Waterfront holiday 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

5 stars! This stay was everything we hoped for and more. The host was incredibly responsive and made the entire experience smooth and welcoming. The home itself is beautiful, spotless, and perfectly maintained. The view of the Motif #1 was absolutely stunning—such a special treat to wake up to each day. The bed was super comfy too, which made our stay even more relaxing. Highly recommend!

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.

It was even better than we expected. Location was convenient, house was beautiful and exceptionally clean. I'm OCD so this was big for us. She had an informative booklet on the counter when we arrived. She was great with communication. We wouldn't hesitate to go back someday.

We had a great time in Nahant and will definitely be coming back. B’n’B was very cozy and homey. We loved the porch and being able to use the grill, we used it both nights we stayed. The hot tub was also super easy to use and was perfect after a day of walking around Boston. Elyse also had bikes that we used to go for a trip around the island. It was a wonderful stay!

I can’t say enough about this beautiful home in Rockport. The view alone was worth every penny, but the comfortable and stylishly furnished space made it the perfect getaway for our family. Andree gave us great recs for dining, activities etc and was available when we had a question about the property. Already looking forward to another family trip to this lovely spot! It’s truly a gem.

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!

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.

What a treat to spend a couple of days at this wonderful home. The house itself is very nice, comfortable and well stocked, but walking out to the back deck and seeing the river with all of its wildlife was amazing. So peaceful and quiet, a great place for a morning coffee or afternoon wind down. I will definitely be back, highly recommend!

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.

The home is beautiful! The view and neighborhood are amazing! We felt like we were in a movie. It was peaceful and quiet and had things to do to enjoy a nice evening. Definitely will be back!

We absolutely loved Peter and Sally’s house, especially the front porch. We spent all of our time out there watching the world go by and taking in the beautiful view of the water. The house was clean and incredibly well stocked with kitchen and bathroom supplies. The beds were comfortable and the living room was great for family movie nights. The little beach across the road was perfect for our quicker beach trips (we have an 11 month old). I was worried about noise from the road but traffic really dies down at night and we hardly noticed it during the day. We thoroughly enjoyed our time and would stay here again!

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.

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!

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 ☺️

Spiro was a great host, he was able to accommodate us pretty last minute and it turned out to be such an amazing place to stay. Perfect size for our small group of 4, and plenty close to be able to walk into town. Over just a great experience. Thank you again Spiro!

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.

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.

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!