Lodging Image

Chebeague Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chebeague Island vacation rentals

Interior

'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is P24,230
P37,667 total
includes taxes & fees
Jul 19 - Jul 20
'osprey Cottage' South Freeport Home on Casco Bay!
Private kitchen

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (101 reviews)
"Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"
United States
Roberta
The price is P21,096
P27,595 total
includes taxes & fees
Jul 8 - Jul 9
The Weldon Hotel
Private kitchen

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
3.5 star property
Gray
The price is P29,242
P83,241 total
includes taxes & fees
Jul 2 - Jul 3
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
Egyptian cotton sheets, premium bedding, down comforters, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is P25,240
P27,512 total
includes taxes & fees
Jul 2 - Jul 3
Fortland Island Campground
Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is P8,281
P18,842 total
includes taxes & fees
Jul 16 - Jul 17
1 Mi to Maine Street! Mcm-style Home in Brunswick
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Grand Beach Inn

Grand Beach Inn

10/10 Excellent
"My room was clean and staff was friendly. It’s a decent place to stay and right across the street from the beach. There is a heated pool and it is very family friendly."
Marilyn 2-night trip
Posted 2 hours ago
Grand Beach Inn

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!

Frequently asked questions

Are there vacation rentals in Chebeague Island?

Yes, we have vacation rentals near popular attractions in Chebeague Island, or you can select a secluded option if you're looking for relaxation. Chebeague Island is known for its shopping and restaurants.

How many vacation rentals are there in Chebeague Island?

Expedia has 4 vacation rentals for your stay in Chebeague Island.

What can I see and do in Chebeague Island?

Explore the area and family-friendly sights such as Portland Observatory, or get out into nature at a spot like Wolfe's Neck Farm. Wolfe's Neck Woods State Park and Bailey Island Bridge are a couple of places you'll find in the larger area.

What are vacation rentals like in Chebeague Island?

Vacation rentals are private properties you can book for several days or more in Chebeague Island. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a small group gathering.