Does Chebeague Island have any 4-star all-inclusive resorts?

Enjoy a worry-free holiday experience where everything is included in the upfront price by using our "All inclusive" filter. Sticking to your budget is simple when your room, meals and many activities are already taken care of. After something different? Check out the deals on our standard 4-star hotels in and around Chebeague Island too.

Are there any 4-star casino hotels in Chebeague Island?

To find your perfect escape in Chebeague Island, simply use our convenient filters to narrow down your search. Boasting resort-style amenities and a superior level of service, staying in a 4-star casino hotel is a safe bet for a good time.

Chebeague Island 4 Stars Hotels

Q: What are the best 4-star hotels in Chebeague Island?

Expedia customers love staying at Chebeague Island Inn . From its handy amenities to its welcoming staff, every feature of this 4-star hotel in Chebeague Island is designed to provide an incredible guest experience.

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Dates

February 2026

March 2026

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Our top choices for Chebeague Island 4-star hotels

Breakfast, lunch, dinner served; American cuisine

The Westin Portland Harborview

Downtown Portland

Kerrie

HK$845 total

includes taxes & fees

3 Feb - 4 Feb

Portland Harbor Hotel

Downtown Portland

Arturo

HK$1,217 total

includes taxes & fees

21 Jan - 22 Jan

DoubleTree by Hilton Hotel Portland

South Portland

Christopher

HK$567 total

includes taxes & fees

25 Jan - 26 Jan

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

Kimberly

HK$673 total

includes taxes & fees

29 Jan - 30 Jan

Canopy by Hilton Portland Waterfront

Downtown Portland

Kali

HK$920 total

includes taxes & fees

2 Feb - 3 Feb

The Press Hotel, Marriott Autograph Collection

Downtown Portland

Ryan

HK$1,423 total

includes taxes & fees

1 Feb - 2 Feb

Longfellow Hotel

Parkside

Rosanne

HK$1,410 total

includes taxes & fees

21 Jan - 22 Jan

Breakfast and dinner served, American cuisine

Portland Sheraton at Sable Oaks

South Portland

William

HK$1,011 total

includes taxes & fees

8 Feb - 9 Feb

Inn By The Sea

Cape Elizabeth

Jeff

HK$1,919 total

includes taxes & fees

26 Jan - 27 Jan

The Weldon Hotel

Downtown Portland

Eleni

HK$1,981 total

includes taxes & fees

2 Feb - 3 Feb

Brewster House Bed & Breakfast

Freeport

Olivia

HK$1,418 total

includes taxes & fees

5 Feb - 6 Feb

5 Seaview Ave

Old Orchard Beach

Chebeague Island Inn

Chebeague Island

Rob

PineCrest Inn

Gorham

David

The Coastal Nest Stay for 5!

Blue Point

Lakefront Retreat Near Portland – Modern Comfort with Classic Charm.

Falmouth

"Had a wonderful 1 week stay - this Vrbo had all the amenities we could ask for, and then some. Host was very welcoming and responsive to messages, and checked in with us in person on the first day to make sure we had everything we needed. Kitchen and bathrooms have all been renovated, along with a downstairs suite we didn’t need to use. Kitchen fully equipped and well stocked. Fresh herb garden on site as well! Beautiful lake views and easy water access - and close to Portland. We didn’t...

Kathleen C.

Latitude Adjustment Walk to Beach & Dining!

Grand Beach

The Beach Bunker

Old Orchard Beach

"This was my first long vacation I have done. First off, the host was amazing! Very good communication and very helpful. My family doesn’t like to leave a place dirty and we went to the beach a lot. I asked if it was possible to get a bigger broom & mop and she ordered them for us to use while we were there. This is also in a quiet spot on the strip. Overall was a fantastic spot to stay with a great host. If I could tweak a few minor things: water pressure is good but not strong. One other tweak...

Robert

Oceanfront Home - Beach Access - Deck + Ping Pong

Old Orchard Beach

Golf-front Personal Arcade Hot tub Outdoor Kitchen

Old Orchard Beach

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Learn more about Chebeague Island

Rent bikes to explore this peaceful island's rocky beaches and historic 1920s inn, where fresh lobster awaits. Take the passenger ferry from Cousins Island for a day trip, then kayak along the quiet coastline or hike wooded trails.

See all hotels in Chebeague Island