Holiday houses in Winchester

My family of six was extremely pleased with our stay at Dean’s property. He was incredibly responsive and helpful when I was having trouble making the reservation. The home was exactly as described. Very clean. Plenty of linens and towels. My kids loved the game room. Would definitely stay here again.

Doug's place was absolutely stunning and cozy. It was exactly as depicted in the photos. This wasn't exactly an issue but perhaps worth noting that parking can be a little tight due to the cluster of homes. However, we didn't have any problems with navigating the streets. All in all, it was very peaceful and the design of the home was very inspired. Doug was also a fantastic host and very communicative, providing recommendations and very clear instructions. I've bookmarked his place for a future visit.

The place was perfect just like the listing description. Host was quick with responses when needed anything.

Staying in this guest house was really great for me, my wife and our two small dogs. The front of the home overlooks are beautiful marsh. The area is very peaceful, and it's next-door to a quaint little park, and a few minutes walk to a private beach.

Sean was great, very responsive and flexible. the place is perfect for a getaway. Steps from the beach and about a 10 minute drive to downtown Newburyport for restaurants. We enjoyed our stay.

We absolutely loved our stay at Ryan’s place! The home was beautiful, spacious, and pristine—just like the photos. Ryan was a wonderful host from booking to check-out, making everything easy and welcoming. We especially loved the location, with the beach and great local restaurants just a short walk away. We would definitely stay here again!

We had a delightful stay at Matt's and Jenn's. Their cottage is warm and cozy (loved the oversized fireplace), with spectacular views. And while there are many homes nearby, it has a real sense of privacy. The kitchen has almost everything you need (although some good wine glasses would be nice) and the appliances are high quality. We found the beds, with their medium-firm mattresses, very comfortable and we slept well. The wi-fi was excellent and the TV and thermostat didn't require a PhD to operate. Very simple and intuitive, unlike so many properties. Plus Matt and Jenn were very responsive to our queries (and they didn't have onerous check-out requirements, again like so many other Airbnb properties). We would definitely return, particularly in the off-season, but then spring and autumn are our favorite times of year. Highly recommend.

Our stay in Gloucester was beyond amazing! A trip we have put off since Covid began but back in June we decided to make it happen! Sarah’s condo was beyond our expectations. Beautifully set up,homey, comfortable and right in the middle of the most beautiful views I’ve ever seen. We are from Annapolis, Maryland and I grew up on our bay crabbing … Gloucester reminds me of home. Everyone we met were so friendly, helpful and made sure we were comfortable. I’m a runner of 40 miles a week so my morning runs were filled with so much beauty from colorful leaves, to a sunrise I’ve never seen! Sailing is my thing so being surrounded by water, boats and of course the smell of fish … we knew our trip was extra special! We stayed specifically on Halloween for Salem fun and Salem did not disappoint! Helpful… a bar directly across the street from her air bnb! We hiked to the lighthouse early morning for exercise and its view did not disappoint either! Five star visit!

We absolutely loved this air bnb. The location was perfect, a 5 minute walk to the beach, 2 minute walk to a restaurant, a nice, peaceful backyard. The back deck was the perfect place for morning coffee and the fire pit was a great thing to have for the still-cold April weather. Michael was very responsive when we reached out with a very minor request. The house was clean, organized, and well labeled! Lastly the largest bed was comfier than our bed at home, I haven't slept that well in months. Highly recommend, we will definitely return.