Our hope and preference is that everyone will stay right here on Chebeague Island! To help make that as easy as possible, we’ve put together a list of rental homes on the island for you to explore.

Staying on Chebeague is our top choice for our guests because it means you can truly settle into island time by enjoying the beaches, exploring the island, and soaking up all that makes Chebeague so special. And, selfishly, we would absolutely love having all of our favorite people nearby so we can spend as much time together as possible throughout the weekend!

One thing to keep in mind as you look through the rental list: many of the homes on Chebeague are classic, rustic New England beach houses that have been passed down through generations and have a wonderfully old school island charm. Many owners choose to rent their homes independently rather than through Airbnb or other rental platforms, so the listings can sometimes feel a little more low key than you might be used to. We encourage you to reach out directly to the owners by email. They are incredibly kind and welcoming and will be happy to share more up to date information, photos, and details about their homes!

We do recommend looking for and booking your accommodations as soon as you can. Chebeague is a popular summer destination, and many homes are already being booked for the 2027 season. We hope you’ll find a place you love and join us for the full island experience!

View our Chebeague rental list here!

We also know that staying on the island may not work for everyone, so we will likely be adding a room block in Portland as another option. That said, our preference is still for everyone to stay on Chebeague if possible, largely because of the ferry schedule and the additional travel time required to get to and from the island. We’ll share more details about the Portland option as we get closer!

Once you’ve booked your accommodations, please let us know so we can keep the list up to date and have a better idea of where everyone will be staying!