Chebeague Island Vacation Rentals
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Vacation Rentals in Chebeague Island
Sunny Modern Oasis in Portland’s Trendy East End
Portland ME
A stay at this vacation home places you in the heart of Portland, steps from Casco Bay and 4 minutes by foot from Portland Observatory.
Kitchen
Washer
Fantastic Waterfront Views
Phippsburg ME
$350 nightly
The price is $373 total per night
$373 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Kitchen
Washer
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
Old Orchard Beach ME
$1,256 nightly
The price is $1,369 total per night
$1,369 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
With a stay at this vacation home in Old Orchard Beach, you'll be by the sea, within a 10-minute drive of Engine and Old Orchard Beach.
Hot Tub
Kitchen
Captain's Guest Room w/private bath. Walk to everything.
Bath ME
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Pet friendly
Free WiFi
Large, light filled 4 bedroom house - walk to ocean and ferry
Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 6 minutes by foot from Richard Boyd Art Gallery.
Kitchen
Washer
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
Old Orchard Beach ME
With a stay at this vacation home in Old Orchard Beach, you'll be on the beach, within a 10-minute drive of Engine and Old Orchard Beach.
Kitchen
Washer
Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub
Old Orchard Beach ME
With a stay at this vacation home, you'll be centrally located in Old Orchard Beach, within a 10-minute drive of Engine and Harmon Historical Museum.
Hot Tub
Kitchen
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Old Orchard Beach ME
$439 nightly
The price is $478 total per night
$478 total
Dec 11 - Dec 12
Total with taxes and fees
With a stay at this vacation home in Old Orchard Beach, you'll be within a 10-minute drive of Engine and Harmon Historical Museum.
Kitchen
Washer
Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock
Woolwich ME
Located in Woolwich, this vacation home is within a 5-minute drive of Kennebec River and Markings Gallery.
Kitchen
Washer
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Harpswell ME
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 4-minute drive from Mitchell Field.
Kitchen
Washer
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View all propertiesLowest 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.
Chebeague Island Vacation Rentals essential information
Accommodation | 600 Vacation Rentals |
|---|---|
Lowest Price | $373 |
Highest Price | $1,369 |
Popular accommodation | Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!, Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, The Perfect Beach Escape: Cozy 4-Bedroom Retreat, Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub, The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi, Lone Pine Cottage Maine - Chef’s Kitchen |