4 Stars Hotels in Bailey Island, Maine from CA $103

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Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Bailey Island 4-star hotels

A grand piano in a spacious room with large windows, leather chairs, and a small table.

1. The Westin Portland Harborview

The Westin Portland Harborview
4.0 star property
Downtown Portland
9.0 out of 10, Wonderful, (1,012 reviews)
"Great hotel. Conveniently located to everything"
United States
Alan
The price is CA $129
CA $143 total
includes taxes & fees
Dec 6 - Dec 7
The Westin Portland Harborview
A fire pit surrounded by wicker chairs in a garden setting.

2. Portland Harbor Hotel

Portland Harbor Hotel
4.0 star property
Downtown Portland
9.2 out of 10, Wonderful, (1,875 reviews)
"Wonderful hotel!"
United States
Ann Lee
The price is CA $170
CA $242 total
includes taxes & fees
Nov 22 - Nov 23
Portland Harbor Hotel
A poolside area with lounge chairs, a table with a bottle and sunglasses, and a potted plant.

3. DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
4.0 star property
South Portland
8.2 out of 10, Very good, (1,462 reviews)
"Loved it here great food and close to everything you need."
United States
Stephen
The price is CA $104
CA $113 total
includes taxes & fees
Nov 29 - Nov 30
DoubleTree by Hilton Hotel Portland
A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.

4. Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
4.0 star property
Downtown Portland
9.0 out of 10, Wonderful, (1,683 reviews)
"We had a great stay… Recommended"
United States
Jake
The price is CA $131
CA $146 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Portland-By the Bay by IHG
Restaurant

5. Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks
4.0 star property
South Portland
8.4 out of 10, Very good, (1,000 reviews)
"I enjoyed my stay at this hotel. The property was clean, the grounds were beautiful, and my room was clean and comfortable. I would recommend staying here."
United States
Enedina
The price is CA $143
CA $156 total
includes taxes & fees
Dec 6 - Dec 7
Portland Sheraton at Sable Oaks
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.

6. The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection
4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1,000 reviews)
"Very nice hotel. Rooms on the smaller side, especially considering the price."
United States
Mark
The price is CA $270
CA $361 total
includes taxes & fees
Nov 22 - Nov 23
The Press Hotel, Marriott Autograph Collection
An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.

7. Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront
4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1,005 reviews)
"Great stay & great location!"
United States
Cal
The price is CA $216
CA $239 total
includes taxes & fees
Dec 8 - Dec 9
Canopy by Hilton Portland Waterfront
Reception

8. Longfellow Hotel

Longfellow Hotel
4.0 star property
Parkside
9.4 out of 10, Exceptional, (201 reviews)
"Easy Valet Parking, great staff and room service!"
United States
Ashley
The price is CA $316
CA $405 total
includes taxes & fees
Nov 15 - Nov 16
Longfellow Hotel
A backyard with a fire pit, wooden chairs, and a house with a porch.

9. Inn By The Sea

Inn By The Sea
4.0 star property
Cape Elizabeth
9.6 out of 10, Exceptional, (346 reviews)
"We had a wonderful stay at Inn By the Sea."
United States
Suzanne
The price is CA $292
CA $343 total
includes taxes & fees
Nov 12 - Nov 13
Inn By The Sea
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

10. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
The price is CA $257
CA $386 total
includes taxes & fees
Nov 20 - Nov 21
The Weldon Hotel
A wooden outdoor seating area with a bench and a table, surrounded by trees and plants.

11. Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (125 reviews)
"Breakfast was wonderful!"
United States
Julie
Brewster House Bed & Breakfast
A covered porch with a view of a lake and a grassy yard.

12. Chebeague Island Inn

Chebeague Island Inn
4.0 star property
Chebeague Island
8.8 out of 10, Excellent, (88 reviews)
"It’s a great place to get away from it all and enjoy beautiful views on the wrap around porch. The food is delicious. The place is laid back and quite lovely. I will be going back."
United States
Sarah
Chebeague Island Inn
A large, two-story house with a symmetrical facade, multiple windows, and a well-maintained lawn.

13. Waterfront Condo: Walk to Downtown Boothbay Harbor

Waterfront Condo: Walk to Downtown Boothbay Harbor
4.0 star property
Boothbay Harbor
Waterfront Condo: Walk to Downtown Boothbay Harbor

Top Bailey Island Hotel Reviews

A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
Downtown Portland

10/10 Excellent

Le service déjeunés étais parfait et tous est facile d’accès
Canada
Donovan
Reviewed August 20, 2026
Holiday Inn Portland-By the Bay by IHG

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 $103

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.

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

Finding your dream resort in Bailey Island is as simple as typing in your travel details and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your meals, room, entertainment and activities, or opt for a standard 4-star resort in or around this leading destination.

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

Use our handy filter tool to refine your Bailey Island search by amenities, star rating and much more. Whether you're looking for the full casino resort experience or just want to test out your luck while living it up in 4-star style, you're sure to find a stay that strikes just the right balance between entertainment and relaxation.

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