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Great Diamond Island 4 Stars Hotels

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Check availability on Great Diamond Island 4 Star Hotels

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Great Diamond Island 4-star hotels

Breakfast, lunch, dinner served; American cuisine
The Westin Portland Harborview

The Westin Portland Harborview

The Westin Portland Harborview
4.0 star property
Downtown Portland
8.8 out of 10, Excellent, (1004)
"Helpful and friendly staff"
United States
Wei Chien
The price is P5,767
P6,381 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Westin Portland Harborview
Restaurant
Portland Harbor Hotel

Portland Harbor Hotel

Portland Harbor Hotel
4.0 star property
Downtown Portland
9.2 out of 10, Wonderful, (1716)
"Beautiful room, friendly staff, and perfect location."
United States
Lisa
The price is P6,289
P9,199 total
includes taxes & fees
Dec 25 - Dec 26
Portland Harbor Hotel
Outdoor pool
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland
4.0 star property
South Portland
8.0 out of 10, Very Good, (1319)
"Very nice, fun pool, lovely staff"
United States
Sara
The price is P3,920
P4,272 total
includes taxes & fees
Jan 1 - Jan 2, 2026
DoubleTree by Hilton Hotel Portland
Exterior
Holiday Inn Portland-By the Bay by IHG

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, (1437)
"Every thing was perfect, service, accomodations, and friendly staff!!!"
United States
Michael
The price is P4,580
P5,068 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Portland-By the Bay by IHG
Bar (on property)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront
4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1003)
"Wonderful experience ... would definitely come back!"
United States
lynda
The price is P7,190
P7,955 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Canopy by Hilton Portland Waterfront
Breakfast, lunch, dinner served; American cuisine
The Press Hotel, Marriott Autograph Collection

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 P9,184
P10,161 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Press Hotel, Marriott Autograph Collection
Reception
Longfellow Hotel

Longfellow Hotel

Longfellow Hotel
4.0 star property
Parkside
9.6 out of 10, Exceptional, (139)
"Very stylish, clean, and comfortable hotel. We typically stay in the Oldport section of Portland but it was really nice to explore other areas. Lots of restaurants, bars, and coffee shops in the area. The hotel bar and coffee shop are great and very convenient. Look for those week day deals. Very affordable "
United States
Rachel
Longfellow Hotel
Breakfast and dinner served, American cuisine
Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks
4.0 star property
South Portland
8.4 out of 10, Very Good, (1000)
"Perfection! "
United States
Courtney
The price is P7,003
P7,633 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Portland Sheraton at Sable Oaks
Children's activities
Inn By The Sea

Inn By The Sea

Inn By The Sea
4.0 star property
Cape Elizabeth
9.4 out of 10, Exceptional, (293)
"Room was ready early friendly staff and room is better than expected "
United States
Jeff
Inn By The Sea
Private kitchen
The Weldon Hotel

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is P10,834
P16,213 total
includes taxes & fees
Dec 30 - Dec 31
The Weldon Hotel
Garden
Brewster House Bed & Breakfast

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 P9,795
P10,676 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Brewster House Bed & Breakfast
Living area
5 Seaview Ave

5 Seaview Ave

5 Seaview Ave
4.0 star property
Old Orchard Beach
5 Seaview Ave
View from property
Chebeague Island Inn

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
Street view
PineCrest Inn

PineCrest Inn

PineCrest Inn
4.0 star property
Gorham
9.8 out of 10, Exceptional, (103)
"Kathy, the owner, was very professional and runs a very nice Inn (B & B)."
United States
David
PineCrest Inn
Beach nearby
Bayview Beach Cottage For 4!

Bayview Beach Cottage For 4!

Bayview Beach Cottage For 4!
4.0 star property
Bay View
Bayview Beach Cottage For 4!
Private kitchen
The Coastal Nest Stay for 5!

The Coastal Nest Stay for 5!

The Coastal Nest Stay for 5!
4.0 star property
Blue Point
The Coastal Nest Stay for 5!
Living area
Latitude Adjustment Walk to Beach & Dining!

Latitude Adjustment Walk to Beach & Dining!

Latitude Adjustment Walk to Beach & Dining!
4.0 star property
Grand Beach
Latitude Adjustment Walk to Beach & Dining!
Living area
The Beach Bunker

The Beach Bunker

The Beach Bunker
4.0 star property
Old Orchard Beach
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...
United States
Robert
The Beach Bunker
Dining
Beachfront and Only 30 Steps To Beach!

Beachfront and Only 30 Steps To Beach!

Beachfront and Only 30 Steps To Beach!
4.0 star property
Bay View
Beachfront and Only 30 Steps To Beach!
Living area
Oceanfront Home - Beach Access - Deck + Ping Pong

Oceanfront Home - Beach Access - Deck + Ping Pong

Oceanfront Home - Beach Access - Deck + Ping Pong
4.0 star property
Old Orchard Beach
Oceanfront Home - Beach Access - Deck + Ping Pong
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Learn more about Great Diamond Island

Check out Sand Beach and Fifth Maine Museum—just a couple of the sights around Great Diamond Island.

See all hotels in Great Diamond Island
Summer on Casco Bay

Top Great Diamond Island Hotel Reviews

The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Staff was so friendly and had great dining recommendations. Room was super clean. Hotel was quiet and located in a perfect spot around the corner from the comedy show we went to see. Everything was so nice and good luck to the ginger bread house decoration competitors! We hope our choice wins!"
Samantha 1-night trip
Posted 3 days ago
The Westin Portland Harborview

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 vacation 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 P4,272

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 vacation experience where just about everything is included in one upfront price by using our "All inclusive" filter. Staying within budget is simple when your accommodations, 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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