Plan your trip

A calm harbor with several sailboats anchored in the water.

Find 5 Star Hotels in Chebeague Island, ME from $93

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices

    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, December 14 – 15, 2026

    View in a map

    Top Chebeague Island Hotel Reviews

    The Harraseeket Inn & Event House Freeport Downtown

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

    Hampton Inn Freeport/Brunswick

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

    AC Hotel Portland Downtown/Waterfront, ME

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

    Hilton Garden Inn Freeport Downtown

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

    Hilton Garden Inn Portland Downtown Waterfront

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

    Inn By The Sea

    A backyard with a fire pit, wooden chairs, and a house with a porch.

    Embassy Suites by Hilton Portland Maine

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

    Cambria Hotel Portland Downtown-Old Port

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

    Portland Harbor Hotel

    A fire pit surrounded by wicker chairs in a garden setting.

    Canopy by Hilton Portland Waterfront

    An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.

    Inn On Peaks Island

    A two-story hotel with a balcony on the second floor, a sign reading "The Inn on Peaks Island," and a flag in front.

    The Press Hotel, Marriott Autograph Collection

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

    Evalina Hotel

    A multi-story building with a stone facade, large windows, and a corner entrance.

    Residence Inn by Marriott Portland Downtown/Waterfront

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

    Portland Regency Hotel & Spa

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

    The Weldon Hotel

    A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

    The Docent's Collection at 121 Middle Street

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

    Find out more about Chebeague Island

    There's nothing wrong with enjoying the finer things in life. Why not request the best on your excursion to Chebeague Island? There's no reason to delay a getaway to Chebeague Island any longer. You'll join the multitudes of vacationers who have made Chebeague Island so fashionable in the last few seasons. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Book one of Expedia's luxurious 5-star hotels in Chebeague Island and get ready to be pampered like never before.

    Get a Great Deal on 5-Star Hotels in Chebeague Island

    You'll have a wonderful time at one of these 5-star hotels. Michelin-starred restaurants, concierges, and pillow-fluffing are all at the ready. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready for a wonderful adventure. What creature comforts do you want in your lodging? A rejuvenating facial treatment to help your cares fall away? A concierge to help you make reservations at that outstanding restaurant? Beautiful furniture, delectable chocolate desserts, and even space for your family pet in some cases...these hotels will leave you amazed. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

    But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Chebeague Island are waiting for you to rest up after a busy day.

    Your Getaway Starts Today

    The results are in, and Chebeague Island 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Opt for one of the 5-star hotels in Chebeague Island today and settle down in the lap of luxury tomorrow.

    Frequently Asked Questions

    How much does it cost to stay in a 5-star hotel in Chebeague Island?

    The amount you pay for a 5-star hotel in Chebeague Island depends on factors like when you want to go and the length of your stay. Our top tip for scoring an awesome deal? Use our pricing filters to check out the available hotels for your chosen dates.

    What makes a hotel 5 stars in Chebeague Island?

    Exemplary guest service is the hallmark of every 5-star hotel in Chebeague Island. From the instant you arrive, staff cater to your every need, whether recommending activities and tours or providing in-room massages. Additionally, hotels have to feature top-rate amenities to obtain a 5-star rating. These can include luxury bathrobes, spas or saunas, pools, gourmet kitchens and knowledgeable concierge.

    Are there any 5-star all-inclusive resorts in Chebeague Island?

    Expedia's filter tool is the quickest way to find exactly what you want. Select "5-star" and "All inclusive" to show the finest resorts in Chebeague Island where your room, meals, activities and entertainment are included in the price. At these getaways, your trip is pure relaxation and indulgence from the moment you step foot in the lobby.

    Are there any 5-star vacation rentals in Chebeague Island?

    You won't find any 5-star vacation rentals in Chebeague Island on our site, but there are a few other top-rated options worth looking into. Search through our vacation rentals in Chebeague Island to book the ideal place for your stay.

    Explore a world of travel with Expedia