Vacation rentals with a patio in Pittsfield

We loved staying at Janet’s place. And would stay here again. The studio is beautiful, comfortable and spacious and had everything we needed. We loved the clawfoot tub and shower. It is truly is a special place to stay. It was a quick walk to Warren Street and to Amtrak trains. Thank you for being a great host.

We enjoy old houses, so we found Emily's house a gem. It is a beautifully renovated space that includes modern conveniences but leaves the beautiful old doors and floors to give depth and beauty to the space.

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!

The place is amazing! It has a nice backyard. Real charming place!

We had a wonderful stay at Katherine’s beautiful cottage in Kingston. The home was cozy, clean and thoughtfully decorated ~ truly a perfect retreat. Surrounded by nature, the peaceful setting made it easy to relax and unwind. Katherine was a warm and responsive host, making everything seamless from start to finish. Highly recommended for anyone looking to enjoy the charm of the Hudson Valley!

Really clean and perfect for what we needed it for! We were there to move out our daughter from Williams College and it worked out perfectly.

The super host Bruno was “super”! He was a pleasant timely communicator. My partner and I stayed for one night. We were very pleased with the space. It was clean and spacious. The queen bed was very comfortable. The living room had cozy furniture. The shower had amazing water pressure and plenty of hot water. I suggest you read the instructions of how to turn the shower on and set the temperature in the listing. The location was perfect. It was only an 8 minute drive to Northampton center which offers a wealth of restaurants and unique shops. Also it was only a 2 minute drive or 20 minute walk to Florence center. Definitely check out the Florence Pie Bar, Miss Florence Diner and Coopers Market. Just a 10 minute walk from the apartment is Masa Mexicana- a great Mexican restaurant. The apartment was in a very quiet neighborhood and set in back, on the second floor. It was private and looked out onto some pretty greenery. It had all the amenities. We would definitely stay here again!

We had a good time. This was a great place with beautiful views!

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!!!

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.

We had a slight delay to our trip due to health issues but Lisena and James were very understanding, flexible and caring. Very flexible with our check in and out during our stay since we unfortunately had to shorten it. We are looking forward to planning another night soon. Thank you for sharing your beautiful home with us. We visited the general store right down the road, definite must see, very cute friendly family owned store and was impressed with finding all local milk and products and also gluten free options for baking etc. we also went to Stockbridge to explore the town and to hilltop orchard.

Bucolic, 18th century home with a world class host. We would unquestionably recommend this place to anyone.

Leslie's house was wonderful. Comfortable home with lots of space in a peaceful setting. Beautiful views and walking distance to a bird sanctuary with nice trails. We would love to stay here again.

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

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!

Anait has a beautiful house which was great to accommodate two families. We used her house as our home base while skiing and touring the beautiful Berkshires. We got about 8 inches of snow and she was responsive in getting the snow plower to come. He even come back again, so we could take the cars out of the driveway and plow it! She was responsive and gave great instructions. The house was warm through the super cold winter days. We loved cooking in the well equipped kitchen and the bathrooms are in great shape. Just felt like an extension of our home. Great restaurants in the area! Thank you Anait and we look forward to booking again here.

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

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.

This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.

Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

Ashley has a great place!! It was a fantastic place to visit with my friends and reminisce. Weirdly, this rental turns out to be the place my great grandparents lived and did business as my grandma grew up. I did not have any ghostly contact with my relatives in the apartment (I was kind of hoping and not hoping to see them 😂), but I still had such a meaningful time sitting in the spaces they did so many years ago. Ashley is an excellent host and I will come here again next time I “come home”. 😊

Excellent location and central to all things fun in southern Vermont. Loved the sports center amenities. Very peaceful considering it was end of mud season and not busy at all. We used the pool, workout facilities and locker room. Even had a fireplace we could use ! Christine was incredibly responsive and welcoming. Would recommend to others and would stay again if in the area.

Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!

We had a great late season long ski weekend at Elizabeth’s condo at Mount Snow and would definitely recommend this place to others. It was clean and cozy and we had good communication with the host. The condo wasn’t the most renovated but it was clean and comfortable, had all of the desired amenities (dishwasher, washer/dryer, fireplace, good heating system, large comfy couch, and two full bedrooms and bathrooms with a third loft room) and had more than enough space for our group of four. We were able to easily walk in about 5 min to the Sundance parking lot and lift (only open during the weekend during our trip). Elizabeth sent some good restaurant recommendations as well. We hope to come back soon! Thank you for a great trip!