Vacation rentals in Winthrop

Judy was a great host, very gracious and the place is beautiful. We loved walking around the area and would love to come back!

Doug's place was absolutely stunning and cozy. It was exactly as depicted in the photos. This wasn't exactly an issue but perhaps worth noting that parking can be a little tight due to the cluster of homes. However, we didn't have any problems with navigating the streets. All in all, it was very peaceful and the design of the home was very inspired. Doug was also a fantastic host and very communicative, providing recommendations and very clear instructions. I've bookmarked his place for a future visit.

Frank went above and beyond to communicate check-in instructions, rules of the Air BnB, had all the thoughtful amenities for a slumbo! Definitely an ideal location for nicer weather with the location! Unfortunately the weather hindered the ability to fully enjoy this experience with the water so close! Would book again with better weather!!!

Courtney & Chris were amazing hosts! They went above and beyond to answer all our concerns prior to our stay regarding public transport to Boston for the marathon. The house was awesome, with the beach only blocks away. We had an excellent experience & we're so grateful for our hosts and this beautiful lodging.

We absolutely loved our stay at Ryan’s place! The home was beautiful, spacious, and pristine—just like the photos. Ryan was a wonderful host from booking to check-out, making everything easy and welcoming. We especially loved the location, with the beach and great local restaurants just a short walk away. We would definitely stay here again!

Gretchen’s house is a charming, two-story one on a very nice and quiet little street. The furnishings are pretty and tasteful, and there is comfortable living room furniture, as well an excellent beds and pillows. Our favorite thing was its location, within very easy walking distance from a gorgeous park and beach. Downtown was also reachable via a short walk. We did some of our own cooking and found everything we needed. Gretchen was an especially nice and responsive hostess. If we were lucky enough to get to Rockport again, I would want to stay there.

Our stay at this lovely Scituate Coastal Retreat was fabulous. The house was immaculately clean and the decor was perfection. The common areas were cozy, but spacious and the kitchen was well stocked with any tools/utensils we needed. Beds were comfortable and our party of 4 adults had plenty of room. The hosts left great suggestions for local dining and the house was only a 2 min drive (15min walk) to downtown Front St restaurants and shopping. Host Andrew was very responsive and wonderfully accommodating, allowing for a later check-out when requested. We were staying in the Winter, so perhsps check out time may not be as flexible in the warmer months. Check-in & check-out was a breeze! We hope to rent this property again. Thank you Andrew & Madeline!

This house is perfect for the space / location. Not many listings with hot tub and still with great distance to things/beach. A very family friendly space / very ideal for large/multi family based on the kitchen/dining and outdoor areas. Note he is also transitioning/updating furniture which I think will help a lot.

Our stay in Gloucester was beyond amazing! A trip we have put off since Covid began but back in June we decided to make it happen! Sarah’s condo was beyond our expectations. Beautifully set up,homey, comfortable and right in the middle of the most beautiful views I’ve ever seen. We are from Annapolis, Maryland and I grew up on our bay crabbing … Gloucester reminds me of home. Everyone we met were so friendly, helpful and made sure we were comfortable. I’m a runner of 40 miles a week so my morning runs were filled with so much beauty from colorful leaves, to a sunrise I’ve never seen! Sailing is my thing so being surrounded by water, boats and of course the smell of fish … we knew our trip was extra special! We stayed specifically on Halloween for Salem fun and Salem did not disappoint! Helpful… a bar directly across the street from her air bnb! We hiked to the lighthouse early morning for exercise and its view did not disappoint either! Five star visit!