Waterfront vacation rentals in Winthrop

Ideal location walking distance to shops and restaurants. Unit provided everything we needed for our stay very much recommend this apartment to anyone planning to travel to Rockport

What a lovely place to stay in Rockport. Great location that’s super walkable to the shops, cafes, galleries and beaches of Rockport; I took the train and did not need a car during my visit. The apartment is great, with a comfy bed, smart TV and a well-equipped kitchen for preparing meals when not dining out. And a great little patio overlooking the harbor. Gigi was a very helpful and responsive host. Thank you!

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!

This was the perfect place for our family. Comfortable bedrooms and twin beds for the kids. Right across the street from the beach and a playground. Would definitely stay again if we were in the area.

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!

Great place to stay. Super accommodating and friendly to do business with.

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!

Stayed with a friend in April and it was perfect for our needs. We had a comfy room each and pleasant living space and patio. Bathroom was small but it didn’t matter. Shops and cafes and harbor all very close walk away. There’s a good place on Tuna Wharf to hire ebikes and kayaks to get around, too. No need for a car really. We arrived on the train to Rockport - station is about 15 mins walk away and there’s a good grocery store next to the station.

Perfect location for everything you might want to do in Plymouth. Great restaurants are a short walk away, and so is the beach . The home is perfect—great private patio, a hot tub, outdoor kitchen, perfect for a quiet getaway or with guests. Keeping this place on my wishlist for future visits.

Gabriela's beach house was so beautiful and the views were unbelievable! Right on the beach and the house had plenty of space for my family and I. She was very responsive as well! I would definitely stay again!

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.

We stayed at Jenny and Thom’s for a family reunion weekend in Newton where the festivities were at my sister’s house who lived nearby. The home was perfect for what we needed . It is very cozy, nicely decorated, very clean, and well equipped. The view from the back is so peaceful and we even saw a swan! The beds are very comfortable and the bathrooms are squeaky clean. Directions for care of the home are very clear - and little details like labels for the lights were helpful. Jenny was always available if we had any issues but we had none. We would stay again!

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.

James was an excellent host for my family and me. We thoroughly enjoyed the place and its beautiful surroundings.

this place was perfect for my friends and I to stay in while my brother was fighting for cage titans. everything is in walking distance and I'd definitely book again!

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!

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.

I booked this Airbnb as I was attending a wedding at Piers Park in East Boston! It was so close and it was only a 6 minute walk away! Upon arriving Jay, the property manager met us at the Airbnb to go over how to run and find everything in the Airbnb, which I found to be super helpful! Not only was it helpful, but it was so nice to meet Jay. He was so sweet and he gave so many great recommendations! This Airbnb had it all! I truly could not have asked for a better place to stay ☺️

A fantastic way to spend a long fall weekend in Massachusetts. The apartment was cozy and convenient, and we loved exploring Rockport. Top tip: eat at Roy Moore’s. A lot.

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

This is the second time we stay at Zachary’s listing on Thanksgiving Parade day. We are hoping to make it a tradition as his place is luxurious, well outfitted with wonderful furnishings and an AMAZING location! Zachary was extremely responsive, friendly and helpful and I would highly recommend staying with him again!

I pride myself on finding fantastic accomodations to match fantastic travels, and this was the best lodging location I have ever found. So special to stay right out on the peninsula/wharf amidst the charming, narrow lanes of seasonal gift shops and restaurants, with water all around us. The unit is super clean, nicely decorated, well supplied (including a basket of upscale snacks and handwritten note), and private. A peaceful little nest from which to watch the Atlantic, the beautiful town, and the harbor activities. Really hard to tear yourself away from the amazing views out every window. Water lapping the wharf will send you to a peaceful sleep. Nighttime wanders on the wharf were super quiet, gorgeous, and romantic. Catherine also very kindly offered us to stay past check out time when the opportunity arose, allowing us extra hours of fun! Recommend her suggested walk to The Headlands for photo op of the unit. It's crazy it's practically next to the famous Motif #1!