Pet-friendly holiday rentals in Winthrop

We enjoyed staying at Karen’s! It was a super clean space which we really, really appreciated. The neighborhood is peaceful and quiet. Super easy to check-in and check-out. Karen is also super responsive and proactive which was great! Only bump in the road was that we unfortunately had to deal with a water leak issue which was stressful but Karen did what she could to be as helpful as possible. It was fixed shortly after reporting. We appreciated that Karen coordinated maintenance so quickly in a way that was accommodating to our schedule. Overall we are very pleased and would definitely recommend!

Nice apartment for me and other two friends. Thanks for Jovan being patient to answer all my questions. But the disadvantage is that the location was too remote which you barely find transport reach to Boston downtown.

Loved our stay. Perfect for our extended family and way more reasonable than Boston hotels during graduation season. Spot on descriptions. Shelby was very responsive. Kind enough to offer access to pantry (e.g. sugar, honey, tea etc) and the garage parking is a HUGE bonus for Southie.

Great place. We loved the location and the surroundings. Wally was you receptive and proactive. Everything we needed was available. The instructions and local information was great and even though we had a plan of things to do, it provided us a couple of awesome ideas for our down time. Would definitely stay there again and would recommend. Thanks Wally.

The location was perfect and relatively close to everywhere. We liked the 3 levels so that we each had some private space. Wonderful home to play board games in the dining room, watch documentaries on the Big Screen and nap in the afternoon. Very comfortable/livable space.

We were very comfortable as a 3 generation family. Thoughtful details and clear instructions were very helpful and appreciated.

Beautiful home. Perfect for a couple days in Boston. The home had everything we needed. Hosts always responded quickly to questions. Easy walk to local transportation.

We really enjoyed our stay. Such a Warm and cozy home. Elizabeth was easily reachable whenever we had a question. Would highly recommend her cozy home. Thanks Elizabeth

Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!

I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽

We absolutely loved our stay at this home! It was extremely clean, cozy, and beautifully prepared — every detail made us feel so comfortable and welcome. You can truly feel the love and care the host put into the space. It felt like a warm home from the moment we arrived. We are already looking forward to coming back again. Thank you for such a special experience! 🙏✨💕☀️

The check-in process was so smooth and finding the place was super easy! The house was absolutely gorgeous and accommodating for us to stay the night. We wished we could have stayed to enjoy the amenities that were part of the campground! The location was perfect for us to be able to go to our concert the night of check in! We will definitely be back in our future travels!

My stay was comfortable and met my expectations. I’d come back the next time I’m in the area!

We stayed for three nights to visit the surrounding Cape Ann area. Ian’s place was fabulous - private, spacious, and fully equipped with amenities including a BBQ stove by the pool. Space is larger than the pictures looked like and furnitures were of high qualities. Highly recommended for anyone travelling in the area!

Hanky’s place was great! Awesome location with lots of things to do and places to eat. The apartment was clean and had all of the necessities. Extra bonus was the lunch we had waiting for us when we checked in. Only down side was how expensive parking was but that’s out of anyone’s control.

The home was so lovely and comfortable - perfect for our family. It had so many amenities, and comfortable sleeping spaces. It looks exactly like the pictures. We will definitely return!

We felt right at home during our stay at Monica's place. Monica always responded quickly to any questions we had and was kind enough to share some recommendations for us to visit in Boston and Salem. We truly enjoyed our stay. Thank you for everything Monica!!

Greg was very nice to set up a welcome message for us and leave some candles on the counter for my kids. It has a lot of space, 3 bedrooms 1 big living room and kitchen, lots of furnitures and storage too. We were also given the permission to enjoy their lovely backyard, swing and the slides.

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.

Such a beautiful and spacious place to stay. Perfect for families! We had such a great time and loved how it’s close by to the ocean. Will love to stay there again!

Lovely well stocked place on a quiet street, and yet it is so close to the city center! Just a 10 mins drive to BOS airport. The first floor layout worked well for my parents who have weak knees. Just note that there are about 5 steps to get into the apartment. Tanya was very responsive and friendly.

This was exceptional. Becky's AirBnB is absolutely STUNNING!!! I think, quite honestly, it was the most beautiful accommodation I've ever stayed in. Becky thought of EVERYTHING, from the delightful snacks and beverages, to the notebook of fabulous restaurant and activity recommendations, plus the elegant and soothing seaside decor! Some of the plusses include a cozy gas fireplace, a great gas range to cook on, and an outdoor grill! We cooked up and grilled up some fabulous feasts during our stay! But the real treasure here is Becky herself. Although she grew up in Salem, she says she inherited her mama's Southern hospitality, and it definitely shows! She is warm and joyful, and my daughters and I feel we have made fast friends with her. We truly look forward to visiting Becky again!

This AirBnB was exactly what I would hope for. It was beautiful, fashionable, very clean, organized, and in a great location. The neighborhood is super clean and safe. There is a bus stop right across the street, and I was always the only one waiting there for the bus, so it isn't like a bunch of traffic is right there. I recommend that you get a Charlie Card as ASAP because then that bus station across the street opens up many opportunities for easy and affordable getting around. The hosts were very kind and helpful, very responsive and super easy to communicate!! :) Good choice!!

Easy to communicate with and perfect access to Boston area. Thanks!