House vacation rentals in Pittsfield

My friends and I spent the long weekend here for my bachelorette, we definitely could not have found a better place! Each room has been decorate with such style and care, everyone was blown away that it was even cuter in person. There was plenty of space for everyone to be comfortable, and the two living spaces were perfect for us to hang out and play games. We were also able to put to use the included kayaks as well at the hot tub, which was perfect for the unexpectedly chilly end to our weekend. Vincent’s instructions were super clear and communicated ahead of time, not to mention, it felt like all of our needs were anticipated with included toiletries and kitchen/bar supplies. The stay was seamless start to finished. We definitely hope to stay here 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.

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

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.

This property is beautiful! The house and amenities are actually just as nice in real and every detail was so thought out. Arp really has good taste and communicated well throughout our stay.

The house was beautiful and very family friendly. They greeted us with milk, orange juice and a carton of eggs in the fridge. They even had a selection of beer testers for my husband to try. We had an issue with the pool heater not turning on and both host were very helpful and responsive. I loved the hand drawn map guide they made me when I could not locate something ! They even got someone out there that same evening. Especially on Memorial Day weekend I was impressed on how quickly. I would definitely recommend this home to anybody and will go back if I’m ever in the area again.

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

Everything was what we expected. Very clean and organized. Hot tub was awesome. Great yard. Mattresses could have been more comfy but weren’t terrible. Overall it was a perfect weekend and we would definitely go back! A great choice!!!

My husband and I had a wonderful stay at Sarah's historic home with our two grown children. The house was clean and extremely comfortable with lots of space for all of us. We felt welcome from the moment we stepped through the door. From the personalized welcome sign, to the flowers and wine and so many extras not usually provided... coffee, mints, tissues, throw blankets, an emergency kit, plenty of towels, and a new toothbrush for my husband who forgot his. The weather didn't cooperate for us to use the outdoor spaces, but we can imagine how wonderful it would be to enjoy the porch and the back deck. We highly recommend staying here if you are in the area.

Wonderful place on the lake with a great host. Janice was very responsive, offered an early check-in and set up a baby gate. Great place for dogs and kids.

We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!

The Hygge House was a lovely spot to spend my birthday weekend with my family and friends. We took advantage of so many close-by activities. But the highlights were at the house itself - paddling the canoe and kayak through the water, outdoor dinner, and s’mores at the fire pit. Jessica was also so easy to communicate with and super accommodating during a personal emergency we experienced. We loved our stay and would love to come back again soon.

Our company stayed at Deborah and Ashley’s for 10 days and we had a wonderful stay. We were incredibly comfortable and there was enough room in the house to find separate work space as well. Highly recommended would stay again and D and A were fantastic at communication. 5+!

Great stay here with 5 adults and a teenager. Plenty of room to be together or spread out. It has one of the best equipped kitchens ever! The location is perfect for skiing atJiminey, Bosquet or Catamount. Lots of options to pick from and plenty of good food in the area. Exceptionally clean place and very comfortable beds. Would stay again!

We had a great stay! Vinicius’s home was clean, conveniently located to explore the Berkshires and easily accommodated our party of four, plus a dog. The fenced-in yard came in very handy with the latter!

As soon as I entered I contacted Anne-Marie and said it is exactly what Airbnb should was when it started—a family home that we were able to stay in. It was cozy and homey and everything was very clear and easy to use. Both Anne-Marie and Patrick were friendly and professional. The location is great as it straddles North and South Berkshires. One night we are in Williamstown and another in Lenox. Both were right along route state route 7. You are also right next to fantastic skiing at Jiminy Peak or Mount Bousquet.

We only stayed one evening but found the living space to be perfectly laid out and spotless. The kitchen is fully stocked with about every utensil and appliance you can think of. We especially enjoyed the fresh eggs, treats, and flowers that welcomed us! The living room was especially comfortable. The unit is attached to the rear of the main house but it’s kept totally private. There aren’t many places to eat in Richmond — after all, it is pretty rural— but Stockbridge and Lennox offer many dining options.

Paul's house was everything I needed for a quiet weekend with the kids. The house is cozy, easy to keep organized, and well lit. The view of the lake is the cherry on the cake. The backyard is huge, so my kids had plenty of time to play outside. The neighbors are very nice and quiet. I've never slept in a house as quiet as this one. Paul is very kind and helpful. I will definitely be back.

We were happy with this AirBNB and would stay here again. It was nice and quiet but a very short drive into Great Barrington. Close to lots of hiking. Updates have been made since some of the previous reviews. There are two couches in the living room and some of the stock items in the kitchen for convenience.

Easy to find, beautiful location, clean, comfortable and most importantly peaceful and quiet!! I think we will return for sure!

We spent a wonderful weekend celebrating my daughter's graduation with our family. The house is beautiful, and Lauren and Blake are extraordinary hosts. I totally recommend this house.

Jaryn is a terrific host -- responsive and helpful in every way. The property is ideally located to access the northern and southern towns in the Berkshires. There are trails at the top of the cul de sac as well as Shaker Mountain just up the road. New Lebanon has some hidden gems for eating such at M & M's, Blueberry Hill Market and Marios. Easy to get to shopping in Pittsfield and Lenox. Great place to relax and hang out as well as taking advantage of music, art and cultural activities in Lenox, Stockbridge and Becket. Most of all, there are the most amazing sunsets every night!