Photo by Robbie Martin

Great Diamond Island Holiday Rentals

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Holiday Rentals in Great Diamond Island

Escape to Positive Outlook

West Point
10.0 out of 10, Exceptional, (2)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is NZ$385
includes taxes & fees
1 Dec - 2 Dec
Escape to Positive Outlook

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 NZ$413
includes taxes & fees
2 Dec - 3 Dec
Modern, Luxurious Cabin in the Woods - 03

Fantastic Waterfront Views

West Point
9.8 out of 10, Exceptional, (12)
"The place is amazing with lots of room for a family, and great views of the water from almost everywhere. The neighborhood is quiet and the people were very friendly. "
United States
Joseph V.
The price is NZ$482
includes taxes & fees
3 Dec - 4 Dec
Fantastic Waterfront Views

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Harpswell
10.0 out of 10, Exceptional, (4)
"Beautiful location!! Very comfortable and clean home "
United States
Beth L.
The price is NZ$1,006
includes taxes & fees
10 Nov - 11 Nov
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
The price is NZ$351
includes taxes & fees
12 Nov - 13 Nov
Sunny Spot with Private Parking.

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is NZ$471
includes taxes & fees
11 Nov - 12 Nov
Brunswick Downtown Sugar Cube next to Bowdoin

Centerview cottage

Harpswell
9.6 out of 10, Exceptional, (59)
"Had a great stay at the Centerview cottage! Views were spectacular, saw lots of wildlife right from the deck. We enjoyed paddling around the area with the kayaks and jumping in for a quick dunk from the dock. Can’t wait to come back next summer."
United States
Jennifer O.
The price is NZ$669
includes taxes & fees
1 Dec - 2 Dec
Centerview cottage

Camp Forever cottage

Harpswell
9.6 out of 10, Exceptional, (57)
"Nice, quiet location. Bed is super comfortable, and everything is neat and clean inside. We were a little confused which kayaks we could use and how to get them down to the water, and we were encouraged to use life vests, but there were none available (and we did not bring any with us). Otherwise, hosts were very responsive and we had a nice time."
United States
Lisa K.
The price is NZ$688
includes taxes & fees
30 Nov - 1 Dec
Camp Forever cottage

Peaceful & minutes from the Old Port with private parking

Knightville
9.8 out of 10, Exceptional, (7)
"My husband and I had a wonderful weekend in South Portland and enjoyed the central location and charming touches of Jennifer’s apartment. The space is lovely, exactly as described in the listing. The communication was clear and detailed. We will definitely return!"
United States
Caitlin C.
The price is NZ$384
includes taxes & fees
11 Nov - 12 Nov
Peaceful & minutes from the Old Port with private parking

Saco/Old Orchard Beach Get Away

2.0 star property
Saco
10.0 out of 10, Exceptional, (3)
"the apartment was perfect! It was clean and comfortable. Bed and pillows were great. Walking distance to some really sweet coffe shops. We fell in love with Swell! Thank you for being so patient with us as navigated some excited kids after long days of playing lacrosse! Great hosts!! "
United States
Jessica L.
The price is NZ$644
includes taxes & fees
10 Nov - 11 Nov
Saco/Old Orchard Beach Get Away

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brunswick
9.8 out of 10, Exceptional, (27)
" Very spacious, clean and beautiful."
United States
robert p.
The price is NZ$589
includes taxes & fees
10 Nov - 11 Nov
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (23)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
The price is NZ$605
includes taxes & fees
29 Nov - 30 Nov
Serenity between the lakes and seashore

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Saco
10.0 out of 10, Exceptional, (13)
"perfect for a couple wanting something that is clean and cozy near beaches in Maine"
United States
Karalyn K.
The price is NZ$538
includes taxes & fees
13 Nov - 14 Nov
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

Old Orchard Beach
7.2 out of 10, Good, (12)
"The property is charmless. Not clean. Linens and towels are disgusting. Very disappointed. Especially for the price I paid."
United States
Darla J.
The price is NZ$345
includes taxes & fees
11 Nov - 12 Nov
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

Waterfront Private Apartment, minutes from LLBean!

Freeport
10.0 out of 10, Exceptional, (15)
"We had a lovely stay at this property. Comfortable bed, beautiful view, enjoyed using the sauna, would stay again."
United States
Emily Jeanne B.
The price is NZ$282
includes taxes & fees
10 Nov - 11 Nov
Waterfront Private Apartment, minutes from LLBean!

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is NZ$337
includes taxes & fees
16 Nov - 17 Nov
Adorable Portland getaway on the Eastern Promenade

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

Brunswick
8.8 out of 10, Excellent, (21)
"Great location for baileys island and popham"
United States
Anonymous traveller
The price is NZ$711
includes taxes & fees
16 Nov - 17 Nov
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill
9.8 out of 10, Exceptional, (169)
"Lots of room, great neighborhood, easy entry"
United States
Joel F.
The price is NZ$504
includes taxes & fees
1 Dec - 2 Dec
Glorious getaway on Portland's Eastern Promenade.

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is NZ$491
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

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

Willard Beach
10.0 out of 10, Exceptional, (60)
"Near beach, walking, bakery, ice cream and close to great restaurants. Lovely spot and easily accommodated 2 couples. Would stay here again!"
United States
Kirstin D.
The price is NZ$676
includes taxes & fees
11 Nov - 12 Nov
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 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$249 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.