Vacation rentals with outdoor seating in Pittsfield

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.

Vincent's lakefront Catskills home exceeded all our expectations! The house is perfectly designed for group gatherings, with multiple comfortable living spaces that allowed our friends to either come together or find quiet moments. We had private chefs come for a couple of dinners and they had everything they needed to create memorable meals. The lake views are absolutely stunning. What truly set this experience apart was Vincent's exceptional hospitality - he was incredibly responsive and accommodating when we experienced travel issues, going above and beyond what was required. This thoughtfully designed lake house with its beautiful surroundings and attentive host made for the perfect meeting spot for our friend group. We'd gladly return!

We were tremendously happy with our weekend stay. It was a beautiful space that had us feeling serene and relaxed from the moment we stepped inside. Highly recommend! Thank you!

Well kept clean old house and furnishings. Terrific unobstructed view of the Hudson from two of the bedrooms and living room facing East. I loved sitting by the bay window in the master bedroom with the sun shining in watching barges on the river and with views of the town of Hudson on the far side of the river. The owners stuff was in the closets and refrigerator and freezer full of her food but that did not bother me. I appreciate having condiments, salt, sugar and pepper available. There is a washer/dryer but no dishwasher and only one bathroom. Also no shades on the East facing window in the master bedroom so light streamed in at sunrise.

Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

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!

Cool and nice place. Clean house and welcoming host. One thing you may consider is it's right next to railway - around 20 trains pass by each day and some of them go through midnight. But if you are a train lover like me, this is a sensational place.

Great spot! Stayed at Eric's place for a weekend with a group of college students (8) looking to hit the reset button and had plenty of space. It was spotless and comfortable, and we had no trouble finding what we needed. The virtual guide is also super helpful!

My wife and I needed a place to stay due to a family emergency, and Donna was extremely responsive when we contacted her with questions about the home. I was very impressed with her communication throughout our stay. The house was perfect for what we needed and we felt at home as soon as we walked in. The location was perfect. The house is on a quiet street, there are sweet little chickens in the back yard, and the dog run for our 2 pups was fantastic. We were very lucky to find this dog friendly place. Donna even offered to walk or feed our dogs for us if we couldn't get back from the hospital/my relative's home in time. The beds are comfortable, but they are a little small. I believe one of the rooms has a twin and the other two rooms have full size (maybe double?) but it worked for our two nights. Donna left us a few farm fresh eggs, fresh flowers, and fresh baked cookies and we felt very comforted by all of that. Donna is an EXCELLENT host.

We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

Susan’s place was quiet, clean and lovely. Close to town, but still in a wooded area. The apartment is well designed with everything you could need, including delicious coffee.

Thanks Crystal It was a great spot for the weekend and very comfortable!

It was a great experience, very easy to get to.Super clean we enjoyed our stay!!

Second time staying at Susan's. Easy to get around Troy and the Capitol Area. Clean. Quiet for the most part. Was easy to book last minute. Cute outdoor space.

Susan’s place was lovely! We had a very nice stay for my sister’s wedding. The bathroom is so big and beautiful! Thank you :)

Great stay at Marlene's place! Good location, nice apartment. Everything as described. Responsive host. Would recommend!

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

I enjoyed my stay at Caitlyn and Joey's place. It was just a short walk from both the Equipe sports store and the Mount Snow Sundance lift, the latter being a great starting point for days on the mountain. Next to the lift is a waffle cabin, which made for a tasty post-mountain snack. The apartment was clean, the fireplace toasty, and the hosts responsive. I'd definitely recommend staying here, and am looking forward to staying here again myself!

Superhost ! Was so accommodating to get us in last minute since our other Airbnb didn’t work out. He was so responsive and helpful with the snow storm as well ! We were so glad to have found this gem and have such a gracious host. The location is perfect and walkable to all the restaurants and markets. Also 15 mins away from Berkshire East ! This was a great find and we are thankful for it !

Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.

Second stay at William’s. Loved it again the second time, great area and super close to Mt Snow resort. Great restaurants and of course the Snow Republic Brewery nearby. Thanks for the great stay!

What a wonderful experience at Goran’s 2nd floor condo! Gorgeously appointed space. Beautiful views from the porch. A mile from bustling Northhampton and a great value, too. Goran was also very friendly, prompt, and responsive in his communication making the stay seamless.

We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

We had a great time staying at Kens place! Ken was very responsive and accommodating! Thank you!