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Great Diamond Island Holiday Rentals

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Check prices for these dates

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Great Diamond Island holiday rentals

Property grounds
Modern, Luxurious Cabin in the Woods - 03

Cabin in Freeport

Modern, Luxurious Cabin in the Woods - 03
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is HK$1,315
HK$2,341 total
includes taxes & fees
21 Dec - 22 Dec
Modern, Luxurious Cabin in the Woods - 03
Dining
Escape to Positive Outlook

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 HK$654
HK$1,474 total
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook
Dining
Sunny Spot with Private Parking.

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
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$635
HK$1,413 total
includes taxes & fees
21 Dec - 22 Dec
Sunny Spot with Private Parking.
Outdoor dining
Camp Forever cottage

Holiday Home in Harpswell

Camp Forever cottage
9.6 out of 10, Exceptional, (58)
"Perfect location on the water for a weekend getaway"
United States
Lydia G.
The price is HK$1,471
HK$2,621 total
includes taxes & fees
31 Dec - 1 Jan 2026
Camp Forever cottage
Outdoor dining
Peaceful & minutes from the Old Port with private parking

Apartment in Knightville

Peaceful & minutes from the Old Port with private parking
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 HK$763
HK$1,679 total
includes taxes & fees
11 Jan - 12 Jan 2026
Peaceful & minutes from the Old Port with private parking
TV
Mere Point Sunrise Views at Eastern Shore!

Holiday Home in Brunswick

Mere Point Sunrise Views at Eastern Shore!
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is HK$1,264
HK$3,244 total
includes taxes & fees
21 Dec - 22 Dec
Mere Point Sunrise Views at Eastern Shore!
Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Apartment in Blue Point

Pine Point Beach private, quaint, charming studio.
2.0 star property
10.0 out of 10, Exceptional, (24)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is HK$622
HK$1,552 total
includes taxes & fees
21 Dec - 22 Dec
Pine Point Beach private, quaint, charming studio.
3 bedrooms, WiFi
Fantastic Waterfront Views

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 HK$1,225
HK$2,419 total
includes taxes & fees
11 Jan - 12 Jan 2026
Fantastic Waterfront Views
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

Holiday Home in Freeport

The Outlet Studio, Rustic Comfort w Fireplace
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The Outlet Studio, Rustic Comfort w Fireplace
Living area
The Weldon Hotel

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is HK$1,306
HK$2,591 total
includes taxes & fees
29 Dec - 30 Dec
The Weldon Hotel
Interior
Adorable Portland getaway on the Eastern Promenade

Apartment in Munjoy Hill

Adorable Portland getaway on the Eastern Promenade
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$575
HK$1,263 total
includes taxes & fees
21 Dec - 22 Dec
Adorable Portland getaway on the Eastern Promenade
Exterior
Cheerful 1 bedroom cottage only 50ft from beach

Cottage in Old Orchard Beach

Cheerful 1 bedroom cottage only 50ft from 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$1,518 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cheerful 1 bedroom cottage only 50ft from beach
Beach
Orchid Harbor, Bailey Island 3BR

Holiday Home in Harpswell

Orchid Harbor, Bailey Island 3BR
9.8 out of 10, Exceptional, (7)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is HK$1,433
HK$3,431 total
includes taxes & fees
21 Dec - 22 Dec
Orchid Harbor, Bailey Island 3BR
Exterior
Cozy, Elegant and Bright 2 bed in the East End

Condo in Munjoy Hill

Cozy, Elegant and Bright 2 bed in the East End
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is HK$996
HK$2,146 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End
Beach nearby
Arlie`s Digs! - One Block To Willard Beach!

Condo in Willard Beach

Arlie`s Digs! - One Block To Willard Beach!
10.0 out of 10, Exceptional, (62)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
Arlie`s Digs! - One Block To Willard Beach!
Interior
Waterfront Private Apartment, minutes from LLBean!

Apartment in Freeport

Waterfront Private Apartment, minutes from LLBean!
10.0 out of 10, Exceptional, (16)
"We had a lovely stay at this property. Comfortable bed, beautiful view, enjoyed using the sauna, would stay again."
United States
Emily Jeanne B.
Waterfront Private Apartment, minutes from LLBean!
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Holiday Home in Brunswick

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is HK$1,050
HK$2,901 total
includes taxes & fees
22 Dec - 23 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Interior
City Amenities, Casco Bay Sunrises and Natural Beauty

Condo in East Deering

City Amenities, Casco Bay Sunrises and Natural Beauty
9.8 out of 10, Exceptional, (122)
"The house was clean and homey…everything was well stocked and supplies were even there for our pet…great access to the highway…the views were beautiful…would definitely recommend! "
United States
Michelle M.
The price is HK$840
HK$2,019 total
includes taxes & fees
22 Dec - 23 Dec
City Amenities, Casco Bay Sunrises and Natural Beauty
Private kitchen
Cozy 1-bedroom apartment in lovely Gorham

Apartment in Gorham

Cozy 1-bedroom apartment in lovely Gorham
2.0 star property
The price is HK$498
HK$2,332 total
includes taxes & fees
27 Dec - 28 Dec
Cozy 1-bedroom apartment in lovely Gorham
Property grounds
Welcome to our BoHo Treehouse!

Apartment in Downtown Saco

Welcome to our BoHo Treehouse!
2.0 star property
10.0 out of 10, Exceptional, (8)
"The property was as advertised and very charming for myself and my partner. Checkin and checkout was smooth and easy, and the host was kind enough to let us check out a little later than advertised. Would stay here again."
United States
Benjamin A.
The price is HK$1,012
HK$2,146 total
includes taxes & fees
23 Dec - 24 Dec
Welcome to our BoHo Treehouse!
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Everything! Staff is amazing! I understand you don't have a manager - PLEASE promote Isabella - she's fantastic. I stay here several times a year and it's always excellent!"
Corrine 3-night trip
Posted 3 days ago
Tru by Hilton Portland Airport Area

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