Apartment holiday rentals in Winthrop

My family and I loved our stay at Olga’s gorgeous house! We were there for five weeks with our two young sons, and it exceeded all our expectations. Not only is the space large and light-drenched, it’s nicely decorated and equipped with everything you could need. And the neighborhood is wonderful—a quick walk to the water with friendly neighbors. Olga was incredibly kind and helpful—the perfect host. If you’re looking for a large, comfortable space near the beach and not far from Boston, I highly recommend you check out her place!

Emma’s place was very well-located. A short walk to Parlor ski company (check them out if you want custom skis!); a short walk to the Metra (which was easy to navigate); a short walk to good food and fun bars (check out Renegades Pub for trivia on Wednesdays); easy Uber rides to…anywhere…and very close to the airport. Plenty of closet space; comfortable living room; and character with an old claw-foot tub in the bathroom. I liked the option of pillows on the bed and slept soundly during my stay. Emma had food recommendations posted on the fridge and they were spot on! Very good value for the price! 🤙

Stephanie’s place is beautiful and matches exactly as she listed. The location is very convenient when we visited Boston the past week. Stephanie is also very friendly and proactive about instructions. Highly recommend. Thank you for your hospitality and sharing your beautiful home Stephanie!

The area was quiet and safe, very walkable, and reasonably close to the Red Line downtown. Hosts were communicative, accommodating, and generous. The complimentary snacks left for us were welcome after our long day of travel and late check-in when most restaurants were already closed.

We had a great stay! The place was cozy and comfortable, located conveniently close to both the airport and the city center. The backyard was a lovely bonus, perfect for relaxing. The host was very kind and responsive whenever we had questions. Would definitely recommend it to others!

We had the best weekend. This Airbnb is a great size for 2 people. Clean, cozy and you have everything you need. Close to the city but you’re right by the ocean. Great restaurants nearby. We stayed to celebrate our engagement and attend a concert at Suffolks downs. We would definitely visit again. Easy to find and easy to get into. Nice and quiet neighborhood.

The place was beautiful. The view was amazing. Only downside is we came in during road construction and even with that is wasn't too bad!!

We stayed here in mid-June and loved it! The inside decor was so cute to match Salem’s aesthetic. Everything was very clean inside too. The backyard was private so it was nice to enjoy coffee outside in the mornings. The best part of this place is the location. There were some days we didn’t even move the rental car because we could walk everywhere. Having the on-site parking was also a plus! I cannot recommend this place enough. I would definitely stay here again.

Steve and Nancy were wonderful, gracious hosts. They allowed us to check-in early, gave great information about the area, and were awesome communicators from the time we booked until we checked out. The apartment was perfect for my nephew and me. It was a restful place to return after long days of sightseeing and lots of walking!

Great place. Just a bus ride into downtown and to historical sites. Comfortable space. Great host

We really loved this spacious studio. The landscaping was so beautiful it really added to the experience and a sweet family of bunnies were hopping in front of the windows. The bed is very comfortable and the giant TV was very nice too. We sat on the couch and looked out at the ocean and filled our days with trips to the beach, playground, and local restaurants. It was a fun little staycation that we will most likely book again!!

I’ve stayed in downtown Boston several times. This stay on the East Side was the best ever! Loved walking to the ferry and seeing the cityscape at night. Will never stay in Boston proper again. This is so much more fun. Great host and brownstone. Parking is not bad. Just use the app recommended by host. Book now! You won’t regret it!

We enjoyed our stay here! the neighborhood was very nice and we felt safe. The restaurants and coffee shops in town were close and very good. We enjoyed the dining area/sunroom in the home and found it very peaceful. The hosts were in contact with us and checked in to see if we needed anything before we left. Overall, a great stay and a nice spot close to Boston.

Kemi was a wonderful host and this place is superb! Everything exceeded our expectations. It was about a 10-minute walk to the train to get into Boston, which was perfect. And coming in from the rain to a welcoming, cozy home was the best. We hope to stay here whenever we may come to the area again! Thank you so much for the special touches and everything, Kemi!

Perfect place for Brookline area. As described. Beds are comfortable. Pristine condition. Jan is an awesome communicator and accommodating. Extremely happy! I’ll stay again when in the area as my first choice. 6 stars out of 5.

We went to Salem for 2 nights for a rehearsal dinner and wedding. This home was perfect for the multiple events we had to get ready for! The upstairs is completely private. The hosts truly thought of everything! They have everything we could have needed and then some: warm blankets, toiletries, wine glasses, hair dryer, etc! It was VERY clean. I do not think I saw a speck of dust in the entire place. The bed was comfy and we were able to rest between events. I unfortunately did not get to meet the hosts in person due to our crazy schedule for the trip, but they were incredibly kind and attentive through chat. Everything was walkable from their home. We even took some time to do a late night walk in the neighborhood and it was beautiful and quiet. Check in was easy and flexible. Would absolutely stay here again!

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!

Our stay was wonderful, everything was very clean and cozy. We had plenty of room for our group and was very convenient going to and from Boston for all of our activities. The host(s) were quick to respond to any questions or concerns we had. Thank you!

Fantastic place, beautifully appointed, great location. Highly recommend staying here. Everything is within walking distance. Loved the rooftop deck and jacuzzi. Probably the most comfortable beds, linens and pillows we’ve ever experienced in our many air bnb stays. Extremely comfortable.

The unit we rented ended up not being available at the last moment but Jonah was able to find and arrange comparable accommodation set away

Clean and easy to check-in. Owner lives just downstairs and takes great care of the curb appeal of the house. Beautiful gardening. Always responsive and easy to work with. Quiet street.

Everything was absolutely exceptional! My parents stayed here for two weeks and had a wonderful experience. The hosts were incredibly kind and responsive — they replied to our messages and requests immediately, which made everything so easy and stress-free. My parents left extremely happy and are already talking about coming back. Highly recommended!

We felt right at home in this gorgeous place, watching the tide roll in and out over a beautiful bay. That magical night watching the lunar eclipse from a warm, jetted jacuzzi while the wind blew gently around us and the lights reflected off the water will never be forgotten. Thank you, Anthony, for a really memorable and beautiful experience.

Annique's place is a second floor flat in a quiet street not far from the "T" and grocery stores. The flat has a beautiful wooden floor and spacious bathroom. For me, the high point was having an office space with a standing desk - I loved it! The amenities Annique provides shows she is an extremely thoughtful host and is very responsive. Definitely an excellent place to stay..