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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chebeague Island holiday rentals

Front of property

1. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is RM2,228
RM3,042 total
includes taxes & fees
31 Aug - 1 Sept
Evalina Hotel
Private kitchen

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (110 reviews)
"Really nice room and location"
United States
Victoria
The price is RM1,203
RM1,618 total
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel
Egyptian cotton sheets, premium bedding, down duvets, bed sheets

3. 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 RM1,387
RM2,180 total
includes taxes & fees
7 Sept - 8 Sept
Fortland Island Campground
Front of property

4. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is RM515
RM1,379 total
includes taxes & fees
26 Aug - 27 Aug
1/2 Mi to Pier: Wfh-friendly Apt in Maine!
Private kitchen

5. 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 RM2,653
RM5,597 total
includes taxes & fees
8 Sept - 9 Sept
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
Interior

6. Steps to Sandy Beach! Oceanfront Old Orchard Gem

Steps to Sandy Beach! Oceanfront Old Orchard Gem
3.0 star property
Old Orchard Beach
The price is RM858
RM1,507 total
includes taxes & fees
24 Aug - 25 Aug
Steps to Sandy Beach! Oceanfront Old Orchard Gem
Front of property

7. 'beachfront 14' Condo on Old Orchard Beach

'beachfront 14' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is RM911
RM1,511 total
includes taxes & fees
23 Aug - 24 Aug
'beachfront 14' Condo on Old Orchard Beach
Interior

8. 1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach

1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is RM588
RM1,459 total
includes taxes & fees
19 Aug - 20 Aug
1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach
Interior

9. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is RM466
RM1,325 total
includes taxes & fees
25 Aug - 26 Aug
Walk to Pier & Ocean: Apt in Old Orchard Beach!
Front of property

10. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is RM588
RM1,159 total
includes taxes & fees
14 Sept - 15 Sept
'beachfront 9' Condo on Old Orchard Beach
Interior

11. 'beachfront 12' Condo on Old Orchard Beach

'beachfront 12' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is RM1,009
RM1,618 total
includes taxes & fees
8 Sept - 9 Sept
'beachfront 12' Condo on Old Orchard Beach
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

8/10 Good
"Walls were thin and could hear our neighbors, but clean, and great priced hotel."
Sarah 1-night trip
Posted 1 hour ago
Comfort Inn South Portland Airport

Find out more about Chebeague Island

Search for holiday rentals in Chebeague Island on Expedia.co.uk! 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 holiday rentals in Chebeague Island?

Yes, there are holiday rentals close to the most popular sights in Chebeague Island, or you can select a more secluded option if you're looking for a relaxing stay. Chebeague Island is known for its shopping and restaurants.

How many holiday rentals are there in Chebeague Island?

Expedia has 5 holiday 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 Maine Narrow Gauge Railroad, or get out into nature at a spot like Winslow Memorial Park. Wolfe's Neck Woods State Park and Bailey Island Bridge are a couple of places you'll find in the wider area.

What are holiday rentals like in Chebeague Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chebeague Island. Holiday rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.