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

Compare and book 4 Star hotels in Bailey Island, Maine

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Check availability on Bailey Island 4 Star Hotels

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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.
The exterior of the Westin hotel with a prominent entrance and two bicycles parked in front.
A bar area with a long counter, multiple stools, and a variety of bottles and glasses.
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
6.232.642 ₫
6.895.796 ₫ total
includes taxes & fees
30 Aug - 31 Aug
The Westin Portland Harborview
A fire pit surrounded by wicker chairs in a garden setting.
A living room with a fireplace, seating area, and a large window.
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
John
6.950.858 ₫
8.685.496 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Portland Harbor Hotel
A conference room with a large screen displaying 'AFloat' and 'Holiday Inn by the bay'.
A modern bar area with a long counter, multiple seating options, and a built-in fire feature.
A swimming pool with lounge chairs and tables, surrounded by a well-lit indoor area with a view of the outside.
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
Sandra
5.319.912 ₫
5.885.951 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn Portland-By the Bay by IHG
An indoor swimming pool with a glass ceiling and blue lounge chairs around it.
A bar area with multiple screens displaying sports events, a selection of alcoholic beverages, and a pretzel with a drink on the counter.
A spacious restaurant with multiple dining areas, a bar, and a television screen displaying a tennis match.
A spacious lobby with leather booths, a reception desk, and a dining area with tables and chairs.

4. DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
South Portland
United States
Rosa
3.613.889 ₫
3.939.139 ₫ total
includes taxes & fees
7 Sept - 8 Sept
DoubleTree by Hilton Hotel Portland
An outdoor seating area with a fire feature, comfortable seating, and a view of the cityscape.
A modern living room with a fireplace, bookshelves, and comfortable seating.
A modern interior with wooden panel ceilings, a central seating area with sofas and tables, and a variety of decorative mirrors.
A modern interior with a fireplace, seating area, and large windows.

5. Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront
Downtown Portland
United States
Darlene
9.174.695 ₫
10.150.882 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Canopy by Hilton Portland Waterfront
A modern bar area with a long counter, multiple bar stools, and a variety of bottles and glasses.
An indoor swimming pool with a wooden ceiling, lounge chairs, and large windows offering a view of the outdoors.
A modern living room with a central fireplace, two sofas with patterned cushions, and a large window with a view of trees.

6. Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks
South Portland
United States
ajay
4.435.868 ₫
4.835.096 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Portland Sheraton at Sable Oaks
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
11.059.192 ₫
12.235.890 ₫ total
includes taxes & fees
30 Aug - 31 Aug
The Press Hotel, Marriott Autograph Collection
A modern bar area with a counter and stools, surrounded by patterned chairs and a blue sofa.
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
8.662.164 ₫
10.592.566 ₫ total
includes taxes & fees
1 Sept - 2 Sept
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 large, multi-story resort with a central building and several wings, situated near a beach and a lake.

9. Inn By The Sea

Inn By The Sea
Cape Elizabeth
United States
Victor W
12.887.610 ₫
15.119.245 ₫ total
includes taxes & fees
8 Sept - 9 Sept
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 room with a round wooden table, two chairs, a potted plant, a large window, and a round mirror on the wall.
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
9.181.895 ₫
11.964.491 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Weldon Hotel
An outdoor dining area with tables and chairs, overlooking a body of water and a sunset.
A cozy room with wooden ceilings, floral-patterned armchairs, a leather sofa, and a small table.
A boat docked near a building with a lawn and trees in the background.
A bar with wooden floors and hanging lights, bar stools, and a variety of bottles on shelves.

11. Chebeague Island Inn

Chebeague Island Inn
Chebeague Island
United States
Rob
4.178.484 ₫
5.010.001 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Chebeague Island Inn
A wooden outdoor seating area with a bench and a table, surrounded by trees and plants.
A sauna with wooden benches and a glass door.
A two-story house with a porch, a sign indicating it is a bed and breakfast, and a vacant sign.
A dining area with white tablecloths, wooden chairs, and a view of a park through large windows.

12. Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
Freeport
United States
Andrew
Brewster House Bed & Breakfast
A large, two-story house with a symmetrical facade, multiple windows, and a well-maintained lawn.
A living room with a fireplace, two patterned sofas, a coffee table, and a view of a lake through large glass doors.
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.

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

10/10 Excellent
"Beautiful hotel ,old style elegance . Blends in with old Portland area giving you top amenities,and top notch hospitality."
John 3-night trip
Posted 1 day ago
Portland Harbor Hotel
The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Good location, spacious rooms, excellent breakfast, very clean, great restaurant on the upper level, attentive and friendly staff. Loved our stay here."
Margaret 4-night trip
Posted 3 days ago
The Westin Portland Harborview

Frequently asked questions

What are the best 4-star hotels in Bailey Island?
Expedia customers highly recommend Chebeague Island Inn. From its handy amenities to its attentive service, every feature of this 4-star hotel in Bailey Island is designed to provide an awesome guest experience.
How much does it cost to stay in a 4-star hotel in Bailey Island?
We can help you easily locate the perfect 4-star hotel for your trip to Bailey Island. Use our filter tool to fine-tune your search by things like price, amenities and star rating and get access to fabulous deals in a few clicks.
  • Search for the lowest price from 3.939.139 ₫
What's the difference between 5-star and 4-star hotels in Bailey Island?
Offering a friendly guest experience and upscale surroundings, 4-star hotels are a wonderful option for your Bailey Island trip. These kinds of stays generally feature loads of handy amenities that make it easy to unpack and recharge — think 24-hour room service, gyms and restaurants. Or live the high life at a 5-star hotel designed to pamper with high-end perks and amenities. On-site health clubs, premium toiletries and gourmet dining are typically included at these plush properties.

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