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Cottages in Windsor

"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "

"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"

"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"

"The cottage was clean and as described. The street was very quiet."

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."

"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...

"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "

$1,784 nightly

Sep 9 - Sep 10

Total includes taxes and fees

"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "

"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "