Search Vacation Homes in Winchester

"Great place, friendly check-in"

"Very clean home and easy onsite parking. Good location as well!"

"The property was exactly as advertised. Spacious bedrooms, a well-stocked kitchen, and plenty of space for 8 people. There is a Target only 3 minutes away, and loads of small restaurants within walking distance. My family and I were very pleased with the house. Thank you for the positive experience!"

"Everything was wonderful . The only suggestion would be to have a couple larger pans for cooking "

"very pleased with our stay! "

"We enjoyed our stay! Great location, easy parking. Wonderful communication from host. Would stay again!"

"Awesome, clean, lots of room, great amenities."

"This house was exactly as described and perfect for our family trip."

"Beautiful and clean. Very friendly and helpful host. If ever in the area would definitely choose this lovely home first!"

"Great location. Host was communicative and easy to connect with. "

"Everything was great for our 2-night stay with 3 adults/3 kids!"

"The home was in a great neighborhood. The home is also super clean and hosts were responsive and helpful. "

"Very sweet place to stay. Located in a very nice area. Close to the "T" and very walkable "

"great location with everything about 15 to 20 minutes away."

"We stayed here for my brother’s MIT graduation, and I cannot say enough good things about this stunning property. Finding a home that comfortably fits the whole family can be a challenge, but this place was absolutely perfect. The house is gorgeous, incredibly spacious, and felt like a true home away from home. Being so close to Cambridge made our commute to the commencement events stress-free. If you’re looking for a beautiful, high-end spot for a family gathering, look no further. Five stars...

"We were very excited to stay at this property with my mother and her 2 dogs. My husband is allergic, so the dual homes side by side seemed perfect - and with 2 medium-large dogs, 2 fenced backyard areas was perfect in the Boston area. Unfortunately, though the owner was aware we were bringing dogs, he failed to mention that "fenced" actually meant fenced just in 3 sides, not fully fenced. Moreover, the 2nd "yard" measures about 4x4 ft or so - also not fully enclosed. The photos were...