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Compare Cottages in Windsor with updated reviews, rates, and availability.

Richmond Vacation Rental | 3BR | 2BA | Steps to Enter | 1,210 Sq Ft

"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."

This living room has an oversized sectional with a large fireplace and smart TV.

"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"

"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."

"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"

Richmond Vacation Rental | 2BR | 2BA | 1,750 Sq Ft | Stairs Required

"Comfortable. Homey. Very well stocked, especially the kitchen. Plenty of room and light. Thank you for our visit. "

Pittsfield Vacation Rental | 4BR | 1.5BA | 2,000 Sq Ft | Step-Free Entry (Ramp)

"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."

Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required

"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "

"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...