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!

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.

Beautiful, historic home in a lovely neighborhood close to downtown Keene. Charming and cozy inside and out. Comfortable beds and furniture. Wonderful artwork by Ruth throughout her home. Large bright kitchen with everything you’d need to stay. Enjoyed the architecture and restaurants in Keene. Highly recommend Ruth’s home to stay in this area!

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!! 🤩

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

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.

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!

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!

The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

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

It's possible I've never given 5 stars and checked every chip for an airbnb. This space was absolutely stunning. Such beautiful and peaceful surrounding, loads of clean and comfortable towels, the most comfortable beds (if you like firm beds), the sauna was amazing and smelled so good too, the host was responsive, flexible, friendly, and accommodating, and the interior design and comfort of the home because of its lighting, games, kitchen, living space... just everything, absolutely pristine.

An excellent option for skiing at Stratton. About 3 miles from the base lodge. The unit was clean and spacious. Kelly was proactive and responsive and offered good local recommendations.

Lindsay and Wes' place is a beautifully modernized traditional farmhouse. It is spacious, with comfortable living areas and one of the best stocked kitchens I've seen. The bed was comfortable and the towels are LARGE and fluffy. Out every window are peaceful farmland views. Lindsay and Wes were perfect hosts, giving us privacy but letting me know that they were there to help with anything. Loved our stay and would love to come back if we are in the area again.

Ab’s home is absolutely beautiful and charming. My family and I stayed there for a long weekend and had no trouble finding it or getting in. The kitchen and bathrooms are all updated, and the whole place feels homey and peaceful. We used the grill one evening and realized the propane tank was empty, so I messaged Ab and he pointed us to a hardware store we could bring it to have it exchanged for a new one. He apologized for the inconvenience and reimbursed us for the cost of exchanging the tank, plus a generous bonus for our troubles. This was not Ab’s fault by any means – he said he had just replaced the tank two guests before us so it shouldn’t have been empty, but we didn’t mind the quick trip to have it replaced and truly appreciated his thoughtfulness and communication throughout the process. I’d recommend Ab’s place to anyone looking to stay in the Windsor area!

Great property for my family with lots to explore. The house is laid out very well and the beds are very comfortable!

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!

The house is perfect for a ski getaway. Clean and spacious with tons of wood for the fire and a well stocked kitchen. The hot tub was a perfect t way to unwind after a day out on the slopes.

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!

Great place, especially for the budget. It was clean, comfortable, and had everything we needed for a relaxing stay.

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!!