Waterfront vacation rentals in Winthrop

We had a great time, the house was very clean and comfortable. It has beautiful views, and a nice park across the street. It is a quick drive to downtown Salem, which was nice. We definitely recommend staying here!

Our first trip to the Boston area couldn’t have been better! This Airbnb was absolutely perfect for our family of four. The bedroom I stayed in had its own balcony with a beautiful ocean view—ideal for peaceful summer mornings or warm, relaxing nights. The open-concept living room and kitchen gave us plenty of space to unwind after a day of exploring. But what really sets this place apart are two unbeatable features: first, you won’t find easier access to public transportation—there’s a bus stop just a 30-second walk away that takes you right into Boston. Second, the hosts, Milan and Anna, were some of the kindest and most helpful we’ve ever met. Their local tips made our stay even better. Great amenities, smartTV, updated shower, dishwasher, laundry, grill available to use, etc. Right next to the house is a beautiful walkway that stretches down the beachfront of Winthrop. We’re already talking about coming back as the Boston area is second to none!

Everything was perfect , felt right at home the beds were the most comfortable I’ve ever slept on ! Shower was wonderful /great water pressure.

I needed a special place for a special weekend. I didn't want to propose in a loud, busy Boston location. I wanted private, quiet and intimate. Thats what the photos felt like and I'm happy to say that was the exact experience. April is a perfect time with sunny weather in the 50's. We had a pleasant conversation with Susan in the shared driveway on our way to dinner. She recommended Seaport Grill, specifically the Chilean Sea Bass. It did not disappoint. Plus the Hammond Castle. It was an unforgettable weekend. She said Yes!

This place is a perfect Nahant beach get-away. We were there for a wedding over the weekend, and were so lucky to find Elyse's place! Elyse is a wonderful host, and she communicated everything in such a detailed manner that finding the place/checking in was a breeze. It poured rain all weekend, but the cozy, clean unit that is decorated beautifully and is so conveniently located to everything made us feel at home. The unit has everything you need - even a lovely deck overlooking Boston Harbor. Elyse was gracious enough to offer to turn on the hot tub for us while we were arriving, and she had great local recommendations. While we did not get to use the hot tub or go to the beach because of the rain, we hope to return and take full advantage of how special this place is again!

This was a perfect location for a long weekend getaway! Proximity to public transportation makes this place an awesome option for Boston travels, the ocean is absolutely gorgeous! I ran the Boston marathon on my visit and the hot tub was incredible for recovery! The bed is so comfortable and even though we didn’t cook anything, we easily could have! Having a washer and dryer in the unit available meant that I don’t have piles of laundry to do when I get home!

This truly was the best AirBNB we have ever stayed in. Diana was a wonderful host, no detail was overlooked and the location is magical. Definitely a 5 star experience.

We stayed over in Michael’s place for a small overnight girls trip (4 of us) and it was the perfect size! Beds were comfy, everything was clean, and Michael was very proactive in letting us know about checkin beforehand. It’s also in a great location, close to all of the downtown attractions but still in a quiet neighborhood. I’d definitely recommend this place and stay here again!

FAV SPOT!!! 2nd visit (2yr ago - we visit our college kiddos :-) views are amazing over the harbor out to the gulf of Maine... Easter so all kinds of weather - exciting New England! ;) Sunsets astonishing + rainbow! Gaby is so responsive, place is btr appointed/clean/stocked than home! right on any Qs/needs 👍 kiddos could even bake together :) temps 30s to 80! glad we brought swim suits + hats :) Wonderful to have a place to dig in the sand, find shells and jump in the waves :-) it was pre-season but rented dble kayak from awesome fellow who runs North Shore kayak :-) totally rec them! we love to paddle that peaceful gorgeous cove (pick your timing - not always peaceful... ;) also love: touch-aquarium in Glouc, walk to salt Island, Woodmans/dairy maid :) train to Boston/aquarium/see kiddo at university :) if any physical challenges chk w gaby bout the stairs she guided us last trip GPs did ok - thank you Gaby for helping our family to make wonderful memories at ur blessed place! 🙏

Tommy was great. He was easy to contact and communicated wonderfully. The house was set up for a guest with everything you needed for a comfortable stay. The furniture and beds were so comfortable as well as the welcoming feel. Plenty of spacious rooms. Even spaces you could have alone time. When they described the house on the ocean, it really is. This was by far the best Airbnb we’ve stayed at. Hope to rent it again next year. I can’t say enough on how comfortable the house is. This is the first house we’ve recommend for other people to stay at. Peg

Property was just as pictured, which I find extremely important. This spot is off the beaten path and quiet with a nice little walking bridge for a stroll. Close enough by car, to all the attractions of Glouchester when your ready to get out and about.

Super responsive hosts and a great place to stay!

We needed a place for our family to stay for a wedding nearby and this was perfect. Lovely scenery, easy to access, had everything we needed.

A great base while my child attended a sailing course at Duxbury Bay Maritime School. This is a lovely area. Bogs, salt marshes, beaches. The house was very clean and beds super comfortable. Sunset over the pond is beautiful ! Advertised as max 8 people though there is only bed space for 4. Having said that, there is plenty of space in the house for more people with air mattresses. Only other comment is that there is not much in the kitchen. Nespresso machine but no pods. No other coffee maker that I saw. Salt and pepper in the cupboard but nothing else. No pasta strainer. Small things that didn't overall impact our experience but worth mentioning.

Look no further for a central spot to enjoy everything Gloucester has to offer! Cozy home with the quintessential fishing port views. Short walk to shops, restaurants and many historical sites to enjoy. This home is perfect for families to gather and feel comfortable, safe and comfortable. Excellent value for location, amenities, walkable, and quiet!!! Beautiful home. Our family had our best Christmas Holiday ever. Kathy is an exceptional host.

This house was perfect for two parents and two grown children to spend Christmas week. The views were amazing, the setting very peaceful. The neighbors were very nice and welcoming. (Lots of dog walkers.) The temperature throughout the house could be regulated very well. Separate thermostats for upstairs and downstairs. The TVs worked great and there was comfortable seating for our group. The bedrooms were very comfortable and the bathrooms worked great -- plenty of hot water and nice amenities. The kitchen was very well equipped for any kind of cooking. As we were leaving, my wife and I said this was probably the first AirBNB we've stayed in to which we would happily return.

Great house! Loved all the ammenities. The host was very responsive if we had any questions and will definitely look at staying there again next time!

Lovely area, deer walk up to the property. Super clean, such comfortable lodging. Easy to enter, no lugging furniture up steps (sometimes makes a big difference), just unload and roll inside. All the amenities you’ll need for a perfect stay. Great restaurants very close. Would highly recommend!

We had a wonderful visit, from start to finish! Michael’s place was comfortable and clean and had everything we needed.

This comfortable apartment has a charming view of Gloucester harbor. It's location adjacent to a live theater and around the corner from Rocky Neck is perfect for entertainment and exploration. It's a five-minute car ride into the downtown, or if you're feeling a need to stretch your legs - it's a long, easy walk.

Had the opportunity to stay in East Boston. What a treat! The home was comfortable and had everything you would need. A very special shout out to our hosts. Never had a host as responsive and helpful. Thanks.

We stayed Thursday night through Sunday 4-2-25 thru 4-6-25. Almost everything was in walking distance. We tried a new restaurant every night, eating mostly Italian. We weren't to far from Quincy Market, we had brunch almost every day and did shopping. It is right across the street from the wharf and we had a beautiful view from the living room. We went to go and see the Red Sox game for opening day. Couldn't have asked for better weather and a wonderful place to stay. Any questions we had were answered quickly and they game us great recommendations for restaurants. We will definitely be going back again, rating was 5 stars! Anne Duran

The condo was lovely! Very clean, well decorated and great location. We are repeat customers and highly recommend. Karen is very friendly and is easy to reach if needed.

We really loved this location! We only stayed 1 night to sight see Salem for my kids' April break and Ryan's place was perfect. Private parking behind the house was a HUGE plus. When the weather gets warmer, it would be even more amazing since it's so close to the beach. Well described, very clean and little things like a K cup in the morning was a huge bonus ;-)