Holiday Homes in Chester

"Great place and views. "

"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "

"My grown daughter and I stayed here for a two night visit to the Berkshires. It was so nice to have an entire house rather than a hotel room! We received our check in email in plenty of time, the house was clean and furnished with generous amenities such as soaps, shampoos, coffee, etc., the owner was readily available. The house is close to the road, but it really wasn’t a problem…white noise machines and air purifiers made sleeping very comfortable, and there was very little traffic noise....

"Perfectly located and lovely appointments make this the place to stay when visiting Lenox, Tanglewood, etc. The home is farm in style but elegantly decorated with thoughtful combinations of old and new. Well laid out floor plan allows groups to host friends and families at the same time. You will be delighted by mornings in the kitchen or evenings in the living spaces. Enjoy! "

"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"

"At the end of a dead-end street but only two blocks from the center of Stockbridge, this century-old charmer may be the best-kept and best-supplied rental in the Berkshires. We stayed a month(!) and loved it. The location is unbeatable, an easy walk from the Red Lion and within 15 minutes of Tanglewood, The Mount, the Rockwell museum and other attractions. Four local trails begin 100 feet away, including the Ice Glen. A beautiful, productive garden awaits, and the screened front porch may be...

"Clean, updated home in the perfect location. Loved the screens in porch! Holly is a wonderful host and her home is a perfect getaway."

"This was the perfect place for enjoying our visit with our adult children! Very well appointed home and we had a very lovely visit! Peaceful and lovely location!"

"Loved it!"

"My partner and I were in MA to drop our eldest at Smith College for their first year. We chose Flight's End for the location and the fact that we were allowed to bring our pups with us. It was incredibly peaceful and just what we needed during an otherwise emotional time with such a big transition for our family. "

"Very quiet central location in the Berkshires. Close to all amenities. Enjoyed the lake canoeing and site seeing. Great house with everything needed. "