A calm harbor with several sailboats anchored in the water.

Hotels in Chebeague Island

Q: What accommodations do travelers recommend in Chebeague Island?

Guests like Portland Harbor Hotel , Holiday Inn Portland-By the Bay by IHG and Cambria Hotel Portland Downtown-Old Port .

Where to?

Dates

October 2026

November 2026

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Where to stay in Chebeague Island?

An outdoor dining area with tables and chairs, overlooking a body of water and a sunset.

1. Chebeague Island Inn

Chebeague Island

$318 total

includes taxes & fees

Oct 1 - Oct 2

A Holiday Inn Express building with a covered entrance, multiple floors, and a clear sky.

2. Holiday Inn Express Hotel & Suites Freeport by IHG

Freeport

$121 total

includes taxes & fees

Oct 28 - Oct 29

A swimming pool with clear blue water, surrounded by large windows offering views of trees and a clear sky.

3. Hampton Inn Freeport/Brunswick

Freeport

$120 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a bed, bedside tables, a television, and artwork on the wall.

4. Spark by Hilton Freeport

Freeport

$124 total

includes taxes & fees

Oct 18 - Oct 19

A modern living room with a sofa, ottoman, and chairs, a kitchen area with a counter and pendant lights, and a large window with curtains.

5. The Freeport Hotel, an Ascend Collection Hotel

Freeport

$102 total

includes taxes & fees

Oct 26 - Oct 27

A breakfast buffet with pastries, coffee, and condiments.

6. Econo Lodge Freeport - Brunswick Area

Freeport

$108 total

includes taxes & fees

Oct 1 - Oct 2

A modern living room with dark blue walls, large windows, and a view of a landscaped garden.

7. Best Western Freeport Inn

Freeport

$125 total

includes taxes & fees

Oct 4 - Oct 5

A hotel room with a large bed, a desk with a chair, a TV, and a window with curtains.

8. Hilton Garden Inn Freeport Downtown

Freeport

$152 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel lobby with a central bar area, multiple seating arrangements, and large windows providing views of the outside.

9. SpringHill Suites by Marriott Freeport Brunswick

Freeport

$154 total

includes taxes & fees

Oct 18 - Oct 19

A two-story building with a large glass conservatory and yellow umbrellas in the garden area.

10. The Harraseeket Inn & Event House Freeport Downtown

Freeport

$173 total

includes taxes & fees

Oct 6 - Oct 7

A multi-story hotel with 'Resilience Inn' and 'Mozy Hotels' signage, featuring a modern brick facade and multiple ground-level retail spaces.

11. Moxy Portland Thompson's Point

Portland

$158 total

includes taxes & fees

Oct 29 - Oct 30

A rooftop terrace with a modern outdoor seating area, a fire pit, and a view of the cityscape.

12. Cambria Hotel Portland Downtown-Old Port

Downtown Portland

$212 total

includes taxes & fees

Oct 25 - Oct 26

A large, multi-story building with a central courtyard, featuring a fire pit and outdoor seating area.

13. Inn at Diamond Cove

Portland

$364 total

includes taxes & fees

Oct 1 - Oct 2

A view from a window overlooking a body of water with a distant shoreline, a vase with flowers, and a glass on a table.

14. The McKernan Inn

South Portland

$243 total

includes taxes & fees

Oct 19 - Oct 20

A balcony with wooden flooring, striped cushioned chairs, and a glass railing overlooking a cityscape at night.

15. Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

$165 total

includes taxes & fees

Oct 29 - Oct 30

A Travelers Inn with a white exterior, green trim, and a prominent sign.

16. Travelers Inn

Brunswick

$108 total

includes taxes & fees

Oct 8 - Oct 9

A hotel room with a bed, a TV, a desk, and a view of a lighthouse through a mural.

17. Clarion Pointe South Portland

Thorton Heights

$59 total

includes taxes & fees

Oct 19 - Oct 20

An outdoor patio area with wicker furniture, string lights, and a barbecue grill.

18. Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

$187 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with two beds, a TV, a desk, and a lamp.

19. Moonlight Inn

Brunswick

$101 total

includes taxes & fees

Oct 1 - Oct 2

The exterior of a Courtyard by Marriott hotel with a glass entrance, outdoor seating area, and a stone facade.

20. Courtyard Portland Downtown/Waterfront

Downtown Portland

$167 total

includes taxes & fees

Oct 25 - Oct 26

View all properties

Go beyond your typical stay in Chebeague Island

Learn more about Chebeague Island

The region around Chebeague Island is home to attractions such as Little John Island Preserve and Wolfe's Neck Woods State Park.

See all hotels in Chebeague Island

Check out reviews of Chebeague Island hotels guests love

Hampton Inn Freeport/Brunswick

Freeport

10/10 Exceptional

Dwight

Spark by Hilton Freeport

Freeport

10/10 Exceptional

Jane

The Harraseeket Inn & Event House Freeport Downtown

Freeport

10/10 Exceptional

Going to the Harraseeket Inn is like time traveling, but with the option of taking a smart phone and having the electricity to charge it. It's like that movie, "Somewhere in Time," like you've walked through a time portal by the power of hypnotic suggestion and an Expedia booking. But it is very much, at the same time, part of the present. They have a pool, and the restaurant is quintessentially the definition of a timeless Maine eatery. The afternoon tea is pleasant and steeped with charm. The...

Bruno

The McKernan Inn

South Portland

10/10 Exceptional

elizabeth

The Freeport Hotel, an Ascend Collection Hotel

Freeport

10/10 Exceptional

Mark

Candlebay Inn

Freeport

10/10 Exceptional

Sheree Lee

Cambria Hotel Portland Downtown-Old Port

Downtown Portland

10/10 Exceptional

seth

A balcony with a table and chairs, overlooking a street with buildings and parked cars.

Portland Regency Hotel & Spa

Downtown Portland

10/10 Exceptional

This property is beautiful. It sits in the historic area of the old port. It is very close to the waterfront, restaurants, shops and historic areas. The mattress and sheets were superb. While in the old port, we took a trolley tour which took us out to Portland headlight and then gave us a tour of of the old port. You can catch fairies from about two or three minutes walk away, we would strongly recommend this hotel.

Debra

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Exceptional

Douglas

A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

10/10 Exceptional

Robert

Inn at Diamond Cove

Portland

10/10 Exceptional

We arrived at the Portland Airport and caught a 20 minute Uber to the Casco Ferry. A short ferry ride to this very quiet island. The Hotel is within an old Military base gentrified. Staff were fantastic and the food was good ,not great, but always available and the dining areas are elegant. The rooms and lobby area lived up to the photos. Recreation consisted of pool and hot tub, small restaurant and bar area, free bikes and hiking. Plan to relax. There is another restaurant near the ferry...

Bruce & Louise

A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.

The Docent's Collection at 121 Middle Street

Downtown Portland

10/10 Exceptional

Jeffrey

A brick building with a sign reading "WAYPOINT" and outdoor seating with tables, chairs, and a fire pit.

Embassy Suites by Hilton Portland Maine

Portland

10/10 Exceptional

Michael

A restaurant with long tables, chairs, and hanging plants.

The Federal

Brunswick

10/10 Exceptional

Ryan

An outdoor patio with seating, a fire feature, and string lights.

The Brunswick Hotel

Brunswick

10/10 Exceptional

Anonymous traveler

Frequently Asked Questions

What accommodations do travelers recommend in Chebeague Island?

Guests like Portland Harbor Hotel, Holiday Inn Portland-By the Bay by IHG and Cambria Hotel Portland Downtown-Old Port.

Can I book a refundable hotel in Chebeague Island?

If you need the flexibility to change your plans to Chebeague Island, most hotels offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Chebeague Island if I want a vacation rental instead of a hotel?

If you want to find a good alternative to a hotel, browse our selection of 5 vacation homes.

What will the weather in Chebeague Island be like during my trip?

July and August are typically the warmest months in Chebeague Island when the average temp is 65°F. January and February are the coldest months when the average temperature is 30°F. October and December are the months with the most rain.

Why should I book my Chebeague Island hotel with Hotels.com?

There are lots of reasons to book your Chebeague Island trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.