House holiday rentals in Winthrop

The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.

Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.

Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!

Brad was very friendly and helpful. Beautiful home!

I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽

Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!

Scott was very easy to communicate with, and he was very nice. They were so thoughtful and even left us a dozen eggs from their backyard chickens! The place was spacious and peaceful. Check in and checkout process was very easy!

Absolutely incredible stay. The host was very helpful. The house is absolutely beautiful, and the lake is stunning. The basement was so so fun- darts, ping pong, billiards, and more games. We miss the house already!

Amazing spooktactular!! Perfect location to get to Salem. So many adorable decorations, we enjoyed every minute of our stay. The road is very busy on the front of the house but the very private patio makes it worth it The side street is quiet with easy parking. Using the side door next to the drive makes bringing luggage in a breeze. The Witch house is the place to stay if you want a fabulous Salem vacation!

We had a fantastic stay at Johnny’s place. The house is great - comfortably enough space for a family of 4 and well configured, well-located 5 mins walk from great coffee shops and restaurants in Charlestown and only 20 mins walk from the North End and central Boston. Johnny was extremely accommodating. Highly recommend!

Very quaint. Literally felt like my own apartment. Small yet big. Nice spacious open floor plan. The private parking was definitely a huge plus. The perfect distance from just about anything you want to do in the city.

Stayed here for 10 days in late November. My mom was transitioning from the hospital to rehab and then to her home. I worked all day everyday getting her place ready. John's Place came to be known as My Sanctuary at the end of the day. Very comfortable and very quiet. And John is a very nice, accommodating, compassionate guy. He asked about my mom everyday. I will definitely stay here for my next trip to the Boston area. Thanks for everything, John!

Greg was very nice to set up a welcome message for us and leave some candles on the counter for my kids. It has a lot of space, 3 bedrooms 1 big living room and kitchen, lots of furnitures and storage too. We were also given the permission to enjoy their lovely backyard, swing and the slides.

We had a fantastic stay at Sue’s place! She was incredibly responsive and attentive, clearly committed to making sure we had the best experience possible. The home itself is perfect—clean, comfortable, and thoughtfully set up—and the location couldn’t be better. Honestly, there’s nothing we’d change. We had a great time and would absolutely return. Highly recommend!

Beautiful home and well located to explore. Rewan is an amazing host! Truly exceptional

Great home and location. 15 min drive to downtown or walk over to the T for even easier commuting. Quiet and safe neighborhood. From Salem to the Cape, nothing is to terribly far.

This airbnb was really beautiful and well-stocked. For a family of 4 adults, it served us well. Flavia was very friendly and responsive. The location is perfect as it's just about 10-15 mins from BOS. You can also walk to a shopping centre right across the street. The neighborhood is calm and peaceful. Note that this is a half basement style space. My dad is 6 feet 1 inch and the height of the place was not favorable for him.

I had a wonderful stay! The place looked exactly like the photos—clean, serene, and thoughtfully put together. It was the perfect spot to relax. Kimberly was very responsive and provided great local recommendations. Would definitely stay here again!

Great spot! Perfect for a one night getaway we needed. Very clean, appears as advertised! Sonam is a very responsive and friendly host as well, which was so helpful.

This is my third booking at Kay's place. That should say enough when there are many other choices.

This is a beautiful home! It had everything we needed and then some. Beautiful view from most of the home. Master bedroom view and large balcony off of the kids bedrooms to see out as well. I hate using a small at home gym set up but this actually provided a decent workout. No large weights though. My kids thoroughly enjoyed themselves both of my older kids left their own raving reviews on our checkout sheet. We enjoyed the beach, doordashed lots of food, cooked in the kitchen, watched movies in the basement, enjoyed mocktails on the patio, I will forever miss that kitchen ! Definitely a wonderful stay!

I wanted to take my mom to the Boston area and settled on just south of Boston I was lucky to come across Asha’s Airbnb listing. We had the most wonderful relaxing enjoyable stay far better than any hotel in the area . The house is exactly as stated super well appointed. Asha thought of everything to make guests comfortable and we truly enjoyed three days of beautiful sunny weather… So much so that we did not even set foot in Boston. Asha, thank you for a five star stay and we will definitely be returning maybe even this summer

Lionel’s place was spotless and was in the perfect location! The easy parking was a huge plus too. Lionel was incredibly accommodating and responsive, and we will absolutely be staying here again next time we go to Boston!

The place suited our needs very well. Hosts were easy to communicate with. Great space for a large group visiting Boston.