orchard Beach. Would come back in a heartbeat!

We had a great stay at Tysons place. Its a perfect location, only like 5-10 minutes drive from Old Port. The home is clean and beautiful. Street parking was super easy. Always space right on the side of the home. Each room has its own A/C. Would definitely recommend staying at Tysons place!

This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.

Great place! Close to the beach. Easy and fast communication when we needed to specify parking questions.

We loved our stay! The space is beautiful and cozy. The walk to the family friendly beach was just the right distance for my 4yo. The neighborhood is adorable and friendly! With an amazing bakery and ice cream shop just around the corner! Dave was a great host and took great care of us.