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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Great Diamond Island holiday rentals

A dining table with chairs, a potted plant, and decorative items.

1. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is £262
includes taxes & fees
21 Oct - 22 Oct
Willard Beach–Apartment Near Portland & Parks
A street lined with buildings, one with a red door and a sign that reads "MINATO".

2. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (153 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is £222
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

3. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is £178
includes taxes & fees
1 Nov - 2 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

4. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is £76
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A multi-story building with a stone facade, large windows, and a corner entrance.

5. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is £370
includes taxes & fees
3 Nov - 4 Nov
Evalina Hotel
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

6. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"We had a great stay in Portland! The place was just as described and the hosts were easy to communicate with. A good place for a couple nights within walking distance of all Portland has to offer."
United States
Lucy T.
The price is £117
includes taxes & fees
1 Nov - 2 Nov
Studio Apartment near downtown Walkable!
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

7. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (125 reviews)
"Really nice room and location"
United States
Victoria
The price is £222
includes taxes & fees
2 Nov - 3 Nov
The Weldon Hotel
A modern house with a wooden exterior, a small garden, and a visible window.

8. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is £354
includes taxes & fees
18 Oct - 19 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

9. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (36 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is £225
includes taxes & fees
12 Oct - 13 Oct
Sunny Spot with Private Parking.
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

10. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is £87
includes taxes & fees
13 Oct - 14 Oct
Portland 1-bedroom with enclosed porch & parking
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is £346
includes taxes & fees
2 Nov - 3 Nov
Arlie`s Digs! - One Block To Willard Beach!
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

12. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (85 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
The price is £386
includes taxes & fees
12 Oct - 13 Oct
Elegant condo - walk to Portland's best restaurants & Old Port
A living room with a sofa, armchairs, a coffee table, and a potted plant.

13. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is £135
includes taxes & fees
4 Nov - 5 Nov
Beautiful 1st Floor Apartment & Amazing Shower
Exterior

14. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (114 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is £344
includes taxes & fees
19 Oct - 20 Oct
Ocean View East End Studio in a Historic Victorian
A black console table with a mirror above it, a lamp, and a potted plant beside it.

15. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is £255
includes taxes & fees
1 Nov - 2 Nov
Peaceful & minutes from the Old Port with private parking
A coastal view with a house, a tree, and a beach.

16. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
The price is £452
includes taxes & fees
9 Nov - 10 Nov
Willard By the Sea - 30 ft to the beach- 2nd floor
A house with a wooden staircase leading to a door marked with the number 50.

17. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (107 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is £201
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

18. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic little spot. Great location and easy to find parking even if not using what is reserve. Home had everything necessary for a stay. Hosts were prompt with communication."
United States
Susan
The price is £311
includes taxes & fees
20 Oct - 21 Oct
NEW 1 BDR-Heart of Munjoy Hill
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is £300
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A street lined with buildings, one with a red door and a sign that reads "MINATO".

20. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (188 reviews)
"The property is well equipped for a long weekend. Parking was convenient. The location offered a quiet place to stay just minutes from Portland’s bustling commercial corridors. Will definitely look to book again on our next visit."
United States
William
The price is £354
includes taxes & fees
14 Oct - 15 Oct
Glorious getaway on Portland's Eastern Promenade.
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"An hour after we were in our room, clerk asked us if we minded to move, that he gave us the wrong room! Believe it! We didn’t move. I asked for the only burned out light to be replaced above the sink, and was told it was on order! When I asked the night clerk for keurig coffee cups he brought me a tea. When he returned with cream and sugar packets, I gave him the unneeded tea. He dropped it into my paper coffee cup! Believe it! The small parking lot can be a trap so be careful. But it was a good price in pricey Portland."
Jim 1-night trip
Posted less than an hour ago
Inn at St John Portland In-Town

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 £114 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. 

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