Photo by Robbie Martin

4 Star Hotels in Great Diamond Island, Portland

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Top Great Diamond Island 4 Star Hotels

Our top choices for Great Diamond Island 4-star hotels

Holiday Inn Portland-By the Bay by IHG
Exterior

Holiday Inn Portland-By the Bay by IHG

4.0 star property
8.8 out of 10, Excellent, (1375)
"Staff was wonderful and the room was perfect!! Will definitely stay there again!!"
The price is €168
includes taxes & fees
20 Oct - 21 Oct
Holiday Inn Portland-By the Bay by IHG
Canopy by Hilton Portland Waterfront
Bar (on property)

Canopy by Hilton Portland Waterfront

4.0 star property
9.4 out of 10, Exceptional, (1011)
"Great experience, friendly staff and wonderful accommodations close to all. "
The price is €321
includes taxes & fees
20 Oct - 21 Oct
Canopy by Hilton Portland Waterfront
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1593)
"Staff was super friendly & helpful, and the hotel was great!"
The price is €328
includes taxes & fees
20 Oct - 21 Oct
Portland Harbor Hotel
The Westin Portland Harborview
View from property

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1003)
"Great for a short stay!"
The price is €235
includes taxes & fees
20 Oct - 21 Oct
The Westin Portland Harborview
DoubleTree by Hilton Hotel Portland
Indoor pool

DoubleTree by Hilton Hotel Portland

4.0 star property
8.0 out of 10, Very good, (1251)
"Clean and the staff was very helpful. "
The price is €141
includes taxes & fees
22 Oct - 23 Oct
DoubleTree by Hilton Hotel Portland
The Press Hotel, Marriott Autograph Collection
Royal Suite, 1 Bedroom

The Press Hotel, Marriott Autograph Collection

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Close to Old Port. Great restaurants nearby."
The price is €339
includes taxes & fees
13 Oct - 14 Oct
The Press Hotel, Marriott Autograph Collection
Portland Sheraton at Sable Oaks
Breakfast and dinner served, American cuisine

Portland Sheraton at Sable Oaks

4.0 star property
8.4 out of 10, Very good, (1003)
"Enjoyed our stay"
The price is €165
includes taxes & fees
19 Oct - 20 Oct
Portland Sheraton at Sable Oaks
Longfellow Hotel
Reception

Longfellow Hotel

4.0 star property
9.6 out of 10, Exceptional, (119)
"Fabulous hotel, wonderful staff with a fabulous cafe attached for breakfast. "
Longfellow Hotel
Inn By The Sea
On the beach, fishing

Inn By The Sea

4.0 star property
9.4 out of 10, Exceptional, (281)
"Absolutely 5 star. Best bed I’ve slept in at a hotel bar none. "
Inn By The Sea
The Weldon Hotel
Deluxe Suite, 1 King Bed | Living area

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (79)
"Absolutely beautiful place to stay. "
The price is €337
includes taxes & fees
1 Oct - 2 Oct
The Weldon Hotel
Chebeague Island Inn
Sun-loungers, beach umbrellas, beach towels

Chebeague Island Inn

4.0 star property
8.8 out of 10, Excellent, (77)
"Great place to go and relax for a few days."
Chebeague Island Inn
Brewster House Bed & Breakfast
Garden

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
The price is €277
includes taxes & fees
25 Sept - 26 Sept
Brewster House Bed & Breakfast
5 Seaview Ave
Family House | Private kitchen

5 Seaview Ave

4.0 star property
5 Seaview Ave
PineCrest Inn
Street view

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (103)
"Lovely home, great breakfast. Kathy is a very gracious hostess and really helped us to thoroughly enjoy the Portland area."
PineCrest Inn
The Beach Bunker
Deluxe Condo | Private kitchen

The Beach Bunker

4.0 star property
10.0 out of 10, Exceptional, (2)
"This was my first long vacation I have done. First off, the host was amazing! Very good communication and very helpful. My family doesn’t like to leave a place dirty and we went to the beach a lot. I asked if it was possible to get a bigger broom & mop and she ordered them for us to use while we were there. This is also in a quiet spot on the strip. Overall was a fantastic spot to stay with a great host. If I could tweak a few minor things: water pressure is good but not strong. One other tweak...
The Beach Bunker
Bayview Beach Cottage For 4!
Beach nearby

Bayview Beach Cottage For 4!

4.0 star property
Bayview Beach Cottage For 4!
Lakefront Retreat Near Portland – Modern Comfort with Classic Charm.
Interior

Lakefront Retreat Near Portland – Modern Comfort with Classic Charm.

4.0 star property
10.0 out of 10, Exceptional, (3)
"Had a wonderful 1 week stay - this Vrbo had all the amenities we could ask for, and then some. Host was very welcoming and responsive to messages, and checked in with us in person on the first day to make sure we had everything we needed. Kitchen and bathrooms have all been renovated, along with a downstairs suite we didn’t need to use. Kitchen fully equipped and well stocked. Fresh herb garden on site as well! Beautiful lake views and easy water access - and close to Portland. We didn’t...
Lakefront Retreat Near Portland – Modern Comfort with Classic Charm.
Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of Downtown Portland
Beach

Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of Downtown Portland

4.0 star property
10.0 out of 10, Exceptional, (89)
"Absolutely charming home in a great location. Equally lovely homeowner/host. Highly recommend."
Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of Downtown Portland
Oceanfront Home - Beach Access - Deck + Ping Pong
House, Multiple Beds, Patio, Ocean View (Ocean Sunrise) | Dining

Oceanfront Home - Beach Access - Deck + Ping Pong

4.0 star property
Oceanfront Home - Beach Access - Deck + Ping Pong
Beachfront and Only 30 Steps To Beach!
Beach nearby

Beachfront and Only 30 Steps To Beach!

4.0 star property
Beachfront and Only 30 Steps To Beach!
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Learn more about Great Diamond Island

Check out Sand Beach and East End Beach—just a couple of the sights around Great Diamond Island.

See all hotels in Great Diamond Island
Photo by Robbie Martin
Open Photo by Robbie Martin

Top Great Diamond Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Perfect!! Clean, friendly , accommodating!! And the restaurant food was delicious!"
Rebecca 1-night trip
Posted 3 days ago
Portland Harbor Hotel

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Great Diamond Island?
We can help you quickly find the ideal 4-star hotel for your holiday in Great Diamond Island. Use our handy filter tool to fine-tune your search by things like price, conveniences and star rating and get access to fantastic deals in a couple of clicks.

  • Search for the lowest price from €141

What's the difference between 5-star and 4-star hotels in Great Diamond Island?
Treat yourself to luxury living during your Great Diamond Island escape by checking in to a 4-star hotel. As well as featuring upscale surroundings, these properties are usually filled with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and special one. Concierge assistance, luxurious spas and world-class dining are just the start of the first-rate conveniences and services you'll likely have access to.
Does Great Diamond Island have any 4-star all-inclusive resorts?
Enjoy a worry-free holiday experience where just about everything is included in one upfront price by using our "All inclusive" filter. Staying within budget is simple when your accommodation, meals and many activities are already taken care of. Want more options? Check out the incredible offers on our standard 4-star stays in and around Great Diamond Island too.

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