House holiday rentals in Pittsfield

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

We had a great time at Natalia house, a very big house with a lot to do for my three years old daughter. Will definitely stay here again.

What a great spacious home. Plenty of room for the whole family. Clean and neat! Beds were super comfortable! Great water pressure. Beautiful back yard and three season porch. This was our second visit here and it was just as great as the first!!

Beautiful house in upstate with a hot tub and barbecue that allowed us moments that we won’t forget. Chris was very responsive and maintained the communication throughout our stay. The house was spacious, clean, great amenities and extra care from the host. The location was also good, close to Hudson but private. We loved it and hope to be back soon!

An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

Great place. As described. Met our expectations.

The house is amazing, and the host was responsive! The location is beautiful and quiet, perfect spot for a getaway. The only advice I would give is to arrange transportation ahead of time. We relied on Uber/Lfyt, and while we ended up being able to make it work, drivers often weren’t willing to drive all the way out there and we were nearly stranded and had to adjust our plans to make sure we had a ride. But if you have a car or rental, this is the perfect spot! Only 20 minute drive from downtown Kingston, but feels very remote and cozy.

Perfect for our Easter family gathering! We especially enjoyed spending time in their delightful backyard cooking on their gas grill and admiring their exquisite flowering trees!

This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

Could not have found a better place for our trip to Hudson! The spot was gorgeous, spacious, well-located, etc.

A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

We loved staying at Jeffrey and Juan’s quiet home on the rushing Chittenden Creek! Jeff is a communicative, friendly, and accommodating host and would absolutely recommend his place to others. I surprised myself at how much I loved the bird watching (don’t worry, Jeff has binoculars and a book to guide you!). Don’t miss out on the Empire trail for early evening walks! My husband and I stayed at their home for two weeks as we both work remotely and there was plenty of space to spread out and take calls. The plant room in their home is so beautiful that people complimented my ‘digital’ background on zoom! Would absolutely stay again.

This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!

Our group of 3 felt right at home! Nice decorator touches - Dash and Albert linens and rugs & lovely soaps added a luxurious feel. We were too busy exploring Hudson to miss the TV, but if that’s important to you, take note. Hosts were super responsive. We can’t wait to return!

The home was very clean and as described with everything we needed for our visit. Chris was very clear with his check-in instructions and quickly responsive to questions as we got settled. I would stay here again.

This is a good example of what you should expect from a well run and thoughtfully put together Airbnb. everything was well done. little touches in the house make a difference and just feels better. I can see how a second privacy screen in the hot tub area could give a bit more privacy, but not a big deal. great spot. highly recommended.

This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

This is our second time staying here when we come to visit family. We love the location, quiet and just a couple minutes from our grandchildren. Easy access, cute cozy clean home nice kitchen amenities.

This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.

Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!

Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

We had an absolutely wonderful stay at this Airbnb! From the moment we arrived, the host was incredibly welcoming and made sure we had everything we needed for a comfortable stay. The space was clean, cozy, and beautifully decorated, with thoughtful touches throughout. The location was perfect—quiet yet conveniently located. I would highly recommend this place for anyone looking for a relaxing and enjoyable getaway!

If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.

The 5 of us, plus a little dog thoroughly enjoyed our 4-night stay at this super spacious, clean, and well-stocked house. The house is within walking distance to the shops and restaurants in town. We’d definitely recommend this place to anyone looking for a convenient and comfortable stay in the area!