Vacation rentals with a pool in Pittsfield

We had a good stay at Victoria’s farmhouse. The location is really peaceful and relaxing, surrounded by nature—perfect if you’re looking to unplug a bit. The house itself is beautiful and very comfortable, with unique interiors that feel like something out of a design magazine. Victoria was easy to communicate with and helpful when we had questions. It’s a bit off the beaten path, which we liked, but still just a 15-minute drive to shops and about 30 minutes to the train and some great restaurants in Hudson. Overall, a lovely spot for a quiet getaway.

We had such a fantastic stay at the field house. Jane and Steve were excellent hosts and extremely responsive. The house is beautiful and we were lucky with the weather so we could take advantage of the immaculate garden and the outdoor dining area, not to mention the pool, hot tub and fire pit! Highly recommend.

This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!

We loved staying in this beautiful home. We were here for a college reunion, so well situated in the Berkshires. The home was quiet and private, the pool was amazing, and the space was incredible. Most of all, the thoughtful amenities - children’s toys, movie theater, swim toys - were very appreciated. The owners were very receptive and responded right away to questions, and all in all it was a most wonderful place to be!! Thank you!!

We stayed here for about a week to getaway away from the city and we absolutely loved it! It was the perfect place to recharge and relax. Everything was as described!

We had a wonderful stay at this beautiful property! The location is close to plenty to do and great dining but also feels very private. The home is absolutely beautiful as pictured. The pool was a real treat to have and half of the pool is a shallow end which was a bonus for us traveling with a child. The beds are very comfortable which is always a huge plus when traveling. The hosts were responsive with any questions that came up. We would happily stay again!

Thank you for a clean and comfortable stay! We were in town visiting family and this was an ideal central location. The pool was a fun addition for our kids plus we were able to turn on the heater ourselves with no issues. Property was exactly as described and it had almost every kitchen gadget for the home cook. There was even a well organized drawer of glass storage containers. Convenient and thoughtful! It’s always quiet and peaceful whenever we visit the Berkshires and this trip was no different.

Great location, thoughtfully stocked and beautiful home. Perfect for my long distance girls weekend!

Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.

We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

Great little studio spot to use as your Basecamp for activities in the area!

Great stay at Renee’s! Right off the lifts. Easy storage for skis and ski on ski off. Clean room with all the necessary amenities. Restaurant in the building if you don’t want to venture far. Cozy fireplace in the lobby with coffee and hot chocolate bar. Overall a great long weekend at Jiminy. Thnx!