A calm sea with a sailboat and rocky coastline.

Great Diamond Island Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Great Diamond Island holiday rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (118 reviews)
"Really nice room and location"
United States
Victoria
The price is HK$2,986
HK$3,843 total
includes taxes & fees
22 Sept - 23 Sept
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is HK$4,336
HK$5,902 total
includes taxes & fees
15 Sept - 16 Sept
Evalina Hotel

3. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is HK$2,353
HK$3,616 total
includes taxes & fees
15 Sept - 16 Sept
Ocean View East End Studio in a Historic Victorian
A street lined with buildings, one with a red door and a sign that reads "MINATO".

4. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (183 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is HK$1,980
HK$3,209 total
includes taxes & fees
16 Sept - 17 Sept
Glorious getaway on Portland's Eastern Promenade.
A room with a wooden bench, a red guitar, and a plant on a table.

5. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
The price is HK$2,814
HK$6,435 total
includes taxes & fees
16 Sept - 17 Sept
Prime Old Port 3BR • Free Parking • Sleeps 8
A two-story house with a balcony, a covered patio, and a fenced yard.

6. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is HK$2,800
HK$5,052 total
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

7. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (27 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is HK$1,372
HK$2,265 total
includes taxes & fees
5 Oct - 6 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A beach with a wooden chair and a small building in the background.

8. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is HK$4,489
HK$7,218 total
includes taxes & fees
1 Oct - 2 Oct
Arlie`s Digs! - One Block To Willard Beach!
A wooden bench on a rocky shore overlooking a calm body of water.

9. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is HK$1,870
HK$3,210 total
includes taxes & fees
22 Sept - 23 Sept
City Amenities, Casco Bay Sunrises and Natural Beauty
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

10. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is HK$2,386
HK$3,995 total
includes taxes & fees
15 Sept - 16 Sept
Modern & Sunny House Steps from the Promenade.
A modern living room with a brown leather sofa, a wooden sliding door, and a framed artwork on the wall.

11. Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (55 reviews)
"Everything from booking to checkout was outstanding! Very clean, great location, easy parking and walking to town. The host quickly communicates; highly recommend this place for your stay in Portland!"
United States
Kirsten Z.
The price is HK$4,183
HK$6,774 total
includes taxes & fees
29 Sept - 30 Sept
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
A harbor with boats docked, a pier, and buildings in the background.

12. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay at Mat's place! Convenient location, very cute apartment with a lovely view of the water. Well equipped for a couple's weekend away. We appreciated the sharp knives for cooking and the comfy couch!"
United States
Charlotte B.
Casco Bay Vista
A hallway leading to a bedroom with a bed, a desk, and a chair. There is a framed picture on the wall and a bench in the corner.

13. Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful apartment. Great location. Very comfortable and all amenities needed."
United States
Navina F.
The price is HK$3,360
HK$5,491 total
includes taxes & fees
15 Sept - 16 Sept
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
A modern kitchen with a central island, bar stools, pendant lighting, and a large refrigerator.

14. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"5 star in every way"
United States
Doug F.
The price is HK$4,466
HK$6,834 total
includes taxes & fees
15 Sept - 16 Sept
Harborview - Curated East End Escape w/ Parking
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

15. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (42 reviews)
"Very comfortable and stocked well. Lacked for nothing and able to walk to most places. Host checked in which was very nice. Enjoyed Portland."
United States
sheila g.
The price is HK$2,223
HK$3,555 total
includes taxes & fees
24 Sept - 25 Sept
East end. Walk to food, beer and downtown fun.
A wide beach with people walking and a few dogs.

16. Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Munjoy Hill
9.6 out of 10, Exceptional, (17 reviews)
"Loved the place! Very eclectic. Easy walk to downtown. Definitely will be back!"
United States
Cameron H.
The price is HK$2,353
HK$4,488 total
includes taxes & fees
15 Sept - 16 Sept
Island View House BnB Self Check-In # 4 / Free Off-Street Parking
A garden with a stone wall, a small pond, and various plants.

17. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is HK$2,829
HK$4,896 total
includes taxes & fees
28 Sept - 29 Sept
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

18. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
The price is HK$2,674
HK$4,009 total
includes taxes & fees
16 Sept - 17 Sept
East End Guesthouse
A deck with wicker furniture and a view of the water.

19. Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is HK$3,725
HK$5,616 total
includes taxes & fees
4 Oct - 5 Oct
Portland’s Best Ocean Views from a 40-Foot Private Deck
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

20. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (9 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is HK$1,561
HK$3,274 total
includes taxes & fees
5 Oct - 6 Oct
NEW 1 BDR-Heart of Munjoy Hill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Diamond Island Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

8/10 Good
"Great location. Close to the waterfront, yet far enough removed to be quiet. Great staff and knowledgeable about food recommendations. My only negative was reception was on the fourth floor. I realize on this trip I enjoy a ground floor lobby seating area and bar in which to congregate. Not the same experience when you ride an elevator up several floors."
David 3-night trip
Posted 2 hours ago
Cambria Hotel Portland Downtown-Old Port

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