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

Bailey Island 4 Stars Hotels

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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.

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 NT$2,988
NT$3,306 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 NT$3,961
NT$5,635 total
includes taxes & fees
Nov 22 - Nov 23
Portland Harbor Hotel
An indoor swimming pool with a glass ceiling and blue lounge chairs around it.

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 NT$2,395
NT$2,611 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 NT$3,041
NT$3,381 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 NT$3,325
NT$3,624 total
includes taxes & fees
Nov 29 - Nov 30
Portland Sheraton at Sable Oaks
A modern interior with a bar area, seating, and shelves with plants and books.

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 NT$6,250
NT$8,358 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 NT$4,949
NT$5,476 total
includes taxes & fees
Dec 8 - Dec 9
Canopy by Hilton Portland Waterfront
A modern bar area with a counter and stools, surrounded by patterned chairs and a blue sofa.

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 NT$7,356
NT$9,408 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 NT$6,774
NT$7,947 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 NT$6,007
NT$9,010 total
includes taxes & fees
Dec 2 - Dec 3
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
An outdoor dining area with tables and chairs, overlooking a body of water and a sunset.

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
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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

The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Nice property. High parking fees"
SCOTT 1-night trip
Posted 3 hours 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 NT$2,611

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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