A calm sea with a sailboat and rocky coastline.

Holiday Homes in Great Diamond Island

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Our top choices for Great Diamond Island holiday homes

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 AU$551
includes taxes & fees
19 Oct - 20 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

2. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 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 AU$422
includes taxes & fees
22 Sept - 23 Sept
Serenity between the lakes and seashore

3. 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, (108 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AU$929
includes taxes & fees
22 Sept - 23 Sept
The Globe House on Munjoy Hill - Walk to Breweries

4. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 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 AU$820
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home

5. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$820
includes taxes & fees
27 Sept - 28 Sept
Modern & Sunny House Steps from the Promenade.

6. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AU$484
includes taxes & fees
28 Sept - 29 Sept
Tranquility between the Lakes & Sea

7. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AU$560
includes taxes & fees
22 Sept - 23 Sept
Quiet Spot in lovely Freeport neighborhood

8. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is AU$713
includes taxes & fees
23 Sept - 24 Sept
Fully Updated Airy Historic Home in South Freeport

9. 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, (15 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
Rare West End Home • Walk to Old Port, Harbor View

10. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AU$516
includes taxes & fees
22 Sept - 23 Sept
Full sized home

11. 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, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is AU$1,544
includes taxes & fees
22 Sept - 23 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

12. 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 AU$1,101
includes taxes & fees
27 Sept - 28 Sept
The 87th Townhome - Local Landmark

13. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is AU$893
includes taxes & fees
22 Sept - 23 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

14. SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is AU$1,292
includes taxes & fees
24 Sept - 25 Sept
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

15. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 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 AU$309
includes taxes & fees
28 Sept - 29 Sept
Mid Coast Getaway w/ water views

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

17. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$510
includes taxes & fees
23 Sept - 24 Sept
Camp Forever cottage

18. 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, (3 reviews)
"The property was beautifully decorated, cleaned to perfection, and a great size home for our family trip. Thank you Mike and Kate!"
United States
Gina H.
The price is AU$1,775
includes taxes & fees
1 Oct - 2 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC

19. ⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
Old Orchard Beach
10.0 out of 10, Exceptional, (9 reviews)
"This house was perfect."
United States
Courtney S.
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
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

Find out more about Great Diamond Island

Great Diamond Island Holiday Homes information

Number of reviews
545
Accommodation
597 Holiday Homes
Lowest Price
AU$309
Highest Price
AU$1,775

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