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!

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.

Great host! Super responsive and accommodating! Would definitely stay here again. Thank you, Venus!

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

Our rental was roomy with 6 adults and slept comfortably with bedrooms were big and roomy. The coffee station was great with everything we needed. William was there to greet us and allowed us an early check in to drop off luggage before enjoying the area. Lots of towels and toiletries. The place was very clean and enjoyed the snacks. Thanks.

We had a great stay—perfect for our quick family trip! The home was incredibly clean, cozy, and well-stocked with everything we needed, from a pack ’n play to extra towels, bed linens, and kitchen essentials. Marybeth was wonderful to communicate with and shared some great local dining recommendations. We were very happy with our accommodations and would absolutely stay again!

My wife and I had the pleasure of staying at Darryl’s place for our honeymoon, and it was absolutely perfect. Darryl was incredibly kind, welcoming, and a fantastic communicator throughout our stay. He provided us with amazing recommendations for local sights and restaurants, which really helped make our trip special. The space was clean, comfortable, and had everything we needed for a relaxing getaway. We couldn’t have asked for a better host or a better experience. Highly recommend!

My family and I were fortunate enough to spend the thanksgiving holiday here. It was the perfect space for a group gathering. Would highly recommend!

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!

Beautiful house in a lovely quiet neighborhood. Kitchen was amazing! Very walkable to Bearskin Neck and Old Garden Beach. We had a few little glitches the first night, but Rachel was very responsive and everything was perfect within 24 hours. Would absolutely be happy to stay there again. To future guests: Rockport is light on grocery stores, so even though most things are walkable, for groceries you might want a car.

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!

We had a fantastic stay at Johnny’s place. The house is great - comfortably enough space for a family of 4 and well configured, well-located 5 mins walk from great coffee shops and restaurants in Charlestown and only 20 mins walk from the North End and central Boston. Johnny was extremely accommodating. Highly recommend!

Fabulous location with great recommendations. The “treats” left for us were a welcome added bonus! Thank you!

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.

We stayed at Tanya’s place during our trip to Boston and Salem, and I highly recommend it. The home was spotless, charming, and located in a quiet, peaceful neighborhood. It was also pet-friendly, which was a huge plus for us. Tanya was incredibly responsive and helpful, offering great local restaurant recommendations and answering all of my questions quickly. The convenience of on-site parking made our stay much more relaxed and hassle-free. A wonderful stay overall!

This home was very cozy and beautiful! We had a Wedding to attend at the Nantasket Beach Resort and this was only a 5 minute drive. We only stayed one night but would love to bring the whole family back for a beach vacation. Wonderful host, great communication, easy check-in and check-out.

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!