Family-friendly vacation rentals in Winthrop

This beach house worked perfectly for our stay!! The access to the beach is easy and the accommodations perfectly welcoming! The co-host could not have been more welcoming and helpful!!

This condo was perfect for what we needed. Just two bedrooms, a kitchen and living room, so we could relax in between walking adventures. I wish I had come across this back in the fall when my daughter was playing soccer for Northeastern because the soccer field is literally across the street. There is a nice walking trail about a quarter of a mile away. We really liked Coolidge Corners. Easy to get Ubers. The place was perfect and comfortable and easy to get in/out.

The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!

Great location and nice and clean apartment. Host was also really great, provided good instructions and answered quickly to any questions we had. Overall, great place and great host - highly recommend!

Alex placed us in another, upgraded apartment of his due to a last minute water issue. It’s clear he went above and beyond so we didn’t have to scramble for another place to stay.

Apartment was clean, comfortable and priced well. It was the perfect size for family of three. Loved the outdoor space and great location. Marblehead is stunning. Host is excellent

Wonderful getaway in the woods, but close to restaurants and shop in Rockport. We loved being greeted by the dogs and the hiking trails right outside the front door are amazing.

We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.

Had a wonderful stay with my friends in Boston. The rooms and living spaces were very comfortable and clean. Michelle was very reachable and responded quickly. Would recommend this home to anyone.

We loved Ellen's place from the minute we walked in. It was warm, welcoming and had everything that we needed for a week's stay. The house/apartment is set on a quiet street set in the woods but a very close drive to Concord where we spend most of our time sightseeing. Helen's is the best restaurant to try in town. Ellen and her husband Kevin were there to welcome us and answered any concerns we had about the place. Her place is very comfortable with a large living room to relax in, a kitchen to cook in and a very comfortable bed to sleep in. I give her place 10 stars and more and I recommend it to anyone who is staying in Concord. Thank you Ellen for the wonderful stay and we look forward to seeing you again

Wonderful experience at Johanna’s house. We had the whole first floor and it was everything we had hoped it to be. Accommodations were generous and available. The home is located right in Beverly Mass and also walkable to the water. We will be back.

Mark was a great host. The location was close to our destinations and Boston itself. The place was as large as advertised. Having two bathrooms was a positive.

The home was in a very nice and quiet area of town with groceries, gas and restaurants a short walk or drive away even in during busy hours of Boston traffic. The home was actually larger than expected with two full bathrooms, one on each floor. Everything was clean and ready for us with a well equipped kitchen and filtered water. There was a nice booth area to eat as well as counter seating and a dining room. We only had three in our party, but you could comfortably house a much larger family in the rental. We have a few more trips planned to Boston this year and will book this first if it is available, would like to stay again.

Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!

We had a great time - beautiful house in a terrific location. Super convenient for Phillips Academy if that's why you're in the area. Nancy was very attentive (and actually lives in an apartment downstairs) so was able to do lots of nice things for us like bake us a coffee cake and make floral centerpieces. Thank you!

Smaranda was outside when we arrived, she greeted us and since it was around dinner time she offered some recommendations for dinner. It had been quite windy that day so the pool and hot tub had some leaves and debris in them. She was very apologetic (obviously not her fault, we can't control Mother Nature) and was very attentive and worked hard to get both the pool and hot tub ready for us to use. She showed us how everything worked and the instructions were clear and easy to follow. We used both the pool and hot tub after we got back to the space after dinner and they were both very nice and relaxing. We enjoyed our stay and everything went as planned. We would definitely stay again if Smaranda would have us! Stacy and Ray

We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.

This was such a a delightful place to stay. The surroundings were so beautiful and calm. We were greeted by turkeys, and a mother and newborn deer crossed our path as we left. The hosts, Susan and Mark, were friendly, attentive and accommodating. I would certainly come back in a heartbeat.

Our second time, weeklong stay! And we hope to do it again next year. Just simply meets our needs very well. It's a joy to stay here!