Chebeague Island, ME

Travel Guide

A wooden pier leading to a marina with boats docked.
A calm harbor with several sailboats anchored in the water.
A sunset over a calm lake with boats, a pier, and a grassy field.
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
$83 nightly
The price is $92 total per night from Nov 1 to Nov 2
$92 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,756 reviews)
"Would stay again!"

Reviewed on Oct 10, 2026

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
$135 nightly
The price is $149 total per night from Nov 1 to Nov 2
$149 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
$88 nightly
The price is $97 total per night from Oct 25 to Oct 26
$97 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,002 reviews)
"Great"

Reviewed on Oct 10, 2026

Fireside Inn & Suites Portland
See all 2,336 properties in Chebeague Island
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.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
54 York St Portland ME
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Cross Insurance Arena ...
9.8/10 Exceptional! (125 reviews)
"This was the best accommodation in Portland that we have stayed at—by a wide margin. The building and unit itself are a dream. Spacious, quiet, elevated, fresh, clean, thoughtful touches, quality finishes and materials, comfortable, inviting, secure…I have nothing but praise for this property. My ..."

Reviewed on Oct 9, 2026

The Weldon Hotel
Evalina Hotel

Evalina Hotel

2.5 out of 5
215 Commercial St Portland ME
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Maine Mall ...
10/10 Exceptional! (15 reviews)
"Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed ..."

Reviewed on Oct 5, 2026

Evalina Hotel
Oceanfront Studio w/ Private Dock in Harpswell!

Oceanfront Studio w/ Private Dock in Harpswell!

3 out of 5
Harpswell ME
Stay at this apartment in Harpswell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Mitchell Field and Bailey Island Bridge ...
Oceanfront Studio w/ Private Dock in Harpswell!
See all properties in Chebeague Island
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.

Frequently asked questions

When is the best time to visit Chebeague Island?
The best time to visit Chebeague Island is from June through August, when travelers can enjoy warm, pleasant weather. For fewer crowds and better value, the quieter months of November through January are a good option, offering cooler temperatures.
Can I book a refundable hotel in Chebeague Island?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chebeague Island by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chebeague Island with Expedia?
Expedia makes it easier to plan your Chebeague Island trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chebeague Island?
The best choice depends on your travel style. Hotels in Chebeague Island can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chebeague Island trip on Expedia?
Once you've booked your Chebeague Island trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chebeague Island trip?
Expedia offers customer support before, during, and after your Chebeague Island trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chebeague Island?
If it's your first trip to Chebeague Island, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chebeague Island hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chebeague Island hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chebeague Island

A sunset over a calm lake with a reflection of the sky and clouds, surrounded by a shoreline with sparse vegetation and a distant shoreline with buildings.

Yarmouth

A sunset over a lake surrounded by dense forests and a distant shoreline.

Long Island

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