Chebeague Island Inn

Chebeague Island Inn

You might have noticed Chebeague Island Inn on our list of ‘Hopeful Reservations’ in the Map & Menu sidebar – we’ve been wanting to stay at the inn for ages! As soon as I saw it come on sale via Jetsetter earlier this summer, I decided to book a night on the island as a reward after a particularly busy week (shooting four weddings and a rehearsal dinner in 8 days!) I knew it would be the perfect quick getaway, and it really turned out to be just that.

At the end of the 19th and beginning of the 20th centuries, hundreds of similar inns spotted the islands of Maine, but in the time since, most of them have been destroyed. Fortunately for us, the Chebeague Island Inn (formerly the Hillcrest Hotel) has been well preserved and maintained since it was rebuilt in 1920, and we were able to take full advantage of its sweeping views and classic decor.

We got to the island before our room was ready, and we were kindly invited to enjoy either the inn’s wraparound porch or the bicycles. Given that we were in full-on relaxation mode, we opted for the porch for a bit with our picnic lunches (from one of our favorite sandwich shops, Leavitt & Sons) and almost found ourselves lulled to sleep with the ocean breeze and comfortable wicker chairs. Somehow, we managed to escape the comfort of our seats and decided to take a leisurely bike ride around the immediate area. True to form, we ended up finding and enjoying some cups of Gifford’s ice cream at Calder’s Clam Shack – quite possibly the only place to get ice cream on the island. We eventually made our way back to the hotel, where our room was ready.

I had a feeling that I was going to be smitten with our room, and my intuition was spot-on. It was absolutely darling and I simply couldn’t stop saying so the whole time we were there! I’m not sure what I loved most – the bright white walls, floor, and bedding, or the pops of cheerful, colorful accents. Of the inn’s 21 rooms, no two are alike – they’ve all been uniquely decorated by local artists. The attention to detail and thought put into each room really shows, and it’s a somewhat secret goal of mine to one day see them all . . .

Our breakfast the next morning was incredible – Michael had a plate of eggs, bacon, and grits, while I had a breakfast scramble that left me oh so happy with life. Afterwards we took our final stroll around the property and paid one last visit to our favorite comfy porch chairs. Having just eaten a scrumptious breakfast, we could have stayed right there for hours watching life go by on the water. If we hadn’t had to get back to the mainland for work, who knows – we might still be sitting on that beautiful, restful porch!

Chebeague Island Inn Room

Chebeague Island Inn Maine

Chebeague Island Inn Rooms

Chebeague Island Inn Photos

Chebeague Island Inn Pictures


Chebeague Island Inn View

Breakfast at Chebeague Island Inn

Chebeague Island Inn Breakfast

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