
Vacation rentals in Chebeague Island
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Top-rated vacation rentals in Chebeague Island
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Chebeague Island vacation rentals
Other great vacation rentals in Chebeague Island
Guest favourite

Home in Scarborough
4.93 out of 5 average rating, 58 reviewsGorgeous 4 BR home with HOT TUB
Elizabeth AnnRating, 5 stars1 week ago
The home was beautiful and matched the photos online. Clean and inviting! Gregory was responsive while booking and during our stay. Very kind and would stay here again for another girls weekend get away!
Superhost

Home in Newcastle
4.91 out of 5 average rating, 32 reviewsSpring 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 reviewscozy 3 bedroom ranch with deck and screen porch
MichaelRating, 5 stars3 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.
Top guest favourite

Home in Bath
5 out of 5 average rating, 101 reviewsWaterfront Farmhouse with Modern Flair!
Tony & KellyRating, 5 stars1 month 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 Freedom
4.9 out of 5 average rating, 94 reviewsOur Mountain Retreat – Lake Ossipee Access
FinRating, 5 stars1 month ago
Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!
Top guest favourite

Apartment in Old Orchard Beach
5 out of 5 average rating, 50 reviewsHorizon View Hideaway with Deck
ReneeRating, 5 stars6 months ago
The house is beautiful and very comfortable. We had everything we needed. The host was very friendly and responsive. We would definitely stay there again.
Guest favourite

Home in Old Orchard Beach
4.83 out of 5 average rating, 30 reviewsBeautiful Spacious OOB Beachfront home w/ elevator
KimberlyRating, 5 stars3 months ago
This place is absolutely amazing. Right on the beach, facing the water, with amazing ocean views from almost every spot in the house. The open concept kitchen/dining/living space was perfect for family time. The bedrooms were spacious and comfortable. The master suite is a dream - wake up to the waves, soak in the large jet tub, enjoy a large walk-in closet. Quality linens and towels throughout. Well stocked kitchen. The bar and pool table area provided fun entertainment. This was a wonderful getaway in luxury. The elevator was not working while we were there, but was due to be repaired within the week. The host communicated throughout the stay, offering local recommendations and checking in to be sure everything was ok with our stay. Would be a perfect place for a family event as well. Highly recommend!
Top guest favourite

Home in Greenwood
4.93 out of 5 average rating, 76 reviewsThe Farmhouse at The Cross Farm
CordeliaRating, 5 stars3 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 vacation rentals in Chebeague Island
Total rentals
180 properties
Nightly prices starting at
$83 CAD 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
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- Wells Beach
- Ogunquit Playhouse
- East End Beach
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Purity Spring Resort
- King Pine Ski Area
- Popham Beach State Park
- Parsons Beach
- Laudholm Beach
- Funtown Splashtown USA
- Mothers Beach
- Palace Playland
- Cliff House Beach
- Ferry Beach
- West Shore Sandy Beach
- Portland Museum of Art
- Crescent Beach State Park
- Pemaquid Beach
- PowderHouse Hill
- Western Beach