A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Great Diamond Island vacation homes

Interior

1. 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 AED 386
AED 1,397 total
includes taxes & fees
3 Sep - 4 Sep
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Smart TV

2. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (5 reviews)
"I loved spending time in this thoughtfully put together home. It is indeed chic, very personal, and our cat was comfortable here. The downstairs shower was my favorite bathroom, the shower is beautiful and cozy. The beds are wonderfully comfortable, and there were featherdown pillows in each room. My kids did argue over who got the small cute though "
United States
Penelope L.
The price is AED 1,197
AED 2,154 total
includes taxes & fees
30 Aug - 31 Aug
Chic 3-bedroom house in Munjoy Hill with off-street parking.
Outdoor dining

3. Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is AED 1,315
AED 2,142 total
includes taxes & fees
1 Sep - 2 Sep
Modern & Sunny House Steps from the Promenade. Private Parking!
Property grounds

4. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (29 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is AED 547
AED 1,277 total
includes taxes & fees
7 Sep - 8 Sep
Serenity between the lakes and seashore
Exterior

5. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is AED 1,102
AED 2,220 total
includes taxes & fees
30 Aug - 31 Aug
Willard Square Family Home
Outdoor dining

6. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (103 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AED 1,175
AED 2,198 total
includes taxes & fees
15 Sep - 16 Sep
The Globe House on Munjoy Hill - Walk to Breweries
TV, offices

7. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is AED 790
AED 2,130 total
includes taxes & fees
27 Aug - 28 Aug
Fully Updated Airy Historic Home in South Freeport
Interior

8. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 830
AED 1,722 total
includes taxes & fees
23 Sep - 24 Sep
Tranquility between the Lakes & Sea
Exterior

9. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.4 out of 10, Exceptional, (9 reviews)
"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"
United States
Amy B.
The price is AED 1,158
AED 2,568 total
includes taxes & fees
31 Aug - 1 Sep
The 87th Townhome - Local Landmark
TV, fireplace

10. Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View
West End
9.8 out of 10, Exceptional, (14 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
Rare West End Home • Walk to Old Port, Harbor View
TV, fireplace, books

11. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (11 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is AED 242
AED 1,021 total
includes taxes & fees
23 Sep - 24 Sep
1 Mi to Maine Street! MCM-Style Home in Brunswick
Outdoor dining

12. Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.6 out of 10, Excellent, (4 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
Spacious Portland Home + Parking
Interior

13. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (17 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
Spacious 4-bedroom house located in the heart of Portland, ME.
Terrace/patio

14. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (66 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AED 826
AED 1,465 total
includes taxes & fees
22 Sep - 23 Sep
Full sized home
Exterior detail

15. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (79 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is AED 3,438
AED 5,016 total
includes taxes & fees
23 Sep - 24 Sep
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Coffee/tea maker, fridge, microwave, dishwasher

16. Quiet Spot in Lovely Freeport Neighborhood

Quiet Spot in Lovely Freeport Neighborhood
Freeport
The price is AED 757
AED 1,788 total
includes taxes & fees
8 Sep - 9 Sep
Quiet Spot in Lovely Freeport Neighborhood
Interior

17. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Oakdale
10.0 out of 10, Exceptional, (1 review)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
United States
Andy W.
The price is AED 2,314
AED 5,321 total
includes taxes & fees
15 Sep - 16 Sep
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
TV, offices

18. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is AED 702
AED 2,658 total
includes taxes & fees
9 Sep - 10 Sep
Windham Lakefront: Fire Pit and Modern Comforts
TV

19. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AED 579
AED 1,042 total
includes taxes & fees
1 Sep - 2 Sep
Mid Coast Getaway w/ water views
Terrace/patio

20. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AED 771
AED 1,349 total
includes taxes & fees
30 Aug - 31 Aug
Camp Forever cottage
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

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent
"Great location, nice and new property well maintained. Rooms are spacious, we had a 2 queen bed room for our family and had plenty of space. The wooden floors add a nice touch to room. Very walkable location close to restaurants and cafes. There is a brewery downstairs where you get discounts if staying here, All in all great experience."
Prabhjot Singh 1-night trip
Posted less than an hour ago
Cambria Hotel Portland Downtown-Old Port

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