Bailey Island 4 Stars Hotels

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Our top choices for Bailey Island 4-star hotels

Restaurant

Portland Harbor Hotel

Portland Harbor Hotel
4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1,783 reviews)
"Very nice accomodations, very pleasant and helpful staff, excellent location."
United States
Laverne
The price is NT$8,955
NT$11,116 total
includes taxes & fees
Jun 14 - Jun 15
Portland Harbor Hotel
Breakfast, lunch, dinner and brunch served

The Westin Portland Harborview

The Westin Portland Harborview
4.0 star property
Downtown Portland
9.0 out of 10, Wonderful, (1,011 reviews)
"Loved everything about the hotel. We Would definitely stay again."
United States
Amy L
The price is NT$8,521
NT$9,428 total
includes taxes & fees
Jul 1 - Jul 2
The Westin Portland Harborview
Outdoor pool

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
4.0 star property
South Portland
8.0 out of 10, Very Good, (1,411 reviews)
"Great hotel at a good location."
United States
Jacob
The price is NT$4,248
NT$4,630 total
includes taxes & fees
Jun 14 - Jun 15
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
9.0 out of 10, Wonderful, (1,602 reviews)
"Very nice hotel. Great room and view."
United States
Patti
The price is NT$6,304
NT$6,975 total
includes taxes & fees
Jun 21 - Jun 22
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, (1,008 reviews)
"Great stay and location!"
United States
Renee
The price is NT$11,201
NT$12,393 total
includes taxes & fees
Jun 30 - Jul 1
Canopy by Hilton Portland Waterfront
Breakfast, lunch, dinner and brunch served

The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection
4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1,001 reviews)
"Great bar. Fantastic pillows in the room. Good central location for walking."
United States
Dillon
The price is NT$10,596
NT$11,723 total
includes taxes & fees
Jul 5 - Jul 6
The Press Hotel, Marriott Autograph Collection
Breakfast and dinner served

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)
"Hotel staff was friendly. Room and gym were clean but had a few spots of grim, etc., that could’ve been cleaner."
United States
Kenneth
The price is NT$5,037
NT$5,490 total
includes taxes & fees
Jun 14 - Jun 15
Portland Sheraton at Sable Oaks
Reception

Longfellow Hotel

Longfellow Hotel
4.0 star property
Parkside
9.6 out of 10, Exceptional, (169 reviews)
"Clean, comfortable rooms. Hotel does have a few food options near by but car service was wonderful as it’s not near most of the restaurants & shops. Overall great hotel!"
United States
leah
The price is NT$10,805
NT$13,180 total
includes taxes & fees
Jun 14 - Jun 15
Longfellow Hotel
Children's activities

Inn By The Sea

Inn By The Sea
4.0 star property
Cape Elizabeth
9.6 out of 10, Exceptional, (319 reviews)
"Very nice place, very cclean and friendly."
United States
Victor W
The price is NT$14,421
NT$16,918 total
includes taxes & fees
Jun 14 - Jun 15
Inn By The Sea
Deluxe Suite, 1 King Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (101 reviews)
"Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"
United States
Roberta
The price is NT$11,385
NT$14,786 total
includes taxes & fees
Jul 6 - Jul 7
The Weldon Hotel
View from property

Chebeague Island Inn

Chebeague Island Inn
4.0 star property
Chebeague Island
8.8 out of 10, Excellent, (78 reviews)
"Great place to go and relax for a few days."
United States
Rob
The price is NT$7,193
NT$8,625 total
includes taxes & fees
Jun 15 - Jun 16
Chebeague Island Inn
Sauna

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (118 reviews)
"The food was wonderful and the hospitality was great!"
United States
Olivia
The price is NT$4,824
NT$5,258 total
includes taxes & fees
Jun 17 - Jun 18
Brewster House Bed & Breakfast
Apartment (2 Bedrooms) | Interior

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

Top Bailey Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

8/10 Good
"An older hotel. The room .. king facing the port. Lovely view but mattress is very soft and bathroom is small and old (cracks in porcelain of sink). No smart tv so couldn’t watch Netflix (used laptop). Breakfast included … amazing! Never had such a fresh array of excellent food including personal egg dishes made to order. There are electric bikes available for guests .. nice touch! Close to restaurants. About a 15 walk to waterfront. Staff was friendly and efficient."
Ian 3-night trip
Posted less than an hour ago
Holiday Inn Portland-By the Bay by IHG

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$4,630

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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