Family-friendly vacation rentals in Chebeague Island

10/10 would recommend - Mary Alice’s place is comfortable & cozy. Very well equipped for a getaway to beautiful Kittery! She’s also a wonderful and helpful host.

Meghan's home was a perfect place to stay for my sister's Bachelorette weekend! The home is located in a quiet community with views of the river and bay, and it was conveniently located with just a short drive into the heart of Portland. We found our stay extremely comfortable, especially on such a cold and dreary April weekend. Meghan had the hottub ready for us with matching robes for all which was a fun surprise. Check in and check out were a breeze. We even took a breakfast recommendation from the guest book (Forage Market, yum!), a tasty experience indeed. Thanks again, Meghan!

We love staying at the Brownie. It’s a great home for any active family that appreciates a quiet surrounding. Great home and so close to SR. It can’t be beat.

We spent a lovely few days at this property enjoying the winter weather at its finest. The house is close to everything but still felt private and cozy. A great choice for families!

Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

We just had a wonderful ladie's weekend at Christy's place! We lucked out and got a bit of snow, so the cabin was the perfect cozy spot to spend the weekend with a fire and a puzzle! The hot tub was an extra added bonus! Beds were all very comfortable and living room was super cozy. Very easy ride to downtown for restaurants and shopping for a bit. Would definitely recommend!

We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

Was a very nice peaceful getaway the home was spotless and had everything we needed plus extra great place to disconnect

We had a great weekend with a blended family of young adults! There was hiking and visiting family also visiting while there! Great space and location!

Scott's place was perfect for our small family's ski trip! It was exactly as pictured, had everything we needed for our stay, and was so close to Sunday River (~10 minutes) and right down the road from restaurants in Bethel Village. We would love to stay again on our next ski trip!

Perfect stay for 4 adults, 1 infant, and 1 dog! Love the two-bedroom, two-bathroom layout, plus the kitchenette to make oatmeal and toast in the morning before hitting the ski trails. Clear check-in instructions, no hassle at all even when we arrived around midnight.

I booked the house as a place for my family of 6 (4 adult children) and our black lab, to come together for Easter weekend. Since my boys live in Portsmouth we only needed 2 bedrooms and this house made the perfect getaway and place to host dinners. The house was spacious and very comfortable. We enjoyed the enormous fenced in yard all weekend. The host had many yard games which we played and our lab was so happy too. The fire pit was an added bonus for a night of s’more making. We truly had a wonderful time and the house really felt like home. Ps the stairs are fine once you get used to them. Rebecca was responsive and a wonderful host.

Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

We had a wonderful girl's trip staying in Diana's house! We walked to the beach and to Scratch bakery (twice). The house was perfect for the five of us with a great sitting area to hang out and chat. The house was clean and the instructions for cleaning up were easy to follow.

We loved our stay at Katie's house in Portland. It was very comfortable, clean and nicely decorated. We would love to stay again soon!

A group of 5 of us stayed at Kathy's listing and felt like we had plenty of room. We were all comfortable and found the location to be great with plenty to do within walking distance. Some of the doors were glass with blinds/shades that weren't entirely opaque so we had to be somewhat mindful when changing in our room. The front door battery was dead when we arrived and so the door was unlocked but this was quickly resolved with the help of the host and extra batteries on site. Location was fabulous and peaceful. No issues with finding free street parking, either. Overall, we enjoyed our time here and would stay at this listing again!

We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

This may not be the most picturesque airbnb you've laid eyes on, but it was HANDS DOWN the best accommodation I have EVER stayed in with my toddlers (we have been on 10 trips in the last 3 years!) Dan's place was cozy and the right amount of space for my family of four, but the thing that made it really stand out is that they had everything you could need for young kids. Not only the standard pack and play and highchair, but also a sound machine, stroller, and best of all- a box of toys that my two (4 and 1.5) played with CONSTANTLY every spare moment we were in the airbnb. We stayed a week and they didn't get bored of them, which, if you've ever had two energetic kids running circles around the living room, you know REALLY says something. The kitchen had everything we could possibly need as well, which was so helpful. This place is priced fantastically for families and I would whole heartedly recommend it.

The condo was nicely stocked and had everything we needed for our family. Extra blankets in each closet and the beds were so comfortable! Easy to find and very close to the mountain we were skiing at for the week. Clubhouse with the pool was also within walking distance which was a huge plus.

Had a wonderful stay at Christophers place. He is a great host, always responsive with clear instructions. Place was peaceful, private and is exactly same as it was in the pictures. Will come soon!

We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

This was our 2nd time staying at Staci’s place — it is one of our favorite rentals (and we travel a lot!)!! The location is perfect and Staci is super responsive. The home itself is cozy, clean and well-equipped with the essentials plus games. Our family of 4 enjoyed the pool and hot tub, as well as puzzling at the dining room table with the fire going :)

Michelle and Jason's place was very comfortable, clean and cozy. There was a variety of pots, pans and utensils which allowed us to cook whatever we wanted. There were other people staying in the unit, but it was very quiet. A great find for a long weekend of hiking!

We had a wonderful stay! The house was spacious and perfect for our large group of friends (three families). The kitchen was well-stocked, and the large dining table made for a memorable Christmas dinner together. The location was fantastic—just a 10-minute drive to the waterpark and Attitash Mountain, and about an hour to Santa’s Village and several other ski resorts. There were also multiple grocery stores conveniently nearby. Overall, the house had everything we needed for a comfortable and enjoyable trip. Highly recommend!