House vacation rentals in Windham

Very nice place easy access to routes 4 and 100 with plenty of things to do

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

Great stay and was exactly what we needed for our entire family for a weekend wedding!

Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

This house was the best ski weekend away! Conveniently located yet secluded for a peaceful stay. The home itself is spacious, charmingly rustic, and thoughtfully stocked with everything we needed—especially the fully equipped kitchen, which made cooking a breeze. The atmosphere was cozy and inviting, making it the ideal spot to relax and unwind. Highly recommend.

Ariana’s place was great after a day of snowboarding at Stratton. Great location, the home was cozy and we had a great time relaxing at the house. Ariana was responsive to our question and the home was well equipped to enjoy a meal at home after being out all day.

Beautiful, spacious house, just as described. Clear instructions and responsive hosts.

Kelly was very responsive and helpful. She went out of her way to get us a last minute booking and it didn’t disappoint! It was clean, well stocked and very comfortable! I will definitely book this again when its available!!!

Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Bermet and Danny’s home was the perfect spot to host my husband’s surprise 40th birthday ski weekend with friends. Along the way, they were very responsive to our messages, flexible with our needs (early check-in, etc.) and friendly to deal with. The house was really unique and super convenient to several mountains. This was a 5-star stay and I would visit again for sure! Thanks to the hosts for their hospitality.

This was our second stay at the farmhouse. We love this place! Wes and Lindsey are so nice and welcoming. The house is roomy, clean, and the property is beautiful. We most enjoyed walking our dog on the path out back, and spending time with family we have in the area. Hope to stay many more times!

My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again

Really nice peaceful place to stay. Was super clean and a most interesting house with many antiques, brought back many memories from childhood. Host was very responsive and very friendly. Would definitely stay there again!

Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!

First and foremost, Julia is one of the most accommodating and most responsive hosts I’ve ever had. She was very friendly and proactively looked for ways to help me and my group feel welcome. Beautiful space scenically located on a Vermont mountainside - would absolutely recommend!

Truly a historic home and a very nice place to stay in the area. Exceptionally well supplied for preparing meals! A big plus for us as we don’t like to eat every meal out. Communicative hosts and pleasant environment, I recommend this location to folks visiting the area!

We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!

Great stay! The Chalet is nice and secluded. A Great way to getaway with friends and/or family. The size of the stay is great for those looking to spend time intimately. Everything you see is what you get. There were no complaints with our stay and that is why it deserves a 5 ⭐️. The hosts are kind enough to have had firewood available for use of the fire pit. The hosts were both hospitable and responsive. I hope to stay there again maybe in the winter to go skiing or snowboarding. The towns of Ludlow and Springfield are roughly 15 minutes away in their respective directions with tons of dining options and activities. New England Cider donuts is right on Main St. in Ludlow which is a great spot for breakfast sandwiches and pastries. Okemo Mountain is a great hiking experience also found in Ludlow. If you find yourself looking for a quiet and peaceful getaway, don’t give it a second thought and just book this place you won’t regret it!

We were 2 couples and had the perfect stay! Really cozy house with a great porch and hot tub! We loved playing ping pong as well! Would 100% stay there again!!

We have had a marvelous time at Gideon Lee in Chester, Vermont. An extremely spacious house, equipped with all the necessities. A well-functioning kitchen, a washer and dryer and especially a cozy "wood stove". Polly and Ian are friendly and interested people with whom you are happy to strike up a conversation. And who are happy to give all kind of suggestions for trails, restaurants, or just for visiting nice villages. In the five days we were there, this house became a home!