Holiday rentals with outdoor seating in Windham

Great place! We had a weekend of hiking planned, but with all the rain, we were glad to have use of all the inside amenities here! Sauna, bbq hut, she-shed, basement game room and comfy living room all left us fully entertained while it poured outside. Would love to come back someday!

Absolutely amazing place and experience. Everything about the place was great and the communication and service was the best. We received 5 inches of snow on our last night and they even had the driveway all plowed for us first thing in the morning. That was a very pleasant surprise. Highly recommend!!

It was a perfect getaway for my family - everyone enjoyed themselves, it was child friendly and very relaxing after a big ski day. It is 3 min from Windham Mountain Club, great restaurants and Markets, and we loved sitting out by the brook and having coffee on the deck. We hope to go back next year!

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

Overall a great stay! The home was beautiful and exactly what we needed. Elizabeth was also a great host. We’d be more than glad to visit again in the future!

Taylor has gone above and beyond to create a really special place. My boyfriend and I had a really lovely weekend away with our pups and everything was perfect. We were able to cozy up after long days of hiking, cooking in was just as fun as eating out and we felt right at home. Checking in and out couldn’t be easier and Taylor is very gracious about making sure you enjoy your stay. Would definitely book again!

Amazing place and surroundings! Were looking for a peaceful weekend away and it was just perfect - Kitchen had everything we needed for home cooking and a closet full of board games for some great family time - The view is breathtaking and a great firepit and small creek just below.

The view is everything!! A great weekend getaway

We stayed 2 nights at Bob and Jackie's place with our 2 kids. The apartment was clean and prepared for our arrival which we really appreciate (an extra bed was already made for our kids to sleep). There was enough space for the 4 of us, the kitchen is fully equipped too. Although it was raining heavily during our stay, we could enjoy our time outside because of a little covered area on the back of the building with a view to the woods and a grill that we enjoyed using as well. Thanks Bob and Jackie for a nice and peaceful stay!

We loved how quiet and peaceful the location was. We also loved the homey touches- the local books, the honor store out back, the fact that there was the cafe under the apartment. The setting was beautiful and we loved falling asleep to the sound of the brook and the spring peepers!

Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

Jenna’s place is very comfortable and spacious. We love the town and everything is right there, with lots to do within a short walk. Definitely recommend!

Donna's place was immaculate easy to find shes very responsive. For us personally we needed to make adjustments but she is more than willing to work with us. Appreciate the offer to stay. Highly recommend.

Theresa was an amazing host, she clearly communicated with us along the way, and made sure we had our privacy & provided the upmost comfort. Her space was well kept and full of considerate touches to facilitate a relaxing stay, the subtleties go a long way. We enjoyed the hot tub in the snow, shared a few stories of skiing adventures & loved the friendly visits from Ben. The views were picturesque to boot, we definitely plan to come stay in other seasons.

Great spot to get out of the city for a few days. Perfect location for us as it was very close to friends we were visiting in the area. Walkable to a local coffee shop, cafe, deli/market, wine store, and gas station. The apt was very clean, bright, and had a wonderful historic charm to it. Very quiet, even for being on the main street. Highly recommend staying here for a central location to lots of lovely small towns, hiking, skiing, swimming, fishing, beautiful drives, and good local food. Jen and Caroline gave us great instructions and there was plenty of info in the apt when we got there on how to use the locks, lights, and whatnot.

Very convenient location close by to everything we needed! We did have an issue with something in our unit, but Aaron communicated very quickly and was able to let us use the other available unit for the night. Both Air bnbs at the property were very well stocked and spotless. Felt very much at home here!

This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Daria and Justin were lovely, responsive hosts. It’s a great little apartment — super clean, well equipped with all the basic necessities, tasteful, well thought out decor, a really pleasant place to be, right on the mountain. Small, but perfect for a couple or small family ski weekend. I would definitely recommend and would love to go back.

An excellent place to stay for a ski trip. Perfect location right at the base. Wonderful building with a great pool and hot tub. Excellent for a great ski vacation!

This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!

5 stars, 5 stars, 5 stars!! I would just like to say I’ve stayed in many Air B&Bs before, and this one is by far one of my favorites. The hosts are absolutely amazing. They are proactive in responding and really want you be be comfortable and making sure you have no issues. The price was 100% worth it. I love that they included board games as a part of the space, such a nice touch. The bathrooms and bedrooms were also so clean, and we enjoyed our stay. You can really tell the hosts put a lot of love and care into this place. I can’t say enough good things about them!

Loved the house! I don’t drive, but there are local cabbies in the area. You will see a bear or two as expected so try to take garbage out during the day, not in the evening or at night. The neighbors were pleasant, and I felt very safe. Loved how quiet the community is and really appreciated having a washer and dryer. Bed is super comfy. My only note is that the couch has some spots on it that give me the ick, but I used the extra sheets to cover it up and was fine. Plenty of linens, blankets etc. I love the area so much. I stayed a month for a writing retreat.

Robert's place was a delight! Spotless with many thoughtful touches. We went for a spring snowboard trip to Hunter and didn't try to walk to the lifts (due to the conditions), but the drive was only a few minutes and super convenient. Robert was very responsive and friendly, and made sure we had everything we needed. The property is great with a lovely deck and well equipped. Highly recommend this property; we hope to be back!

We had an amazing stay! The home was exactly as pictured. The location was perfect—just a 30 min drive to Kaaterskill Falls and 5 mins to the local restaurants, but tucked away enough to enjoy peace and quiet. Michael was responsive and made check-in a breeze. We especially loved the beautiful views from the hot tub and how comfortable the space felt after a day of hiking and exploring. The sauna was a great surprise! Highly recommend this place for anyone looking for a peaceful escape to the Catskills. We’d absolutely stay again!