Great Diamond Island Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Great Diamond Island holiday rentals

Private kitchen
The Weldon Hotel

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (89)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is HK$1,435
HK$2,731 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Weldon Hotel
Exterior detail
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
The price is HK$677
HK$1,374 total
includes taxes & fees
14 Dec - 15 Dec
Adorable Portland getaway on the Eastern Promenade
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$539
HK$1,224 total
includes taxes & fees
14 Dec - 15 Dec
Beautiful 1st Floor Apartment & Amazing Shower
Property grounds
Modern, luxurious cabin in the woods - 19

Modern, luxurious cabin in the woods - 19

Modern, luxurious cabin in the woods - 19
Freeport
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 HK$902
HK$1,806 total
includes taxes & fees
15 Dec - 16 Dec
Modern, luxurious cabin in the woods - 19
Smart TV
Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
2.0 star property
Blue Point
10.0 out of 10, Exceptional, (24)
"Sweet place! "
United States
Lisa G.
The price is HK$622
HK$1,552 total
includes taxes & fees
14 Dec - 15 Dec
Pine Point Beach private, quaint, charming studio.
Interior
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"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 HK$724
HK$1,527 total
includes taxes & fees
17 Dec - 18 Dec
Sunny Spot with Private Parking.
Exterior
Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End
Munjoy Hill
9.8 out of 10, Exceptional, (52)
"Excellent stay and location"
United States
David M.
The price is HK$996
HK$2,137 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End
Beach nearby
Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
The price is HK$848
HK$1,543 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cheerful 1 bedroom cottage only 50ft from beach
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt
West Bayside
8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is HK$653
HK$1,212 total
includes taxes & fees
14 Dec - 15 Dec
In-town no frills 2 bedroom apt
Property grounds
Saco/Old Orchard Beach Get Away

Saco/Old Orchard Beach Get Away

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 HK$1,214
HK$2,925 total
includes taxes & fees
13 Dec - 14 Dec
Saco/Old Orchard Beach Get Away
Dining
Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (46)
"Excellent place in every way-- I wish we could have stayed longer!"
United States
Alicia
The price is HK$965
HK$1,789 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming West End Hideaway. Private Parking
Interior
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
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 HK$778
HK$1,687 total
includes taxes & fees
15 Dec - 16 Dec
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Dining
Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (224)
"Outstanding customer service and the view from our loft was incredible. I can’t say enough about how much we enjoyed our stay and we look forward to coming back someday."
United States
Scott M.
The price is HK$2,932
HK$5,096 total
includes taxes & fees
14 Dec - 15 Dec
Downtown Penthouse Suite - Stunning Harbor Views
Fridge, microwave, oven, stovetop
Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (9)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
The price is HK$2,544
HK$4,426 total
includes taxes & fees
4 Jan - 5 Jan 2026
Harborview - Curated East End Escape w/ Parking
Interior
New England Charm, Portland - Parking included

New England Charm, Portland - Parking included

New England Charm, Portland - Parking included
Oakdale
10.0 out of 10, Exceptional, (17)
"Wonderful stay! The place is beautiful, plus it's a great location for walking to coffee shops, running in the park, or a quick trip downtown."
United States
Rachel F.
The price is HK$3,852
HK$6,336 total
includes taxes & fees
31 Dec - 1 Jan 2026
New England Charm, Portland - Parking included
Fridge, microwave, oven, stovetop
Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
Gray
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is HK$1,159
HK$5,424 total
includes taxes & fees
15 Dec - 16 Dec
Waterfront Access with Kayaks, Private Deck and a Firepit
Terrace/patio
Camp Forever cottage

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is HK$1,634
HK$2,824 total
includes taxes & fees
31 Dec - 1 Jan 2026
Camp Forever cottage
Interior
Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is HK$875
HK$1,649 total
includes taxes & fees
13 Dec - 14 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland
Dining
Fall In Love With Portland!

Fall In Love With Portland!

Fall In Love With Portland!
Munjoy Hill
9.6 out of 10, Exceptional, (130)
"Everything was good with our stay. Communication was easy and the place was just as advertised. "
United States
Joe D.
The price is HK$1,237
HK$3,477 total
includes taxes & fees
5 Jan - 6 Jan 2026
Fall In Love With Portland!
Exterior detail
Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (171)
"Great location, clean and cute."
United States
Erin M.
The price is HK$988
HK$1,984 total
includes taxes & fees
14 Dec - 15 Dec
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Perfect room and perfect staff! Excellent on everything "
Conrad 1-night trip
Posted 3 hours ago
Clarion Hotel Portland Airport ME

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