Holiday Rentals in Great Diamond Island

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Our top choices for Great Diamond Island holiday rentals

8.4 out of 10, Very good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is €119
includes taxes & fees
9 Jan - 10 Jan
Studio Apartment near downtown Walkable!

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (25)
"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 €161
includes taxes & fees
6 Jan - 7 Jan
Sunny Spot with Private Parking.

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (91)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is €236
includes taxes & fees
16 Jan - 17 Jan
The Weldon Hotel
9.6 out of 10, Exceptional, (128)
"The place was perfect. It was right in the middle of everything and a perfe spot for a getaway"
United States
Jon S.
The price is €162
includes taxes & fees
6 Jan - 7 Jan
Adorable Portland getaway on the Eastern Promenade
2.0 star property
10.0 out of 10, Exceptional, (25)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is €183
includes taxes & fees
6 Jan - 7 Jan
Pine Point Beach private, quaint, charming studio.

Apartment in West Bayside

In-town no frills 2 bedroom apt
8.6 out of 10, Excellent, (17)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is €81
includes taxes & fees
6 Jan - 7 Jan
In-town no frills 2 bedroom apt

Holiday Home in West Point

Escape to Positive Outlook
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is €188
includes taxes & fees
5 Feb - 6 Feb
Escape to Positive Outlook
9.0 out of 10, Wonderful, (27)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
Beautiful 1st Floor Apartment & Amazing Shower
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is €590
includes taxes & fees
6 Jan - 7 Jan
Waterfront Access with Kayaks, Private Deck and a Firepit
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is €235
includes taxes & fees
7 Jan - 8 Jan
Cozy, Elegant and Bright 2 bed in the East End
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 €189
includes taxes & fees
6 Jan - 7 Jan
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
10.0 out of 10, Exceptional, (3)
"Great location to Freeport shopping. Very clean and responsive staff and management. Fun for families with children. We would have liked more room inbetween cabins, but otherwise would highly recommend."
United States
Kathleen K.
The price is €269
includes taxes & fees
11 Jan - 12 Jan
Modern, luxurious cabin in the woods - 19

Holiday Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is €235
includes taxes & fees
9 Jan - 10 Jan
Fantastic Waterfront Views
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is €172
includes taxes & fees
6 Jan - 7 Jan
Peaceful & minutes from the Old Port with private parking

Condo in Old Orchard Beach

350 Yards to the beach. Pet friendly!
8.0 out of 10, Very good, (34)
"Not as nice as some other places we have stayed in OOB, but for the price and closeness to the beach and pier its great. It is right up against the train tracks which wasn’t horrible for us, but could be a significant problem for a light sleeper. "
United States
Kevin S.
The price is €163
includes taxes & fees
19 Jan - 20 Jan
350 Yards to the beach. Pet friendly!
9.8 out of 10, Exceptional, (65)
"Everything was nice & perfectly described. Great quiet neighborhood loved my stay & so did my Dogs thank you for a lovely stay"
United States
Teresa M.
The price is €210
includes taxes & fees
6 Jan - 7 Jan
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is €187
includes taxes & fees
6 Jan - 7 Jan
Charming Studio apartment with WiFi, AC in welcoming Portland

Apartment in Downtown Saco

Saco/Old Orchard Beach Get Away
2.0 star property
10.0 out of 10, Exceptional, (4)
"The host responded quickly and with all the info I could have ever needed. I didn't try the hot tub, but the shower in unit 2 was fantastic. All around very comfortable and clean place that i will go back to."
United States
Paul N.
The price is €332
includes taxes & fees
8 Jan - 9 Jan
Saco/Old Orchard Beach Get Away
2.0 star property
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is €113
includes taxes & fees
18 Jan - 19 Jan
Spacious Studio Near Sebago Lake
9.6 out of 10, Exceptional, (26)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
The price is €178
includes taxes & fees
6 Jan - 7 Jan
Escape to the Beach! Cozy Condo in downtown OOB.
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, apart-hotels, 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 €119 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.