Chebeague Island Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chebeague Island vacation rentals

Escape to Positive Outlook
Escape to Positive OutlookWest Point
10.0 out of 10, Exceptional, (3)
The price is ¥13,116
¥29,581 total
includes taxes & fees
Jan 4 - Jan 5, 2026

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Large suite/private bath/private entrance on quiet street near Thomas Pt. BeachBrunswick
10.0 out of 10, Exceptional, (145)
The price is ¥14,035
¥18,698 total
includes taxes & fees
Dec 30 - Dec 31

Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!
Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!Bath
8.6 out of 10, Excellent, (10)
The price is ¥21,782
¥27,147 total
includes taxes & fees
Dec 28 - Dec 29

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick Downtown Sugar Cube next to BowdoinBrunswick
8.4 out of 10, Very Good, (7)
The price is ¥14,814
¥41,134 total
includes taxes & fees
Jan 1 - Jan 2, 2026

Modern style in historic building in downtown Bath
Modern style in historic building in downtown BathBath
10.0 out of 10, Exceptional, (8)
The price is ¥15,594
¥34,505 total
includes taxes & fees
Jan 25 - Jan 26, 2026

Pine Point Beach private, quaint, charming studio.
Pine Point Beach private, quaint, charming studio.Blue Point
10.0 out of 10, Exceptional, (24)
The price is ¥12,475
¥31,105 total
includes taxes & fees
Dec 28 - Dec 29

9.8 out of 10, Exceptional, (24)
The price is ¥15,126
¥31,445 total
includes taxes & fees
Jan 12 - Jan 13, 2026

Modern, Luxurious, Cabin in the Woods - 17
Modern, Luxurious, Cabin in the Woods - 17Freeport
10.0 out of 10, Exceptional, (3)
The price is ¥33,102
¥54,632 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Chebeague Island Hotel Reviews

Canopy by Hilton Portland Waterfront
10/10 Excellent
Find out more about Chebeague Island
Search for holiday rentals in Chebeague Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Chebeague Island using one of the methods below:
- View our selection of featured holiday rentals in Chebeague Island
- Use the map to find apartments and other holiday homes in the Chebeague Island neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Chebeague Island while they last
Look no further and take a look at our great range of rental properties in Chebeague Island!

















































































