Great Diamond Island Holiday Rentals

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Holiday Rentals in Great Diamond Island

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"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 AU$360
includes taxes & fees
16 Dec - 17 Dec
Modern, Luxurious Cabin in the Woods - 03

The Outlet House, Comfortable Cottage

Freeport
9.8 out of 10, Exceptional, (49)
"Fantastic house in a great location! Will definitely be back"
United States
Brandon G.
The price is AU$327
includes taxes & fees
7 Dec - 8 Dec
The Outlet House, Comfortable Cottage

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is AU$303
includes taxes & fees
7 Dec - 8 Dec
Sunny Spot with Private Parking.

Camp Forever cottage

Harpswell
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is AU$561
includes taxes & fees
31 Dec - 1 Jan 2026
Camp Forever cottage

Mere Point Sunrise Views at Eastern Shore!

Brunswick
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
Mere Point Sunrise Views at Eastern Shore!

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (14)
"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. "
United States
Heather S.
The price is AU$475
includes taxes & fees
26 Dec - 27 Dec
Fantastic Waterfront Views

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
The price is AU$245
includes taxes & fees
4 Dec - 5 Dec
The Outlet Studio, Rustic Comfort w Fireplace

Peaceful & minutes from the Old Port with private parking

Knightville
9.8 out of 10, Exceptional, (7)
"Super Cute little apartment! My only complaint, is the parking. It gets a little tight. And the bed is a little firm for my liking, but overall it was super nice and convenient!"
United States
Samantha
The price is AU$300
includes taxes & fees
4 Dec - 5 Dec
Peaceful & minutes from the Old Port with private parking

Pine Point Beach private, quaint, charming studio.

2.0 star property
Scarborough
10.0 out of 10, Exceptional, (24)
"Sweet place! "
United States
Lisa G.
The price is AU$354
includes taxes & fees
16 Dec - 17 Dec
Pine Point Beach private, quaint, charming studio.

Welcome to our BoHo Treehouse!

2.0 star property
Saco
10.0 out of 10, Exceptional, (8)
"Was blown away by the charm, decor and how welcoming the property was. Peaceful, quiet, clean. Will be returning at some point in the future!"
United States
Robert H.
The price is AU$387
includes taxes & fees
15 Dec - 16 Dec
Welcome to our BoHo Treehouse!

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (127)
"So clean! Loved all the little notes, very helpful. Such a great location close to the water and would definitely recommend this place in the future."
United States
Lorena
The price is AU$251
includes taxes & fees
4 Dec - 5 Dec
Adorable Portland getaway on the Eastern Promenade

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$328
includes taxes & fees
4 Dec - 5 Dec
The Weldon Hotel

Spacious Studio Near Sebago Lake

2.0 star property
Windham
10.0 out of 10, Exceptional, (1)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is AU$190
includes taxes & fees
5 Dec - 6 Dec
Spacious Studio Near Sebago Lake

Beautiful 1st Floor Apartment & Amazing Shower

Parkside
9.0 out of 10, Wonderful, (26)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is AU$244
includes taxes & fees
16 Dec - 17 Dec
Beautiful 1st Floor Apartment & Amazing Shower

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick
8.8 out of 10, Excellent, (23)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is AU$613
includes taxes & fees
16 Dec - 17 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Cheerful 1 bedroom cottage only 50ft from beach

Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
The price is AU$379
includes taxes & fees
16 Dec - 17 Dec
Cheerful 1 bedroom cottage only 50ft from beach

City Amenities, Casco Bay Sunrises and Natural Beauty

East Deering
9.8 out of 10, Exceptional, (122)
"I loved staying in the vacation rental! There was a lot of space, a nice waterfront view, and it was convenient to get in/out of town. "
United States
Jade G.
The price is AU$474
includes taxes & fees
16 Dec - 17 Dec
City Amenities, Casco Bay Sunrises and Natural Beauty

Charming Studio apartment with WiFi, AC in welcoming Portland

Munjoy Hill
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is AU$327
includes taxes & fees
5 Dec - 6 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Old Orchard Beach
8.0 out of 10, Very good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is AU$332
includes taxes & fees
16 Dec - 17 Dec
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

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

Willard Beach
10.0 out of 10, Exceptional, (61)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is AU$476
includes taxes & fees
9 Dec - 10 Dec
Arlie`s Digs! - One Block To Willard Beach!
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

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 favourite 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 depend 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 AU$216 per night. Entering your travel dates in the search wizard might find you 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.