Photo by Robbie Martin

Holiday Homes in Great Diamond Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Great Diamond Island

Our top choices for Great Diamond Island holiday homes

Luxury King Room with Parlor and Balcony

The price is AU$1,034
includes taxes & fees
7 Sept - 8 Sept
Luxury King Room with Parlor and Balcony

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is AU$455
includes taxes & fees
15 Sept - 16 Sept
Camp Forever cottage

Escape to Positive Outlook

The price is AU$479
includes taxes & fees
26 Aug - 27 Aug
Escape to Positive Outlook

Private Entrance Residential Portland

8.8 out of 10, Excellent, (3)
"Check in was simple. Quaint place. "
The price is AU$277
includes taxes & fees
26 Aug - 27 Aug
Private Entrance Residential Portland

Two-story dog-friendly house with enclosed yard, grill, patio, W/D

2.0 star property
9.4 out of 10, Exceptional, (11)
"A clean, beautiful home. It had lots of amenities and space. We had every thing we needed. It felt like home. We will definitely stay there again. "
The price is AU$799
includes taxes & fees
12 Sept - 13 Sept
Two-story dog-friendly house with enclosed yard, grill, patio, W/D

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is AU$401
includes taxes & fees
8 Sept - 9 Sept
Willard Beach–Private Apt Near Portland & Parks

Mid Coast Getaway w/ water views

9.0 out of 10, Wonderful, (2)
"You couldn’t ask for a better view, it was everything we had hoped and more."
The price is AU$439
includes taxes & fees
2 Sept - 3 Sept
Mid Coast Getaway w/ water views

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is AU$729
includes taxes & fees
29 Aug - 30 Aug
Entire Modern Chic Home in Windham

Serenity between the lakes and seashore

9.8 out of 10, Exceptional, (21)
"Good location near lots of hiking and not far from Portland "
The price is AU$550
includes taxes & fees
1 Sept - 2 Sept
Serenity between the lakes and seashore

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (4)
"GoodLocation, very clean. Would stay again "
The price is AU$743
includes taxes & fees
26 Aug - 27 Aug
Luxury on Back Cove - Three Gables

Full sized home

9.8 out of 10, Exceptional, (34)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is AU$565
includes taxes & fees
2 Sept - 3 Sept
Full sized home

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is AU$580
includes taxes & fees
7 Sept - 8 Sept
Sauna & fire table near Portland's Back Cove

Fantastic Waterfront Views

9.8 out of 10, Exceptional, (7)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
The price is AU$786
includes taxes & fees
31 Aug - 1 Sept
Fantastic Waterfront Views

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (3)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
The price is AU$737
includes taxes & fees
24 Sept - 25 Sept
Orchid Harbor, Bailey Island 3BR

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

10.0 out of 10, Exceptional, (4)
"Very clean "
The price is AU$692
includes taxes & fees
24 Sept - 25 Sept
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

10.0 out of 10, Exceptional, (1)
"We had a fantastic stay at this peaceful oceanside property in Harpswell, Maine. The setup—with a main house, attached apartment, and a charming bunkhouse—was perfect for our two families and adult children. There was plenty of space for everyone to relax and unwind.The backyard is absolutely stunning, filled with beautiful flowers and lush grass, and it opens up to a tranquil ocean inlet. We especially loved the hammock spot, perfect for a good book or an afternoon nap, and the back porch...
The price is AU$2,325
includes taxes & fees
1 Sept - 2 Sept
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Bright 3 bedroom located in the heart of OOB

9.0 out of 10, Wonderful, (4)
"The place really was amazing and I would certainly stay again. If I could point out just one pc of advice the floors needed mopping very badly. Thank you for sharing your place with us we made some very special and wonderful memories. "
The price is AU$632
includes taxes & fees
2 Sept - 3 Sept
Bright 3 bedroom located in the heart of OOB

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (1)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
The price is AU$762
includes taxes & fees
26 Aug - 27 Aug
Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

9.6 out of 10, Exceptional, (35)
"This is a great spot to stay no matter what time of the year!! Completely enjoyed my stay!!"
The price is AU$920
includes taxes & fees
26 Aug - 27 Aug
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

Comfortable Motel Room–2 Full Beds, Pool & Parking

10.0 out of 10, Exceptional, (1)
"Great place for us to use as a base as we made our way through Maine!"
The price is AU$266
includes taxes & fees
26 Aug - 27 Aug
Comfortable Motel Room–2 Full Beds, Pool & Parking
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

Find out more about Great Diamond Island

Great Diamond Island Holiday Homes information

Number of reviews
915
Accommodation
572 Holiday Homes
Lowest Price
AU$459
Highest Price
AU$1,383

Explore a world of travel with Expedia

Explore a world of travel with Expedia