House holiday rentals in Chebeague Island

Great backyard with a pool, hot tub, fire pit and privacy with the woods.

This was the perfect home base for exploring various parts of the Maine coast. Beds were comfy, and each room had a wall unit to make it the temperature you like. Our kids loved being upstairs in the 3 beds room and having their own space. WiFi worked great, and that was with 7 of us on it doing various things - adults working, kids streaming. Would definitely stay here again.

We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

Gorgeous house, peaceful area, a great back deck with pool and hot tub! Jey was a great host, very helpful and quick response time. The house was very clean and put together. I would totally recommend staying at jeys house!!

Had a quick weekend getaway at Keith's place. Everything was perfect. Easy check in and great communication.

We had a wonderful stay in Angela’s beautiful home. It had great amenities, was super clean, and had everything we needed. Loved the pool and fire pit. The kitchen was roomy for cooking too. 5 stars!

Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Beautiful home in a quiet, family-friendly community. We loved being able to walk up to the pool and play in the game room in the main clubhouse area. The house is a short drive to downtown Kennebunkport and local beaches. It is a quick 30 minute drive up to Portland. Our daughter loved sleeping in the private bedroom upstairs. The kitchen was fully stocked with appliances. The space was immaculate when we arrived. Steve was responsive to any needs we had during our stay. A great find!

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!

Central location, but was surprisingly very quiet and private. Kelsey is an excellent communicator and host.

Sheri's place was comfortable, clean, and in a beautiful location.

We can’t say enough good things about this stay. We came for our honeymoon, and were met with flowers and a few other treats from the host as a gift. How sweet! As far as the property, the cottage is perfectly sized for two or three, and is designed delightfully. It is on a shared lot with the family’s primary residence , but feels very comfortable and private. A close by walk to the water as well. Inside, you will find everything you could ever need from pots and pans, spices, towels, and the best recommendations for the area. We’d build our own version of this cottage to take home with us if we could. We hope to one day be back and will always remember our amazing time in Harpswell.

Kevin's place worked really well for my two dogs and myself. There is a fenced in back yard. I liked the setup of the primary bedroom with the attached full bath and laundry. Comfortable bed! Very quiet neighborhood and very convenient to access other areas of Portland. I really appreciated the back deck setup. I need to find the comfy chair they have out back for my own home! Clean and usable kitchen. Nice stack of Maine materials and recommendations for local items to check out. Overall, a very pleasant stay, thank you!

Our stay at Laurel Shore Cottage was just what we needed. The location was serene - and we spent most afternoons and evenings sitting on the porch soaking in the beautiful landscape and scenery. The cottage itself was uncluttered and comfortable and the host was very responsive.

What a beautiful spot for a lovely weekend with friends. We enjoyed the contrast of exploring Portland, with the 15 min. escape back to this peaceful and beautiful home. This spot has everything you need, is comfortable for a group, and allows you to soak up the natural surroundings and space without being too much of a car ride away from the amazing city that is Portland. Would definitely stay again or even move in if I could :)

Alina was a great host and the place is beautiful and had everything we needed and was exactly as described.

Fantastic stay! Comfortable, peaceful and amazing location. Lots of space we felt right at home and our dog loved going for walks in the yard. We look forward to staying again!

Would definitely stay here again. Was really a first class space that made our family feel very relaxed.

What a fantastic place! Great amenities for a luxurious stay at the house, all the tools you may need if you wanted to cook at home, and so conveniently located to Old Port if you want some great food and drinks in the city. We stayed for 3 nights with another couple. We spent time in Old port visiting restaurants and a few breweries/distilleries and ended the nights by the firepit in the back yard. Took a nice walk. We also made a nice dinner after grabbing some great produce at the Protland Farmaers market. Wish we had more time!

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!

Such a lovely, cozy spot! We stayed for two nights with toddlers and our dog and everyone was very happy there.

Kate’s place is in a beautiful location and has so much to do. We loved the wildlife, the easy access to Portland and all the yard games. We can’t wait to come back!

Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!

Cape Elizebeth is very beautiful even in the early winter! I got to see the sunshine, snow and rain all in a cozy home! I highly recommend This home! It is stocked with everything you would need, even puzzles, of which I am a fan!