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

Find 4 Star Hotels in Bailey Island, ME from $80

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Check availability on Bailey Island 4 Star Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 banquet hall with round tables, white tablecloths, and wooden chairs.
The exterior of the Westin hotel with a prominent entrance and two bicycles parked in front.
A modern hotel lobby with a large chandelier, reception desk, and a staircase leading to other areas.

1. The Westin Portland Harborview

The Westin Portland Harborview
Downtown Portland
United States
Samuel
$127 nightly
$141 total
Nov 11 - Nov 12
Total with taxes and fees
The Westin Portland Harborview
A fire pit surrounded by wicker chairs in a garden setting.
A hotel room with a large bed, two bedside tables, a chair, a window with curtains, and a view of the city.
A dining area with round tables and chairs, a view of the garden through large windows, and a cozy atmosphere.
A living room with a fireplace, seating area, and a large window.

2. Portland Harbor Hotel

Portland Harbor Hotel
Downtown Portland
United States
Teresa
$207 nightly
$228 total
Nov 1 - Nov 2
Total with taxes and fees
Portland Harbor Hotel
A modern bar area with a long counter, multiple seating options, and a built-in fire feature.
A Holiday Inn hotel with a modern design, featuring a large entrance canopy and multiple floors.
A swimming pool with lounge chairs and tables, surrounded by a well-lit indoor area with a view of the outside.
A conference room with a stage featuring a large screen displaying the word 'Float' and a banner for the University of Maine.

3. Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
Downtown Portland
United States
Fran
$102 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Portland-By the Bay by IHG
Restaurant
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.

4. Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks
South Portland
United States
Enedina
$118 nightly
$129 total
Nov 15 - Nov 16
Total with taxes and fees
Portland Sheraton at Sable Oaks
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 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.

5. DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
South Portland
United States
Amy
$73 nightly
$80 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Hotel Portland
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 rooftop terrace with a sofa, two chairs, and a small table, overlooking a cityscape and a body of water.
A modern restaurant with a bar area, wooden tables, and leather booths.

6. The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection
Downtown Portland
United States
Mark
$239 nightly
$264 total
Nov 8 - Nov 9
Total with taxes and fees
The Press Hotel, Marriott Autograph Collection
Bar (on property)
Exterior
A modern hotel room with a large bed, a wooden headboard, a bedside table with a lamp, and a view of the outdoors through a window.
A modern living room with a fireplace, sofas, a coffee table, and a bookshelf.

7. Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront
Downtown Portland
United States
Abdolkarim
$177 nightly
$196 total
Nov 11 - Nov 12
Total with taxes and fees
Canopy by Hilton Portland Waterfront
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 hotel room with a bed, a small table, and a window with curtains.
A multi-story brick building with a flat roof, large windows, and outdoor seating areas.

8. Longfellow Hotel

Longfellow Hotel
Parkside
United States
thomas
$244 nightly
$270 total
Nov 1 - Nov 2
Total with taxes and fees
Longfellow Hotel
A backyard with a fire pit, wooden chairs, and a house with a porch.
A large, multi-story resort with a central building and several wings, situated near a beach and a lake.
A beach with several blue umbrellas and lounge chairs.
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
Kathleen
$374 nightly
$408 total
Nov 11 - Nov 12
Total with taxes and fees
Inn By The Sea
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.
A multi-story brick building with a modern design, featuring large windows and a flat roof.
A room with a round wooden table, two chairs, a potted plant, a large window, and a round mirror on the wall.
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.

10. The Weldon Hotel

The Weldon Hotel
Downtown Portland
United States
Victoria
$291 nightly
$310 total
Nov 3 - Nov 4
Total with taxes and fees
The Weldon Hotel
An outdoor dining area with tables and chairs, overlooking a body of water and a sunset.
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.
A beach with clear skies, calm water, and a distant ship.

11. Chebeague Island Inn

Chebeague Island Inn
Chebeague Island
United States
Rob
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 sauna with wooden benches and a glass door.
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
Julie
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 dining area with a wooden table, wicker chairs, and a chandelier.
A residential property with a well-maintained lawn, outdoor seating, and a view of a lake.

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 wooden bridge over water with a yellow kayak, boats, and a motel in the background.

Top Bailey Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The room was beautiful, clean and comfortable. The most comfortable hotel beds we have slept in this trip. Front desk staff was extremely helpful and kind. Loved that they have a shuttle to take you to the hotspots so you don’t have to move your car and pay for parking."
James 1-night trip
Posted 21 hours ago
Holiday Inn Portland-By the Bay by IHG
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

8/10 Good
"Location is next to a shopping center on the decline and across the street from a busy Starbucks. There was an overnight delivery truck left running outside our window that kept us awake. The bed was softer that we prefer and we woke up with a backache. Pool is much smaller than the pictures make it look. Breakfast was very good."
Laura 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Portland

Find out more about Bailey Island

Bailey Island Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Bailey Island, Maine are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Bailey Island 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Bailey Island. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Bailey Island, Maine, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Bailey Island hotels offer everything your heart desires.

Frequently asked questions

What are the best 4-star hotels in Bailey Island?
Relax in refined comfort at Chebeague Island Inn. Based on reviews by our guests, this is one of Bailey Island's favorite 4-star hotels.
How much does it cost to stay in a 4-star hotel in Bailey Island?
To find a 4-star hotel in Bailey Island that fits your budget, take advantage of Expedia's search and sort filters. Check out the availability during your preferred dates and use our pricing filter to set your limit. You can also sort your results by the most budget-friendly stay first.
  • Search for the lowest price from $80
What's the difference between 5-star and 4-star hotels in Bailey Island?
Treat yourself to luxury during your Bailey Island vacation by checking in to a 4-star hotel. As well as featuring upscale accommodations, these properties are typically packed with amenities, including bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and special one. 24-hour front desk, luxurious spas and gourmet dining are a few of the first-rate services and conveniences you'll likely be able to enjoy.

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