A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Great Diamond Island holiday homes

A building named Willard Square with a storefront and a red vehicle parked outside.

1. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is HK$2,810
HK$5,316 total
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

2. 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, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$756
HK$2,886 total
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

3. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (48 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is HK$2,295
HK$3,913 total
includes taxes & fees
18 Oct - 19 Oct
Modern & Sunny House Steps from the Promenade.
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

4. 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, (22 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is HK$3,963
HK$7,133 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

5. 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, (82 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is HK$5,473
HK$8,720 total
includes taxes & fees
19 Oct - 20 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

6. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (16 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is HK$3,249
HK$6,312 total
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

7. 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.
The price is HK$1,726
HK$5,568 total
includes taxes & fees
20 Oct - 21 Oct
Spacious Portland Home + Parking
A two-story brick building with a front porch, a black door, and a window with a white frame.

8. 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 HK$1,695
HK$4,560 total
includes taxes & fees
16 Nov - 17 Nov
The 87th Townhome - Local Landmark
A kitchen with white cabinets, a radiator, and a dining area with a floral chair and a chessboard.

9. Charming West End Victorian

Charming West End Victorian
Parkside
The price is HK$2,197
HK$6,337 total
includes taxes & fees
18 Oct - 19 Oct
Charming West End Victorian
A window with a view of a snowy landscape and bare trees.

10. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is HK$905
HK$2,586 total
includes taxes & fees
18 Oct - 19 Oct
Tranquility between the Lakes & Sea
A living room with a fireplace, leather sofa, and a chandelier.

11. Charming Historic Estate | In-town location

Charming Historic Estate | In-town location
West End
10.0 out of 10, Exceptional, (2 reviews)
"Steve was wonderful and readily available for any of our questions or just helpful recommendations! Made our stay so much more pleasurable!! We enjoyed 3 meals by their on staff chef. She also did an amazing job. We travel with 17 so needless to say it’s a lot but we had more than enough space for everyone. Also, have to mention the outdoor space was delightful!"
United States
shelley w.
The price is HK$12,714
HK$20,727 total
includes taxes & fees
1 Nov - 2 Nov
Charming Historic Estate | In-town location
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

12. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is HK$753
HK$2,724 total
includes taxes & fees
18 Oct - 19 Oct
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

13. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is HK$1,122
HK$3,824 total
includes taxes & fees
19 Oct - 20 Oct
Fully Updated Airy Historic Home in South Freeport
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

14. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is HK$1,369
HK$3,375 total
includes taxes & fees
27 Oct - 28 Oct
Orchid Harbor, Bailey Island 3BR
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

15. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is HK$1,942
HK$4,735 total
includes taxes & fees
25 Oct - 26 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

16. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is HK$3,092
HK$8,117 total
includes taxes & fees
25 Oct - 26 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

17. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is HK$824
HK$1,684 total
includes taxes & fees
1 Nov - 2 Nov
Mid Coast Getaway w/ water views
A lush garden with a hammock, a variety of flowers, and a lake in the background.

18. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is HK$3,453
HK$14,072 total
includes taxes & fees
3 Nov - 4 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A wooden deck with outdoor seating and string lights.

19. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (75 reviews)
"Wonderful stay!"
United States
Erika T.
The price is HK$1,589
HK$2,896 total
includes taxes & fees
27 Oct - 28 Oct
Full sized home
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

20. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is HK$4,061
HK$8,482 total
includes taxes & fees
18 Oct - 19 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
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 Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Nice room comfortable bed. Microwave refrigerator shampoo conditioner soap and lotion. The price was high and the tv didn’t work"
shelley 1-night trip
Posted less than an hour ago
Clarion Pointe South Portland

Find out more about Great Diamond Island

Great Diamond Island Vacation Homes information

Number of reviews
293
Accommodation
591 Vacation Homes
Lowest Price
HK$1,684
Highest Price
HK$20,727

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