Holiday rentals in Gloucester

Fantastic stay. So much space inside, and absolutely gorgeous sunset views. Super clean and comfortable. I definitely recommend!

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!!!

Staying in this guest house was really great for me, my wife and our two small dogs. The front of the home overlooks are beautiful marsh. The area is very peaceful, and it's next-door to a quaint little park, and a few minutes walk to a private beach.

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!

Great place to stay! It felt like home. Our boys enjoyed the book selection & board games. Everything is in walking distance & truly grateful our dog was able to join us. We were in town for a soccer tournament so we weren’t able to see everything that was around but enjoyed the recommendations. We had dinner at the barn & picked up coffee and chocolates the next morning at Godiva and explored the river walk.

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.

Sean’s space was perfect for our visit to the area! We will definitely come back to stay again :)

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!

We absolutely loved this air bnb. The location was perfect, a 5 minute walk to the beach, 2 minute walk to a restaurant, a nice, peaceful backyard. The back deck was the perfect place for morning coffee and the fire pit was a great thing to have for the still-cold April weather. Michael was very responsive when we reached out with a very minor request. The house was clean, organized, and well labeled! Lastly the largest bed was comfier than our bed at home, I haven't slept that well in months. Highly recommend, we will definitely return.