Title: Great Diamond Island Vacation Rentals from CA $193: Short-Term Rentals for 2026 | Expedia.ca

[Great Diamond Island Travel Guide](https://expedia.ca/Great-Diamond-Island.dx6342016)[Hotels in Great Diamond Island](https://expedia.ca/Great-Diamond-Island-Hotels.d6342016.Travel-Guide-Hotels)[Flights to Great Diamond Island](https://expedia.ca/Cheap-Flights-To-Great-Diamond-Island.d6342016.Travel-Guide-Flights)[Great Diamond Island Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Diamond-Island.d6342016.Car-Rental-Guide)[Great Diamond Island Vacation Packages](https://expedia.ca/Great-Diamond-Island.d6342016.Destination-Travel-Guides)

![Summer on Casco Bay](https://images.trvl-media.com/place/6342016/fbb7e9ac-5d97-4416-ad7f-d1a6bdfac217.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Great Diamond Island Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Great Diamond Island vacation rentals

![Beach](https://images.trvl-media.com/lodging/121000000/120180000/120177500/120177417/63445671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120180000/120177500/120177417/w1316h847x2y0-34994b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120180000/120177500/120177417/c38e2fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/121000000/120180000/120177500/120177417/6f793f3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Portland

[](https://www.expedia.ca/Portland-Hotels-Cozy-Coveside-Island-Retreat.h120177417.Hotel-Information)

[](https://www.expedia.ca/Portland-Hotels-Cozy-Coveside-Island-Retreat.h120177417.Hotel-Information)

![Deluxe Suite, 1 King Bed | Private kitchen](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/9fd24e5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/6c222be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 King Bed](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/b6c98e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/3eb6def3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Portland

[](https://www.expedia.ca/Portland-Hotels-The-Weldone-Hotel.h107321604.Hotel-Information)

9.8/10

Exceptional

(89)

"Loved this place and would definitely stay here next time we go back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eleni

CA $280

CA $511 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Portland-Hotels-The-Weldone-Hotel.h107321604.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/34000000/33490000/33486400/33486323/cf6e12e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33486400/33486323/337d8564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33490000/33486400/33486323/52bbd800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33486400/33486323/f5021119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Orchard Beach

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Private.h33486323.Hotel-Information)

9.8/10

Exceptional

(45)

"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle N.

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Private.h33486323.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/c81a9afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/bb780683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/c4c02442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/53a78c0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bailey Island

[](https://www.expedia.ca/Bailey-Island-Hotels-New-Cottage-Perfect-For-A-Peaceful-And-Quiet-Stay-On-The-Ocean-With-Beach.h27118287.Hotel-Information)

10/10

Exceptional

(234)

"Tremendous stay, great property and host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Curtis G.

[](https://www.expedia.ca/Bailey-Island-Hotels-New-Cottage-Perfect-For-A-Peaceful-And-Quiet-Stay-On-The-Ocean-With-Beach.h27118287.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/20000000/19260000/19251500/19251469/1dc94df4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/20000000/19260000/19251500/19251469/02ad53d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19260000/19251500/19251469/d3dc4864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19260000/19251500/19251469/5e61ec05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Old Orchard Beach

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Oceanfront-Condo-Steps-To-7-Mile-Beach-Downtown-OOB-3rd-Floor-Welevator.h19251469.Hotel-Information)

9.8/10

Exceptional

(227)

"The view off the deck was breathtaking "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Raymond

CA $241

CA $465 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Oceanfront-Condo-Steps-To-7-Mile-Beach-Downtown-OOB-3rd-Floor-Welevator.h19251469.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/60000000/59870000/59861500/59861453/422fc93c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59870000/59861500/59861453/1e41a71f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59870000/59861500/59861453/95ccdd75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/60000000/59870000/59861500/59861453/6dbcd1ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Orchard Beach

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Sensational-Beachfront-Property-Old-Orchard-Beach.h59861453.Hotel-Information)

9.6/10

Exceptional

(67)

"Great location, clean and the perfect beach front property!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alanna M.

CA $963

CA $1,882 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Sensational-Beachfront-Property-Old-Orchard-Beach.h59861453.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/115000000/114770000/114768500/114768499/b3ca2cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114770000/114768500/114768499/e16b1551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114770000/114768500/114768499/a62b9a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/115000000/114770000/114768500/114768499/cac4d9aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Munjoy Hill

[](https://www.expedia.ca/Portland-Hotels-Charming-Studio-Apartment-With-WiFi.h114768499.Hotel-Information)

9.6/10

Exceptional

(11)

"A great location and a comfortable place to stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrew K.

CA $155

CA $295 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Portland-Hotels-Charming-Studio-Apartment-With-WiFi.h114768499.Hotel-Information)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761466/c3bd41ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761466/31c5f4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761466/91aa5758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761466/dc0b2d57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in West Bayside

[](https://www.expedia.ca/Portland-Hotels-Studio-Unit-Walkable-Everywhere.h114761466.Hotel-Information)

5.8/10

(7)

"We didn't stay there at all. Canceled reservation "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dianne

CA $94

CA $193 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Portland-Hotels-Studio-Unit-Walkable-Everywhere.h114761466.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/24000000/23600000/23591700/23591693/c90968fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23600000/23591700/23591693/54edbd59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23591700/23591693/77ce50ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/24000000/23600000/23591700/23591693/4915ecf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Orchard Beach

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Perfect-For-Families-Friends-Re-Unions-Outdoor-Hot-Tub.h23591693.Hotel-Information)

9.8/10

Exceptional

(97)

"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathleen C.

CA $825

CA $1,713 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Perfect-For-Families-Friends-Re-Unions-Outdoor-Hot-Tub.h23591693.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117730000/117723300/117723273/w1200h798x0y1-96a6ae2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117730000/117723300/117723273/w1199h799x1y1-9e42ddd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117730000/117723300/117723273/w1199h799x1y1-65be81f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117730000/117723300/117723273/w1200h799x0y1-74156d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Old Orchard Beach

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Charming-2-Bedroom-Cottage-In-Peaceful-Old-Orchard-Beach-With-WiFi.h117723273.Hotel-Information)

9.8/10

Exceptional

(12)

"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Natalia R.

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Charming-2-Bedroom-Cottage-In-Peaceful-Old-Orchard-Beach-With-WiFi.h117723273.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/67000000/66470000/66466800/66466792/601abd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/67000000/66470000/66466800/66466792/e9df887a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/67000000/66470000/66466800/66466792/e9e3f968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/67000000/66470000/66466800/66466792/a1b181cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Biddeford

[](https://www.expedia.ca/Portland-Hotels-The-Moonglow-A-Beautiful-Ocean-View-House-In-Biddeford.h66466792.Hotel-Information)

9.8/10

Exceptional

(128)

"Beautiful place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert D.

[](https://www.expedia.ca/Portland-Hotels-The-Moonglow-A-Beautiful-Ocean-View-House-In-Biddeford.h66466792.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761464/d4c429bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761464/ad6007d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761464/7e249362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761464/87d254cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Deering Center

[](https://www.expedia.ca/Portland-Hotels-Private-Entrance-Residential-Portland.h114761464.Hotel-Information)

9.2/10

Wonderful

(5)

"Check in was simple. Quaint place. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle C.

[](https://www.expedia.ca/Portland-Hotels-Private-Entrance-Residential-Portland.h114761464.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/36000000/35790000/35785100/35785044/1e7c0877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35790000/35785100/35785044/abc16b07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/36000000/35790000/35785100/35785044/7048a9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35790000/35785100/35785044/89c24373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Orchard Beach

[](https://www.expedia.ca/Portland-Hotels-Adorable-And-Cozy-1-BR-Cottage-Nestled-In-One-Of-Oobs-Quietest-Neighborhood.h35785044.Hotel-Information)

9.8/10

Exceptional

(65)

"Nice spot to stay with our pup! Chris was available and helpful, and it’s clear he takes care of his property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John and Lori W.

[](https://www.expedia.ca/Portland-Hotels-Adorable-And-Cozy-1-BR-Cottage-Nestled-In-One-Of-Oobs-Quietest-Neighborhood.h35785044.Hotel-Information)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90330000/90322600/90322528/ba44aac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90330000/90322600/90322528/7454ecba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90330000/90322600/90322528/dd85f9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90330000/90322600/90322528/0675ac78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Long Island

[](https://www.expedia.ca/Long-Island-Hotels-Updated-Long-Island-Maine-Cottage.h90322528.Hotel-Information)

10/10

Exceptional

(7)

"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Serra C.

[](https://www.expedia.ca/Long-Island-Hotels-Updated-Long-Island-Maine-Cottage.h90322528.Hotel-Information)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/30000000/29630000/29624500/29624474/0881cf66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29630000/29624500/29624474/4dab1a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29630000/29624500/29624474/a07fbd94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29630000/29624500/29624474/b0afa947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Freeeport

[](https://www.expedia.ca/Portland-Hotels-New-Well-Built-Elegant-Home-On-The-Water-2-Miles-To-Freeport.h29624474.Hotel-Information)

9.8/10

Exceptional

(197)

"My family had a wonderful time! The house was perfect for us. It was comfy and so well equipped.The location was absolutely perfect. The neighborhood was quiet and friendly. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maryann A.

[](https://www.expedia.ca/Portland-Hotels-New-Well-Built-Elegant-Home-On-The-Water-2-Miles-To-Freeport.h29624474.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116140000/116131600/116131538/a5f6ac3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116140000/116131600/116131538/6d334cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116140000/116131600/116131538/860ab508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116140000/116131600/116131538/c55be1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Falmouth

[](https://www.expedia.ca/Falmouth-Hotels-Charming-2-Bedroom-House-With-AC.h116131538.Hotel-Information)

8.8/10

Excellent

(6)

"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Darcie B.

[](https://www.expedia.ca/Falmouth-Hotels-Charming-2-Bedroom-House-With-AC.h116131538.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42510000/42503700/42503640/1ca5ad86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42510000/42503700/42503640/3fe30255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/43000000/42510000/42503700/42503640/2b50fd83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42510000/42503700/42503640/eccaabd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Old Orchard Beach

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Spectacular-Beachfront-Condo-Watch-Sunrise-From-Deck-Overlooking-Beach.h42503640.Hotel-Information)

9.8/10

Exceptional

(36)

"Great spot...everything was great "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Frank R.

[](https://www.expedia.ca/Old-Orchard-Beach-Hotels-Spectacular-Beachfront-Condo-Watch-Sunrise-From-Deck-Overlooking-Beach.h42503640.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27120000/27116800/27116751/f039aeac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27120000/27116800/27116751/dad3f43f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27116800/27116751/02437bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27116800/27116751/88839240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Harpswell

[](https://www.expedia.ca/Harpswell-Hotels-1-Room-Luxury-Ocean-Front-Studio-Cottage.h27116751.Hotel-Information)

9.6/10

Exceptional

(171)

"Very clean beautiful view we definitely enjoyed ourselves "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ilona F.

[](https://www.expedia.ca/Harpswell-Hotels-1-Room-Luxury-Ocean-Front-Studio-Cottage.h27116751.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/69000000/68150000/68148900/68148849/fa49db0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68150000/68148900/68148849/4df0a352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68150000/68148900/68148849/bc2242b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/69000000/68150000/68148900/68148849/2c4df6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Portland

[](https://www.expedia.ca/Portland-Hotels-Back-Yard-Paradise.h68148849.Hotel-Information)

9.8/10

Exceptional

(22)

"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justin J.

[](https://www.expedia.ca/Portland-Hotels-Back-Yard-Paradise.h68148849.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/20000000/19410000/19403100/19403008/8f0b4588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 Double Bed (#11) | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19410000/19403100/19403008/884e3094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms (#173)](https://images.trvl-media.com/lodging/20000000/19410000/19403100/19403008/d305235c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 3 Bedrooms (#173) | Living area](https://images.trvl-media.com/lodging/20000000/19410000/19403100/19403008/9932cb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Surfside

[](https://www.expedia.ca/Portland-Hotels-Little-Miss-Cottages.h19403008.Hotel-Information)

8.4/10

Very good

(88)

"Cute and tidy cottage, easy walk to beautiful beach."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charlotte

[](https://www.expedia.ca/Portland-Hotels-Little-Miss-Cottages.h19403008.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-29&endDate=2025-12-30&regionId=6342016&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Great+Diamond+Island%2C+Maine%2C+United+States+of+America&regionId=6342016&latLong=43.679165%2C-70.197243&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APART_HOTEL)

Apartments

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Great+Diamond+Island%2C+Maine%2C+United+States+of+America&regionId=6342016&latLong=43.679165%2C-70.197243&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Great+Diamond+Island%2C+Maine%2C+United+States+of+America&regionId=6342016&latLong=43.679165%2C-70.197243&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Great+Diamond+Island%2C+Maine%2C+United+States+of+America&regionId=6342016&latLong=43.679165%2C-70.197243&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Great+Diamond+Island%2C+Maine%2C+United+States+of+America&regionId=6342016&latLong=43.679165%2C-70.197243&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VACATION_HOME)

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## Top Great Diamond Island Hotel Reviews

![Aloft Portland Downtown Waterfront ME](https://images.trvl-media.com/lodging/69000000/68850000/68847400/68847370/b64a7749_y.jpg)

### Aloft Portland Downtown Waterfront ME

10/10 Excellent

"Clean room, fun design, very quiet "

[](https://expedia.ca/Portland-Hotels-Aloft-Portland.h68847370.Hotel-Information)

![Holiday Inn Portland-By the Bay by IHG](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/e922ee9f_y.jpg)

### Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"Every thing was perfect, service, accomodations, and friendly staff!!!"

[](https://expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information)

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg)

### Clarion Hotel Portland Airport ME

10/10 Excellent

"Perfect room and perfect staff! Excellent on everything "

[](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information)

![Hyatt Place Portland Downtown - Old Port Square](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/b4e33349_y.jpg)

### Hyatt Place Portland Downtown - Old Port Square

10/10 Excellent

"The only thing I would change is your handicap rooms are very far from the elevator"

[](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information)

![Canopy by Hilton Portland Waterfront](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/419cdab1_y.jpg)

### Canopy by Hilton Portland Waterfront

10/10 Excellent

"Great location. Clean rooms. Good restaurants with Ken walking distance."

[](https://expedia.ca/Portland-Hotels-Canopy-By-Hilton-Portland-Waterfront.h64474828.Hotel-Information)

![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/33bb60f2_y.jpg)

### DoubleTree by Hilton Hotel Portland

10/10 Excellent

"Clean rooms and friendly staff! About a 10-15 min drive from downtown Portland."

[](https://expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information)

![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg)

### Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"clean room, digital key wonderful, good breakfast selection, staff very accommodating. Pool water very, very cloudy (negative)"

[](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information)

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg)

### Portland Harbor Hotel

10/10 Excellent

"Everything was great! However it would nivce if there was a microwave at the snack stations on each floor."

[](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information)

![Fireside Inn & Suites Portland](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/bc09b846_y.jpg)

### Fireside Inn & Suites Portland

10/10 Excellent

"The room was clean"

[](https://expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information)

## Find out more about Great Diamond Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Great Diamond Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Great Diamond Island ](https://expedia.ca/Great-Diamond-Island-Private-Vacation-Homes.d6342016-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Condo Rentals in Great Diamond Island ](https://expedia.ca/Great-Diamond-Island-Condos.d6342016-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Great Diamond Island ](https://expedia.ca/Great-Diamond-Island-Cottages.d6342016-aaCottages.Travel-Guide-Accommodation)
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- [B&B in Great Diamond Island ](https://expedia.ca/Great-Diamond-Island-Bed-And-Breakfast.d6342016-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Great Diamond Island ](https://expedia.ca/Great-Diamond-Island-Apart-Hotels.d6342016-aaApartHotels.Travel-Guide-Accommodation)
- [Farmstay in Great Diamond Island ](https://expedia.ca/Great-Diamond-Island-Agritourism.d6342016-aaAgritourism.Travel-Guide-Accommodation)
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