Holiday rentals with outdoor seating in Chebeague Island

a wonderful place to stay.

Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10

Great spot for a private getaway! Hosts were very friendly, flexible and ensured we had everything we needed. Would absolutely visit again and recommend 100%

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

Stop scrolling & just book this amazing home! Randy is an excellent, gracious & very responsive host! Check-in was a breeze w/ wonderful detailed instructions for the house and region sent in advance. This house is awesome, pristine clean, beautifully decorated and outfitted. Totally turnkey set up as they thought of everything one might need to cook, relax, sleep, explore and enjoy your visit! It's very evident that these hosts want their guests to have an exceptional experience and we did! Beds were comfy along with plenty of high quality linens and supplies. We truly cannot wait to return on what will be our regular road trips to Maine! We toured Boothbay, Chebeague Island, Brunswick, Portland, Kennebunkport, Freeport and Ogunquit while we were there. Yarmouth is awesome with super friendly locals! Close by, we found Rosemont Market, Maggie Mae's Cafe and Royal River Grille convenient options among many good ones in the area. Thanks to our host for the wine & chocolate!

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

Rhonda’s house was so charming with its many decorations from the 1940s, 1950s. It felt very cozy and completely comfortable there for the five of us. The grands loved the loft with the toys, and we adults appreciated the awesome shower and towel filled bathroom. So nice! Very comfortable beds, well equipped kitchen, easy to get into entrance, porch a nice place to relax. Great AC, too. Beautifully clean and tidy. Very close to downtown Portland for all of the going’s on and super restaurants. We would definitely stay again.

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.

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!

Cozy place in a nice area! Walkable to downtown. Great communication - very nice and accommodating! We had a great trip :-)

Great little place. We parked our car and trailer right in front of the house, had takeout and a few groceries delivered (I think we used DoorDash or GrubHub), and got rested up for the next leg of our trip. Hyeri was super kind and responsive.

Arian’s house is so lovely. It’s cozy, modern and very clean. The house is in an excellent location close to restaurants and walking paths. Arian was responsive and helpful. We highly recommend his place if you’re looking for somewhere to stay in Portland

Great location just a short drive into downtown. Also, we really enjoyed the local restaurants, ice cream stand, and coffee shop all within a few blocks of the place. The beds and coach are very comfortable, we would consider staying again upon our return. As other comments have mentioned, there is resident family above which I believe includes a younger child who can be heard running around a lot. This is an older building so I am guessing hardwood floors are throughout and that accentuated the noise.

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!

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!

Dax was a very friendly, accommodating host. The place was very cute and also very clean upon arrival. We would definitely book again!

Great stay

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

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!

We had a great stay at Tysons place. Its a perfect location, only like 5-10 minutes drive from Old Port. The home is clean and beautiful. Street parking was super easy. Always space right on the side of the home. Each room has its own A/C. Would definitely recommend staying at Tysons place!

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.

Great place! Close to the beach. Easy and fast communication when we needed to specify parking questions.

You cannot beat the location with this rental. We love coming to Willard Beach with our pup, and when our old go-to BNB stopped renting we were so worried we wouldn’t find another. But this condo worked out so perfectly in terms of location (across the road from both Scratch Bakery and Willard Scoops, comfortable walk to the beach with several entrance options) and the actual comfort of the condo itself. The proximity to the beach was really a plus for us, as we didn’t have to get up as early to make the dog friendly beach hours! Host is responsive, and any household items (eg. soap, coffee filters) that were missing from the condo we could easily run down to get from Hannaford. The downsides: It is on a second floor walk up, which may be challenging for those with mobility issues. Hand railing is odd too. Bit pricey, couldn’t swing a full week this time around as the price shot up dramatically when I added Friday to the duration. But overall, really lovely!

Great place to stay, Ogunquit is such an endearing place to be 😄