We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chebeague Island Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
50 rentals in Chebeague Island.
Sort by:
Tripadvisor Sort
Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!, holiday rental in Chebeague Island

Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stunning views and comfort complete your ultimate Maine island vacation getaway., holiday rental in Chebeague Island

Stunning views and comfort complete your ultimate Maine island vacation getaway.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay, holiday rental in Chebeague Island

Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, holiday rental in Chebeague Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views!, holiday rental in Chebeague Island

Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!, holiday rental in Chebeague Island

Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ocean View Cottage Falmouth Foreside, holiday rental in Chebeague Island

Ocean View Cottage Falmouth Foreside

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Falmouth Furnished 3 Bedroom 2 Bath Loft Close to Portland, holiday rental in Chebeague Island

Beautiful Falmouth Furnished 3 Bedroom 2 Bath Loft Close to Portland

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Quaint Guest Cottage Overlooking Potts Harbor, holiday rental in Chebeague Island

Quaint Guest Cottage Overlooking Potts Harbor

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
New Well Built Elegant Home on the Water 2 miles to Freeport, 9  to Portland!, holiday rental in Chebeague Island

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Chebeague Island rentals sent straight to your email!
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room, holiday rental in Chebeague Island

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Brand new, year-round oceanfront home at the tip of Potts Pt. Private beach., holiday rental in Chebeague Island

Brand new, year-round oceanfront home at the tip of Potts Pt. Private beach.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ocean Breezes 2br Freeport, Maine Apartment, holiday rental in Chebeague Island

Ocean Breezes 2br Freeport, Maine Apartment

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEW LISTING ☼ Unique Oceanfront Home, holiday rental in Chebeague Island

NEW LISTING ☼ Unique Oceanfront Home

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home, holiday rental in Chebeague Island

PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming Freshly Updated 1BR/1BA Villa with great location close to town & beach, holiday rental in Chebeague Island

Charming Freshly Updated 1BR/1BA Villa with great location close to town & beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Falmouth Waterfront Carriage House Apt, holiday rental in Chebeague Island

Falmouth Waterfront Carriage House Apt

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Family & Pet Friendly Log House On Casco Bay, holiday rental in Chebeague Island

Family & Pet Friendly Log House On Casco Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Adorable cottage with million dollar view and short walk to stunning beach., holiday rental in Chebeague Island

Adorable cottage with million dollar view and short walk to stunning beach.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautifully decorated executive home steps from a private beach, holiday rental in Chebeague Island

Beautifully decorated executive home steps from a private beach

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spectacular Views, Peaceful & Private, holiday rental in Chebeague Island

Spectacular Views, Peaceful & Private

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
HARPSWELL MAINE - The Cottage * AshPoint, holiday rental in Chebeague Island

HARPSWELL MAINE - The Cottage * AshPoint

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
A cottage with a view and so much more!, holiday rental in Chebeague Island

A cottage with a view and so much more!

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Adorable Peaks Island Cottage, holiday rental in Chebeague Island

Adorable Peaks Island Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stover's Cove Beach Coastal Retreat, holiday rental in Chebeague Island

Stover's Cove Beach Coastal Retreat

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Evergreen cottage 5' from the water, holiday rental in Chebeague Island

Evergreen cottage 5' from the water

5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
DIRECT OCEANFRONT Perfect location, holiday rental in Chebeague Island

DIRECT OCEANFRONT Perfect location

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Historic Island Cottage, 5BR, holiday rental in Chebeague Island

Historic Island Cottage, 5BR

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Updated waterfront cottage w/private deck, gas grill & dock access, holiday rental in Chebeague Island

Updated waterfront cottage w/private deck, gas grill & dock access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Island Escape - Spacious 4 BR House with Car included!, holiday rental in Chebeague Island

Island Escape - Spacious 4 BR House with Car included!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Sunset Cottage, Family-Friendly Oasis, holiday rental in Chebeague Island

Sunset Cottage, Family-Friendly Oasis

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ocean Front Cottage, Harpswell, ME, holiday rental in Chebeague Island

Ocean Front Cottage, Harpswell, ME

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A charming, seaside cottage ~ Falmouth Foreside, holiday rental in Chebeague Island

A charming, seaside cottage ~ Falmouth Foreside

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Oceanfront cottage with stunning sunrises over the Cribstone Bridge, holiday rental in Chebeague Island

Oceanfront cottage with stunning sunrises over the Cribstone Bridge

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mackerel Cove, Bailey Island. Brand New Fully Equipped Luxury Home. Sleeps 8, holiday rental in Chebeague Island

Mackerel Cove, Bailey Island. Brand New Fully Equipped Luxury Home. Sleeps 8

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Authentic Coastal Maine Cottage Living, holiday rental in Chebeague Island

Authentic Coastal Maine Cottage Living

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Classic Maine Cottage with astonishing easterly views located walking distance t, holiday rental in Chebeague Island

Classic Maine Cottage with astonishing easterly views located walking distance t

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
New listing! Waterfront home w/ a furnished deck, ocean views, & a full kitchen, holiday rental in Chebeague Island

New listing! Waterfront home w/ a furnished deck, ocean views, & a full kitchen

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Historic cottage with views of Mackerel Cove and right of way to Little Harbor!, holiday rental in Chebeague Island

Historic cottage with views of Mackerel Cove and right of way to Little Harbor!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private Oceanfront Island Estate - Sleeps up to 22!, holiday rental in Chebeague Island

Private Oceanfront Island Estate - Sleeps up to 22!

3 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming cottage on Basin Cove just a short drive to the Dolphin Marina, holiday rental in Chebeague Island

Charming cottage on Basin Cove just a short drive to the Dolphin Marina

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Classic Maine Beach Cottage, private beach access, holiday rental in Chebeague Island

Classic Maine Beach Cottage, private beach access

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
'Heron Cottage' on Casco Bay w/Deck & Dock Access!, holiday rental in Chebeague Island

'Heron Cottage' on Casco Bay w/Deck & Dock Access!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Seaside Island Home, holiday rental in Chebeague Island

Beautiful Seaside Island Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Grace Cottage, holiday rental in Chebeague Island

Grace Cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Freeport Hideaway w/ 2 Decks & Water View, holiday rental in Chebeague Island

Spacious Freeport Hideaway w/ 2 Decks & Water View

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Iconic Town Landing Market Guesthouse, holiday rental in Chebeague Island

The Iconic Town Landing Market Guesthouse

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Chebeague Island

Luxury Coastal Home w2 Living Rooms, Pool, Rooftop

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Chebeague Island

Luxury Coastal Home w2 Living Rooms, Pool, Rooftop

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEW! Serene Freeport Cottage on Harraseeket River!, holiday rental in Chebeague Island

NEW! Serene Freeport Cottage on Harraseeket River!

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Chebeague Island