Summer on Casco Bay

Great Diamond Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Great Diamond Island holiday rentals

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 NZ$635
includes taxes & fees
6 July - 7 July
The Weldon Hotel

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is NZ$641
includes taxes & fees
28 June - 29 June
Modern, Luxurious Cabin in the Woods - 03

'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is NZ$1,116
includes taxes & fees
19 July - 20 July
'osprey Cottage' South Freeport Home on Casco Bay!

Cozy Newly Renovated 2-bedroom Condo By The Beach

Cozy Newly Renovated 2-bedroom Condo By The Beach
Saco
9.6 out of 10, Exceptional, (4 reviews)
"Clean, allowed us to check in earlier, Accommodating host. Convenient location Would stay again "
United States
Carlos P.
The price is NZ$703
includes taxes & fees
28 June - 29 June
Cozy Newly Renovated 2-bedroom Condo By The Beach

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is NZ$747
includes taxes & fees
29 June - 30 June
Large, luxurious geodesic dome - 04

New Listing! AmongstTheAspens - Off-Grid Tiny Home

New Listing! AmongstTheAspens - Off-Grid Tiny Home
Saco
9.2 out of 10, Wonderful, (15 reviews)
"Had a great stay, very private property. House was very clean and user friendly. Would definitely stay again, thanks"
United States
Doug C.
The price is NZ$609
includes taxes & fees
6 July - 7 July
New Listing! AmongstTheAspens - Off-Grid Tiny Home

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is NZ$692
includes taxes & fees
2 July - 3 July
Fortland Island Campground

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$644
includes taxes & fees
1 July - 2 July
Full sized home

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (62 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is NZ$832
includes taxes & fees
28 June - 29 June
Centerview cottage

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
Old Orchard Beach
10.0 out of 10, Exceptional, (8 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful place!"
United States
Louise P.
Nautical View

'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is NZ$1,106
includes taxes & fees
19 July - 20 July
'Osprey Cottage' South Freeport Home on Casco Bay!

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is NZ$581
includes taxes & fees
16 July - 17 July
1 Mi to Maine Street! Mcm-style Home in Brunswick

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco
Saco
9.6 out of 10, Exceptional, (5 reviews)
"The coastal condo was comfortable and a great place to stay! "
United States
Tara P.
The price is NZ$755
includes taxes & fees
30 June - 1 July
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (47 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
The price is NZ$809
includes taxes & fees
21 July - 22 July
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is NZ$1,123
includes taxes & fees
2 July - 3 July
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (32 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is NZ$485
includes taxes & fees
28 June - 29 June
Pine Point Beach private, quaint, charming studio.

Upscale Spacious OOB Beach House - Seasonal Heated Pool

Upscale Spacious OOB Beach House - Seasonal Heated Pool
Old Orchard Beach
10.0 out of 10, Exceptional, (15 reviews)
"The place was great, lot's of room for everyone. It was easy to drive around to where we were going. We would definitely recommend this place. "
United States
Robin T.
The price is NZ$943
includes taxes & fees
1 July - 2 July
Upscale Spacious OOB Beach House - Seasonal Heated Pool

The Links Lodge - Modern Golf and Beach Retreat

The Links Lodge - Modern Golf and Beach Retreat
Old Orchard Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great home for family!"
United States
Christie B.
The price is NZ$1,658
includes taxes & fees
30 June - 1 July
The Links Lodge - Modern Golf and Beach Retreat

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (129 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 NZ$837
includes taxes & fees
29 June - 30 June
City Amenities, Casco Bay Sunrises and Natural Beauty
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Great Diamond Island Hotel Reviews

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Diamond Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Great Diamond Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Diamond Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Diamond Island holiday rentals we have selected for you start as low as NZ$398 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Diamond Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Diamond Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Diamond Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia