Compare and book 4 Star hotels in Bailey Island, Maine

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Bailey Island 4 Star Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Bailey Island 4 Star Hotels

View from property
The Westin Portland Harborview

The Westin Portland Harborview

4.0 star property
Downtown Portland
8.8 out of 10, Excellent, (1001)
"Helpful and friendly staff"
United States
Wei Chien
The price is 2.584.554 ₫
2.859.550 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Westin Portland Harborview
Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel

Portland Harbor Hotel

4.0 star property
Downtown Portland
9.2 out of 10, Wonderful, (1709)
"The location is perfect and the rooms are so comfortable. We enjoyed our stay! "
United States
Lisa
The price is 3.006.126 ₫
4.332.108 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Portland Harbor Hotel
Indoor pool
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4.0 star property
South Portland
8.0 out of 10, Very good, (1335)
"Staff were very attentive, breakfast had good choices. Great stay."
United States
Liliana
The price is 1.958.195 ₫
2.134.433 ₫ total
includes taxes & fees
11 Dec - 12 Dec
DoubleTree by Hilton Hotel Portland
Exterior
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4.0 star property
Downtown Portland
8.8 out of 10, Excellent, (1419)
"The staff was very helpful and the location was great!! "
United States
Donna
The price is 1.951.454 ₫
2.159.088 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Portland-By the Bay by IHG
Bar (on property)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1000)
"Yes great stay great staff"
United States
Douglas
The price is 3.222.253 ₫
3.565.100 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Canopy by Hilton Portland Waterfront
Royal Suite, 1 Bedroom | Frette Italian sheets, hypo-allergenic bedding, pillow-top beds
The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1000)
"Beautiful hotel, good & convenient restaurant and very short walk to Merrill Auditorium"
United States
PETER
The price is 4.124.737 ₫
4.563.609 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Press Hotel, Marriott Autograph Collection
Reception
Longfellow Hotel

Longfellow Hotel

4.0 star property
Parkside
9.6 out of 10, Exceptional, (133)
"Best hotel ever!! "
United States
Heather
Longfellow Hotel
Breakfast and dinner served, American cuisine
Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks

4.0 star property
South Portland
8.4 out of 10, Very good, (1000)
"Enjoyed our stay"
United States
Theresa
The price is 3.138.149 ₫
3.420.582 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Portland Sheraton at Sable Oaks
On the beach, fishing
Inn By The Sea

Inn By The Sea

4.0 star property
Cape Elizabeth
9.4 out of 10, Exceptional, (292)
"Room was ready early friendly staff and room is better than expected "
United States
Jeff
Inn By The Sea
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is 4.865.818 ₫
7.281.717 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Weldon Hotel
Garden
Brewster House Bed & Breakfast

Brewster House Bed & Breakfast

4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is 5.511.957 ₫
6.008.033 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Brewster House Bed & Breakfast
Sun-loungers, beach umbrellas, beach towels
Chebeague Island Inn

Chebeague Island Inn

4.0 star property
Chebeague Island
8.8 out of 10, Excellent, (77)
"Great place to go and relax for a few days."
United States
Rob
Chebeague Island Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
Bailey Island which includes general coastal views

Top Bailey Island Hotel Reviews

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 2.134.433 ₫

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.

Explore a world of travel with Expedia