Holiday houses in Chebeague Island

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Popular amenities for Chebeague Island holiday rentals

Stay near Chebeague Island's top sights

Chebeague Island Inn12 locals recommend
Littlejohn Island Preserve7 locals recommend
Slow Bell Cafe5 locals recommend
Doughty's Island Market4 locals recommend
Great Chebeague Golf Club3 locals recommend
The Niblic & Gallery3 locals recommend

Other great holiday rentals in Chebeague Island

Guest favourite
Home in Scarborough
4.93 out of 5 average rating, 59 reviews

Gorgeous 4 BR home with HOT TUB

ShellyRating, 5 stars1 week ago
Gregory's place was great for our 2 night getaway. Hot tub was amazing and private from neighbors. Bathrooms and kitchens were well stocked. I will definitely go back for another getaway
Superhost
Home in Newcastle
4.91 out of 5 average rating, 32 reviews

Spring into the season eating lobsters w/friends

MarceloRating, 5 stars7 months ago
Very nice place to stay big nice and clean recommended this place to everyone looking for a good place big and clean this the right place
Top Guest favourite
Home in Gray
4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.
Guest favourite
Home in Kennebunk
4.95 out of 5 average rating, 151 reviews

Quiet cozy cottage close to restaurants, beach

MikeRating, 5 stars6 months ago
Lori’s place was very cozy and a great screened in back porch. Perfect for morning coffee while taking in the scenery. Easily walkable to downtown and restaurants and right down the street from the beach. Nicely located for all things. We rented a car on our stay and travelled to Portland, Portsmouth NH and then close by towns to Kennebunk. All under an hours drive. We enjoyed our stay at Lori’s place.
Top Guest favourite
Home in Bath
5 out of 5 average rating, 101 reviews

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars2 months ago
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.
Guest favourite
Home in Old Orchard Beach
4.84 out of 5 average rating, 31 reviews

Beautiful Spacious OOB Beachfront home w/ elevator

AnaRating, 5 stars1 week ago
We went off season and it was a very beautiful and tranquil beach experience. The house is gorgeous and spacious. Jason was very responsive and friendly. We will definitely be back!
Guest favourite
Cabin in West Paris
4.94 out of 5 average rating, 108 reviews

Cabin on the hill!

AmandaRating, 5 stars2 weeks ago
This was a fantastic find in a private and quiet area. The hot tub and sauna were fantastic as it snowed a bit while we were there. It’s a great space with a rustic feel and fun vibe. As someone that lives in Maine and enjoys finding places like this, we will definitely be back.
Top Guest favourite
Home in Greenwood
4.93 out of 5 average rating, 76 reviews

The Farmhouse at The Cross Farm

CordeliaRating, 5 stars4 months ago
Amazing view with lots to do, spacious house, well stocked, good location for skiing, peaceful and quiet. Host is very friendly, responsive and helpful. He delighted us with delicious chocolate and fresh cookies. Thanks Tony! Highly recommended!

Quick stats about holiday rentals in Chebeague Island

  • Total rentals

    180 properties

  • Nightly prices starting at

    $94 AUD before taxes and fees

  • Total number of reviews

    4.2K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore