House holiday rentals in Pittsfield

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!

The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

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

We had a wonderful stay at this adorable home in the Berkshires! The house was very comfortable and cozy, and the backyard with the deck and pool provided a wonderful space to hang out day and night. The house was situated 20-30 minutes from so many places - downtown Lenox, Miraval Spa and Ballderdash Winery. We can’t wait to come 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.

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.

This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.

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!

My family had an amazing time at Marie’s place. Accommodations were exactly as described. The number one thing I look for in a place is cleanliness and Marie’s place was impeccable. Marie’s place is on a nice neighborhood street in a friendly neighborhood. We felt right at home. Marie goes above and beyond on the details, extra toiletries, snacks, coffee, board games and books for adults and children in every room. She also checked on us after our first night just to make sure everything was going okay and to make sure we didn’t need anything. Marie is an amazing host! Best airbnb we have stayed at. We would definitely recommend.

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.

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.

We had a wonderful time and this house is completely amazing. There is absolutely nothing missing! When Tiffany said, "all you need to bring are clothes" she wasn't joking. The person who designed the house was a genius with the master bedroom on one side of the house, the 2nd bedroom on the other side and the 3rd on the 2nd floor. Privacy inside as well as outside. It was a hiking trip for the family and included Kennedy Park, Olivia Outlook and the Great Monument Mountain. After spending the day hiking, the hot tub, playing pool and watching a movie in the theater just ended a perfect day. We didn't realize how close we were to MA and it was bonus to explore Western Mass as well. Thank you Tiffany for sharing your home with us.

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 went to Chatham for a wedding near by and could not have asked for better accommodations for a weekend out of the city. Hope to go back!

BBs Retreat was a beautiful home in a very walkable neighborhood. It was clean & had everything that we needed for our stay. Thank you!

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!

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!

Karen’s place is amazing. She is so thoughtful in providing all the little things that you wish you had. First aid kit , Kleenex. Paper towels. Plenty of toilet paper! Beds were amazing. Sheets were amazing. The best equipped Airbnb I’ve ever stayed in. She was so helpful with local Recommendations as well! Thanks Karen! We will be back !

Eli's home is in a great location; easily walkable to MassMoca and downtown. It's small but cute and has everything one needs to cook, rest, etc. There are a couple of things to be mindful of... - The upstairs bedrooms get quite hot in the warm weather, and the ACs are very loud, as is the fan. I highly recommend bringing earplugs; we only had one pair, and my husband didn't sleep well during the hot night (we both slept well the other nights!). This is not the first time we've experienced this at an Airbnb, and it would be super nice if hosts provided quiet ACs for their rentals. Eli is responsible, so I'm sure he'll figure out an alternative. The bed was very comfortable! - There are a lot of steep stairs (inside and out), which normally isn't an issue, but we were traveling with our heavy e-bikes and had to carry them up and down the stairs, and that kept us from going for several spontaneous bike rides. Overall, we enjoyed our stay at Eli's and would recommend his home.