A rocky shoreline with a boat, a house, and a forest in the background.

4 Stars Hotels in Bailey Island, Maine from CA $221

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Check availability on Bailey Island 4 Star Hotels

Tonight
Sep 3 - Sep 4
Tomorrow
Sep 4 - Sep 5
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Bailey Island 4-star hotels

A spacious lounge with leather seating, round tables, and large windows offering a view of a body of water and buildings.
A bar area with a long counter, multiple stools, and a variety of bottles and glasses.
The exterior of the Westin hotel with a prominent entrance and two bicycles parked in front.
A banquet hall with round tables, white tablecloths, and wooden chairs.

1. The Westin Portland Harborview

The Westin Portland Harborview
Downtown Portland
United States
Margaret
CA $270
CA $299 total
includes taxes & fees
Sep 7 - Sep 8
The Westin Portland Harborview
A fire pit surrounded by wicker chairs in a garden setting.
A dining area with round tables and chairs, a view of the garden through large windows, and a cozy atmosphere.
A hotel room with a large bed, two bedside tables, a chair, a window with curtains, and a view of the city.
A spacious living area with large windows, a staircase, and modern furniture.

2. Portland Harbor Hotel

Portland Harbor Hotel
Downtown Portland
United States
Brandon
CA $436
CA $535 total
includes taxes & fees
Sep 8 - Sep 9
Portland Harbor Hotel
A modern bar area with seating and a bar counter.
A swimming pool with lounge chairs and tables, surrounded by a well-lit indoor area with a view of the outside.
A modern bar area with a long counter, multiple seating options, and a built-in fire feature.
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.

3. Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
Downtown Portland
United States
DeeDee
CA $223
CA $247 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Portland-By the Bay by IHG
An indoor swimming pool with a wooden ceiling, lounge chairs, and large windows offering a view of the outdoors.
An outdoor patio area with tables and chairs, umbrellas, and a view of the surrounding greenery.
A modern living room with a central fireplace, two sofas with patterned cushions, and a large window with a view of trees.

4. Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks
South Portland
Canada
Peter
CA $247
CA $269 total
includes taxes & fees
Sep 13 - Sep 14
Portland Sheraton at Sable Oaks
An indoor swimming pool with a glass ceiling and blue lounge chairs around it.
A spacious lobby with leather booths, a reception desk, and a dining area with tables and chairs.
A stone sign with "DOUBLETREE BY HILTON" in front of a building with large windows and a landscaped garden.
A spacious restaurant with multiple dining areas, a bar, and a television screen displaying a tennis match.

5. DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
South Portland
United States
Sandra
CA $203
CA $221 total
includes taxes & fees
Sep 7 - Sep 8
DoubleTree by Hilton Hotel Portland
An outdoor seating area with a fire feature, comfortable seating, and a view of the cityscape.
A modern bar with a long counter, multiple bar stools, and a large window offering a view of the cityscape.
A modern living room with a fireplace, bookshelves, and comfortable seating.
A modern interior with a fireplace, seating area, and large windows.

6. Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront
Downtown Portland
United States
john
CA $536
CA $593 total
includes taxes & fees
Sep 20 - Sep 21
Canopy by Hilton Portland Waterfront
A modern interior with a bar area, seating, and shelves with plants and books.
A cozy living room with a fireplace, two green armchairs, a coffee table, and a yellow ottoman.
A modern living room with a large sectional sofa, a dining area with a kitchen in the background, and large windows offering a city view.
A rooftop terrace with a sofa, two chairs, and a small table, overlooking a cityscape and a body of water.

7. The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection
Downtown Portland
United States
Elizabeth
CA $640
CA $709 total
includes taxes & fees
Sep 20 - Sep 21
The Press Hotel, Marriott Autograph Collection
A modern bar area with a counter and stools, surrounded by patterned chairs and a blue sofa.
A wellness spa interior with a reception desk, potted plants, and wellness-related posters.
A multi-story brick building with a flat roof, large windows, and outdoor seating areas.
A hotel room with a bed, a small table, and a window with curtains.

8. Longfellow Hotel

Longfellow Hotel
Parkside
United States
Alexis
CA $522
CA $631 total
includes taxes & fees
Sep 8 - Sep 9
Longfellow Hotel
A backyard with a fire pit, wooden chairs, and a house with a porch.
A beach with several blue umbrellas and lounge chairs.
A balcony with a view of the sea, a pool, and a grassy area.
A wooden pathway surrounded by lush greenery and flowers, leading to a row of houses with a staircase.

9. Inn By The Sea

Inn By The Sea
Cape Elizabeth
United States
Victor W
CA $684
CA $802 total
includes taxes & fees
Sep 8 - Sep 9
Inn By The Sea
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.
A modern bedroom with a large bed, two bedside tables with lamps, a large abstract painting, a brick wall, and a window with a view of trees.
A multi-story brick building with a modern design, featuring large windows and a flat roof.

10. The Weldon Hotel

The Weldon Hotel
Downtown Portland
United States
Victoria
CA $528
CA $680 total
includes taxes & fees
Sep 21 - Sep 22
The Weldon Hotel
An outdoor dining area with tables and chairs, overlooking a body of water and a sunset.
A bar with wooden floors and hanging lights, bar stools, and a variety of bottles on shelves.
A cozy room with wooden ceilings, floral-patterned armchairs, a leather sofa, and a small table.
A beach with clear skies, calm water, and a distant ship.

11. Chebeague Island Inn

Chebeague Island Inn
Chebeague Island
United States
Rob
CA $280
CA $336 total
includes taxes & fees
Sep 29 - Sep 30
Chebeague Island Inn
A wooden outdoor seating area with a bench and a table, surrounded by trees and plants.
A garden with various flowers and a house in the background.
A dining area with white tablecloths, wooden chairs, and a view of a park through large windows.
A sauna with wooden benches and a glass door.

12. Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
Freeport
Brewster House Bed & Breakfast
A large, two-story house with a symmetrical facade, multiple windows, and a well-maintained lawn.
A modern kitchen with white cabinets, a built-in microwave, and a fire extinguisher.
A dining area with a wooden table, wicker chairs, and a chandelier.
A living room with a fireplace, two patterned sofas, a coffee table, and a view of a lake through large glass doors.

13. Waterfront Condo: Walk to Downtown Boothbay Harbor

Waterfront Condo: Walk to Downtown Boothbay Harbor
Boothbay Harbor
Waterfront Condo: Walk to Downtown Boothbay Harbor
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Learn more about Bailey Island

Hike the Giant's Stairs trail along the rocky coastline for dramatic views of Casco Bay. Seafood lovers shouldn't miss lobster rolls at Cook's Lobster & Ale House on the island's southern tip.

See all hotels in Bailey Island
A green netted buoy attached to a wooden post by a curved metal hook, with a wooden fence and a body of water in the background.

Top Bailey Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

8/10 Good
"Nice hotel. Room was comfortable. $35 dollar a day amenity charge that was unexpected-use in restaurant. $45 dollar a day valet parking in attached garage. Elevator slow and needs cleaning. Good location to seafront restaurants."
Camille 3-night trip
Posted 15 hours ago
Portland Harbor Hotel
The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Room and entire property was clean and well maintained. Staff was nice and helpful. There are two choices for parking: you can park in the garage yourself, just give your plate number at the front desk. You can also leave your car for valet parking in front of the hotel. Breakfast was very good. It’s not a continental breakfast, you order from a menu."
Inessa 2-night trip
Posted 3 days ago
The Westin Portland Harborview

Find out more about Bailey Island

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Bailey Island are calling your name. Known for providing first-rate service in amazing locations, each of the Bailey Island 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Bailey Island. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Bailey Island, Maine, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Bailey Island hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

What are the best 4-star hotels in Bailey Island?
Relax in refined comfort at Chebeague Island Inn. Based on Expedia guest reviews, this is one of Bailey Island's best 4-star hotels.
How much does it cost to stay in a 4-star hotel in Bailey Island?
Expedia can help you easily track down the perfect 4-star hotel for your getaway in Bailey Island. Use our filter tool to fine-tune your search by things like budget, amenities and hotel star rating and get access to terrific deals in a couple of clicks.
  • Search for the lowest price from CA $221
What's the difference between 5-star and 4-star hotels in Bailey Island?
If you choose to spend your vacation at a 4-star hotel in Bailey Island, you'll typically find loads of amenities to make sure you're relaxed, such as a pool, gym and restaurant. You can enjoy top-quality service and upscale accommodations. Choose a 5-star hotel and you'll have access to a few more perks — think concierge assistance, on-site spas and nightly turndown services. You'll most likely get additional amenities and first-rate services at a 5-star getaway, but both are awesome options for luxury guests.

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