Holiday rentals with outdoor seating in Chebeague Island

I had a wonderful stay at Cutter House! The beautiful grounds, with the charming red barn and friendly animals, created such a peaceful and inviting atmosphere. One of the highlights was the visits from the friendly, snuggly Great Pyrenees dog—such a gentle and affectionate companion who made the experience even more special. I loved spending time outdoors exploring the yard. The home itself is warm, cozy, and thoughtfully appointed. With two bedrooms and two full bathrooms, it was comfortable and convenient. The kitchen was well-stocked, and the fresh local coffee beans made my mornings extra special. The host Maria, was welcoming and communicative, providing helpful local tips and making sure I had everything I needed. Cutter House is the perfect retreat for anyone looking to relax in a beautiful, cozy setting with a touch of furry warmth. I look forward to returning! Don't forget to ask about Grace! She holds a record in Maine!!

We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

Natasha’s house was perfect for our family vacation in Maine. The house is charming and had everything we needed and then some - appreciated all the kids toys and crib! The views are absolutely incredible. Would recommend!

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

This is such a beautiful space! Very cozy and tucked away in a residential area. The home felt safe and was very close to downtown Freeport, where there are great options for food/beverage and shopping.

We had a great stay. The location was perfect for accessing a number of great locations, Peter was friendly and helpful, and we felt the AirBnB was equipped with everything we could have needed.

We had a wonderful stay! The house was impeccable with an incredible view of the ocean. We had everything we could want. Marsha was a wonderful host and we’re so glad we stayed here!

We had a fantastic stay at Sari and Saul’s place! Traveling with an infant and a 7-year-old can be a lot, but their home had everything we needed to keep both kids happy and entertained. It was cozy, well-stocked, and surrounded by beautiful nature — a perfect family escape. We’ll definitely be back and wouldn’t hesitate to recommend it to friends!

Great location close to downtown Portland. Lots of walkable places close by for coffee and breakfast. A little farther to some unique restaurants. We Uber'd a lot which worked out great to avoid parking around Portland. We would definitely secure this nice place the next time we come to Portland!

My boyfriend and I had a lovely stay. We enjoyed drinking coffee out on the patio in the mornings and cooking meals in the kitchen. The place was clean and just what we needed for the week. Victoria and Tanner were also very friendly and quick to reply to our messages. We would come back!

We needed a place for my son’s externship. Setup for a long stay and feel like home. All the amenities made for an easy tradition to have everything provided and setup beyond expectations. Super quick and kind with any questions and concerns. Would highly recommend anyone to stay at this listing. A east walk to downtown and any site seeing.

We had a great stay. The location is quiet but just a few minutes away from amazing restaurants, cafes, and breweries. Highlights: The bed was super comfortable. The sauna was great on a rainy day. The walkability to the Back Bay trail was appreciated.

Great location that is nearby for runs/walks and quick driving commutes to downtown and other hot spots. The space was cozy and clean.

Great stay! Location is perfect for everything we wanted to do, be by the water, stay right next to downtown, and a short walk from our tour with Eco Adventures. Furniture was very comfortable and everything was clean. Great restaurants in the area. Would return back!

This was our second stay with Emily in less than a month. Just as comfortable and convenient as the first time. We hope to book her space again for the holidays this year.

A perfect stay. The accommodation is superbly located and you can easily explore Portland on foot. There are many restaurants, etc. nearby, the selection is great. Sharon and Eric were perfect hosts and we felt completely comfortable. The accommodation is very clean and has everything you need. The private parking space is also a big plus. Thank you Sharon & Eric for a great stay and for making us feel at home. We will be back!

Great stay

Very nice stay! The location is perfect, everything you need is on site. I recommend it!

We had a great time! The place was very clean, nicely maintained, and in a perfect location—just a short drive to local coffee shops and great restaurants. The surrounding nature was absolutely beautiful and made the whole trip feel relaxing and refreshing. Highly recommend!

Wonderful little spot very close to the beach. Plenty of places to walk to from the location as well as a short drive to Old Orchard Beach. Would come back in a heartbeat!

Great place to stay if you want to be close to downtown but with a larger, comfortable space. The place is exactly as described, exceptionally clean and tastefully decorated. No dollar store products here! The ground coffee and half and half really made it feel like we were staying at a friend’s home.

We had a great time! The condo is clean, cozy, and comfortable. I highly recommend this AirBnB, especially for the beach proximity.

We loved our stay! The space is beautiful and cozy. The walk to the family friendly beach was just the right distance for my 4yo. The neighborhood is adorable and friendly! With an amazing bakery and ice cream shop just around the corner! Dave was a great host and took great care of us.

We’ve stayed here 3x so far and will always come back. This place is such a unique stay with live music right below. You can open the balcony doors and see and hear the ocean. The home is always clean and feels very homey. We truly love it here and will always choose to stay at this airbnb.