A calm sea with a sailboat and rocky coastline.

Great Diamond Island Holiday Rentals

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Our top choices for Great Diamond Island holiday rentals

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (121 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$755
includes taxes & fees
25 Oct - 26 Oct
The Weldon Hotel

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,239
includes taxes & fees
25 Oct - 26 Oct
Evalina Hotel

3. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is NZ$589
includes taxes & fees
29 Sept - 30 Sept
1/2 Mi to Pier: Wfh-friendly Apt in Maine!

4. Oceanfront Home - Beach Access - Deck + Ping Pong

Oceanfront Home - Beach Access - Deck + Ping Pong
3.5 star property
Old Orchard Beach
The price is NZ$4,707
includes taxes & fees
27 Sept - 28 Sept
Oceanfront Home - Beach Access - Deck + Ping Pong

5. 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$478
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Maine Street! Mcm-style Home in Brunswick

6. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NZ$495
includes taxes & fees
29 Sept - 30 Sept
'beachfront 9' Condo on Old Orchard Beach

7. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is NZ$566
includes taxes & fees
29 Sept - 30 Sept
Walk to Pier & Ocean: Apt in Old Orchard 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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Great Diamond Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Great Diamond Island. 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 Great Diamond Island. 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 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 holiday 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 Great Diamond Island short-term rentals, that won’t be hard to do.

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