Waterfront vacation rentals in Chebeague Island

The apartment is beautifully designed, spacious, relaxing, and comfortable. What more could you ask for? We enjoyed our 3-night stay. Read some of the assembled books on birds and enjoyed delicious food at the local restaurants. Alice was a gracious and responsive host. You will truly love staying in her apartment!

The Crow's Nest was a lovely apartment with a great view of the city from the rooftop. The photos and description of the apartment matched the actual experience. Kathy was super responsive any time we reached out to her. She also gave us a fabulous list of recommendations for the area including restaurants, coffee shops, bakeries, and local hikes.

We would give this Air B&B even higher ratings if possible. It is one of the cleanest, prettiest and most comfortable one we have stayed at in our years of renting. The bed is amazing and we slept so well each night. It is now listed in our favorites and we look forward to returning.

In short, a unique experience where we met a few extremely friendly people. The property has amazing views of the harbor without noisy working boats. We would out this at the top of our rental experiences.

Jennifer's place is so interesting, clean and tastefully decorated! We enjoyed our stay very much and definitely would return there, as many guests do. Be sure to check out the wonderful nearby Salt Water Cod Cafe and the many Maine-made things from Seaside Creations on the road to the Giant Steps on Bailey's Island. Also, the chocolate from Jennifer's candy store up the road is really good. Thank you Jennifer for making this experience possible!

Adorable, idyllic, comfortable, serene. Couldn’t have asked for a better spot for our Maine Minimoon! Some places have 5 stars and aren’t really legit — this is not one such place. Hillary’s place fully deserves ⭐️⭐️⭐️⭐️⭐️. We look forward to staying again soon!!

These accommodations were perfect! Overlooking the Casco Bay harbor, the view was even better than depicted in the pictures. The condo was meticulously clean and very well appointed. The beds and pillows were so comfortable we slept even better than we do at home. The location could NOT have been better! It overlooks Portland’s old-town shopping district, and is easily walkable to all of the best restaurants in town. There is a beautiful walking trail just up the street, and you can easily catch the ferry to the islands from this location. It is convenient, beautiful and welcoming.

We had a lovely night at Audray’s place! The location & the views exceed expectations. It was clean, cozy and inviting. Edited to add- not reducing stars for this because we enjoyed the accommodations, but I want other travelers w/ pets to be aware: Audray reached out 24+ hours after we checked out to say her cleaning person reported “an excess of pet hair on furniture and linens than her washing machine could not handle”, and requested we mail her an extra $50 to cover special laundering. We sent $75 on platform instead as we were shocked and sorry to hear this. We found it surprising b/c were in the condo only 14 hours, we immediately covered the furniture w/ pet covers (we brought our own) upon arrival, we covered the beds w/ our own extra top sheets to protect the quilts from pet hair, & we do not let dogs sleep in the beds- we bring pet beds. We have only received compliments on cleanliness & exclusively 5 star reviews from hosts over 7 yrs and 23 stays all w/ multiple pets.

Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!

We love Harpswell and Timothy's home is a real gem. The house is beautiful and so comfortable! The view from the deck is absolutely amazing. We had a great week--we especially enjoyed kayaking. Timothy was so friendly and answered all my questions. We hope to return!

a wonderful place to stay.

It's a beautiful, little house, perfect for our needs. Great view from the backyard over the water. Being close to Rt 1 made all of the places we wanted to visit very accessible. The binder with places to eat and their menus made things much easier. When visiting the Bath area we would certainly stay here again!

Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!

Thoroughly enjoyed our stay! We unexpectedly had beautiful cloudless days most of the week. Great location & easy to get to the Harbor and Southport both of which we enjoyed! Recommend the Carriage House for a really top quality meal as well as Blue Moon Cafe (good lobster roll) which was one of Shirin’s recommendations. Would totally stay here again!!

We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

fantastic stay. clean and well equipped. the lake is even more beautiful than the pictures! Roman was very responsive and went above and beyond in providing helpful information about the area and place.

Unit was very clean, situated in a quiet residential area and within walking distance to many of Portland's best bars, restaurants and attractions. Host was communicative and provided clear guidance on check-in/-out procedures and offered up suggestions to local attractions. On my recommended list - dinner at Twelve (one of the best restaurants in the US, IMHO); on-site food truck tacos washed down with a Hazy IPA at Bellflower or Austin Street Brewery; an everything bagel with lox & morning latte at Forage; the East Promenade for a food truck lunch, then a stroll along the waterfront trail to the port area for an ice cream cone at Gorgeous gelato; afternoon coffee at Double Great Coffee; and a post-dinner whiskey @ Independence Ice. Only downside on my visit was the upstairs neighbor. Dude clearly isn't a principal dancer in the Portland Ballet, as light on his feet wouldn't describe him. Not a stereo or TV issue - you can just hear the noise from him walking (8AM-10PM when there)

This was a perfect location for enjoying being in the heart of Old Orchard Beach. You get live music down stairs, a few steps away from the beach, quick walk to downtown/pier. Totally worth it! The condo is beautiful and comfortable.

The place was very easy to find, great location. Walking distance along the beach and sidewalk to attractions, great access to the beach. Very clean and well maintained place. The hosts are very responsive and polite with good recommendations of places to eat and things to do. Would definitely stay again!

I would recommend it 100%

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Great place to stay. Beautiful scenery, very quiet exactly as advertised.

This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.

My stay here was wonderful! The perfect homebase for our trip. Everything was exactly as described and then some. A great sea breeze and a cozy space to rest and relax before hitting the beach or walking into town. I felt right at home. I can't wait to go back again! 💜