The Best Hotels with Bars in Chebeague Island, ME from NT$2,735 in 2026

A calm harbor with several sailboats anchored in the water.

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Our top choices for Chebeague Island hotels with a bar

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

1. Hilton Garden Inn Freeport Downtown

Freeport

Jessica

NT$4,068 total

includes taxes & fees

Nov 29 - Nov 30

2. Inn On Peaks Island

Peaks Island

Alice

NT$4,802 total

includes taxes & fees

Nov 16 - Nov 17

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

3. The Harraseeket Inn & Event House Freeport Downtown

Freeport

sandra

NT$4,623 total

includes taxes & fees

Nov 16 - Nov 17

A modern interior with a wooden floor, a fireplace, and a seating area with chairs and a sofa.

4. Cambria Hotel Portland Downtown-Old Port

Downtown Portland

John

NT$4,359 total

includes taxes & fees

Dec 6 - Dec 7

An outdoor patio with a fire pit, string lights, and outdoor furniture.

5. Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

Nimayangi

NT$3,383 total

includes taxes & fees

Dec 1 - Dec 2

A modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.

6. AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

indriani

NT$3,237 total

includes taxes & fees

Nov 22 - Nov 23

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

7. Courtyard Portland Downtown/Waterfront

Downtown Portland

John

NT$3,317 total

includes taxes & fees

Dec 1 - Dec 2

A spacious lounge with leather seating, round tables, and large windows offering a view of a body of water and buildings.

8. The Westin Portland Harborview

Downtown Portland

Loretta

NT$3,307 total

includes taxes & fees

Dec 6 - Dec 7

A modern bar area with a bar counter, seating, and a view of the cityscape.

9. Aloft by Marriott Portland Downtown Waterfront ME

Downtown Portland

wendy

NT$3,026 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor patio with wicker furniture, a stone fireplace, and string lights.

10. Portland Harbor Hotel

Downtown Portland

Aliza

NT$5,644 total

includes taxes & fees

Nov 22 - Nov 23

View all properties

Top Chebeague Island Hotel Reviews

The Harraseeket Inn & Event House Freeport Downtown

Freeport

10/10 Excellent

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

Inn On Peaks Island

Peaks Island

10/10 Excellent

Devon

Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Mark

Cambria Hotel Portland Downtown-Old Port

Downtown Portland

10/10 Excellent

seth

A spacious lobby with multiple seating areas, a fireplace, and large windows.

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Michael

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Craig

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

Portland Regency Hotel & Spa

Downtown Portland

10/10 Excellent

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

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Christopher

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 Excellent

Robert

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

The Brunswick Hotel

Brunswick

10/10 Excellent

Anonymous traveler

Courtyard Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Anonymous traveler

A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

10/10 Excellent

Sherry

A spacious living area with a curved staircase, a round glass coffee table, and a seating arrangement.

The Federal

Brunswick

10/10 Excellent

Ryan

West End Collection at 146 Pine

West End

10/10 Excellent

Constance

The Westin Portland Harborview

Downtown Portland

10/10 Excellent

Lawrence

A modern interior with a bar area, seating, and shelves with plants and books.

The Press Hotel, Marriott Autograph Collection

Downtown Portland

10/10 Excellent

RII

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

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Excellent

Douglas

A beach with several blue umbrellas and lounge chairs.

Inn By The Sea

Cape Elizabeth

10/10 Excellent

James

Frequently Asked Questions

Searching for hotels with bars in Chebeague Island?

Though you might not find a hotel in Chebeague Island well-known for its bar, you will find 9 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're in the area, consider a visit to Little John Island Preserve and Wolfe's Neck Woods State Park.

What are the best hotels with bars in Chebeague Island?

Below are some of top hotels with bars in and around Chebeague Island: Quality Inn & Suites South Portland: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and 3 coffee shops. Clarion Hotel Portland Airport ME: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. Clarion Pointe South Portland: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. Portland Harbor Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and full-service spa.

What is there to do in Chebeague Island?

If you have time to explore, consider visiting Little John Island Preserve, Wolfe's Neck Woods State Park, and Bailey Island Bridge, and then find a cozy spot for a nightcap. Other places to see in the area include Casco Bay and Sand Beach.

When is the best time to visit Chebeague Island?

Visiting local bars in Chebeague Island is more fun when you know what the weather holds. These rainfall averages and temperatures can help you decide the best time for bar hopping. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chebeague Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.

How can I get to Chebeague Island and around the area?

You might want to make the most of these transportation choices in and around Chebeague Island: Fly into Portland Intl. Jetport Airport (PWM), which is located 12.1 mi (19.4 km) from the city center. Otherwise, you can search for flights to Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

Find Hotels with Bars in Chebeague Island, ME

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chebeague Island hotels with a bar

1. Hilton Garden Inn Freeport Downtown

2. Inn On Peaks Island

3. The Harraseeket Inn & Event House Freeport Downtown

4. Cambria Hotel Portland Downtown-Old Port

5. Residence Inn by Marriott Portland Downtown/Waterfront

6. AC Hotel Portland Downtown/Waterfront, ME

7. Courtyard Portland Downtown/Waterfront

8. The Westin Portland Harborview

9. Aloft by Marriott Portland Downtown Waterfront ME

10. Portland Harbor Hotel

Top Chebeague Island Hotel Reviews

The Harraseeket Inn & Event House Freeport Downtown

10/10 Excellent

Frequently Asked Questions

Searching for hotels with bars in Chebeague Island?

What are the best hotels with bars in Chebeague Island?

What is there to do in Chebeague Island?

When is the best time to visit Chebeague Island?

How can I get to Chebeague Island and around the area?

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