A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Great Diamond Island vacation homes

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

1. 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 ￥118,360
￥185,597 total
includes taxes & fees
Sep 23 - Sep 24
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A two-story house with a balcony, a covered patio, and a fenced yard.

2. 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 ￥58,202
￥103,796 total
includes taxes & fees
Oct 6 - Oct 7
The Globe House on Munjoy Hill - Walk to Breweries
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

3. 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, (20 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is ￥91,712
￥158,265 total
includes taxes & fees
Oct 20 - Oct 21
Spacious 4-bedroom house located in the heart of Portland, ME.
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

4. 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 ￥53,967
￥87,552 total
includes taxes & fees
Oct 5 - Oct 6
Modern & Sunny House Steps from the Promenade.
A living room with a fireplace, leather sofa, and a chandelier.

5. 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 ￥271,089
￥435,364 total
includes taxes & fees
Oct 6 - Oct 7
Charming Historic Estate | In-town location
A building named Willard Square with a storefront and a red vehicle parked outside.

6. 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 ￥47,193
￥95,077 total
includes taxes & fees
Oct 14 - Oct 15
Willard Square Family Home
A living room with a sofa, a coffee table, and a vase on a windowsill.

7. 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.
The price is ￥43,346
￥91,878 total
includes taxes & fees
Sep 24 - Sep 25
Rare West End Home • Walk to Old Port, Harbor View
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 ￥53,347
￥113,018 total
includes taxes & fees
Sep 28 - Sep 29
The 87th Townhome - Local Landmark
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

9. 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 ￥34,514
￥110,979 total
includes taxes & fees
Sep 27 - Sep 28
Spacious Portland Home + Parking
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

10. 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 ￥18,614
￥62,013 total
includes taxes & fees
Oct 19 - Oct 20
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

11. 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 ￥49,417
￥108,413 total
includes taxes & fees
Oct 1 - Oct 2
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A house with a porch, an American flag, and a full moon in the sky.

12. Large Groups! Pine Point Beach 8 BDRM!

Large Groups! Pine Point Beach 8 BDRM!
Pine Point
10.0 out of 10, Exceptional, (8 reviews)
"The location is excellent. The house is great for a large family; everyone can have a sleeping space and privacy."
United States
Susan K.
The price is ￥137,270
￥245,784 total
includes taxes & fees
Sep 27 - Sep 28
Large Groups! Pine Point Beach 8 BDRM!
A window with a view of a snowy landscape and bare trees.

13. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is ￥17,947
￥51,027 total
includes taxes & fees
Sep 27 - Sep 28
Tranquility between the Lakes & Sea
A modern living room with a large sofa set, a coffee table, and a view of the ocean through large windows.

14. Oceanfront Home - Beach Access - Deck + Ping Pong

Oceanfront Home - Beach Access - Deck + Ping Pong
3.5 star property
Old Orchard Beach
The price is ￥160,771
￥429,142 total
includes taxes & fees
Sep 24 - Sep 25
Oceanfront Home - Beach Access - Deck + Ping Pong
A dirt path in a park with autumn foliage.

15. 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 ￥69,043
￥98,684 total
includes taxes & fees
Sep 23 - Sep 24
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A spacious living room with large windows, a sofa, a chair, and a small table.

16. 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, (12 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 ￥10,354
￥43,434 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! MCM-Style Home in Brunswick
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

17. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
9.8 out of 10, Exceptional, (10 reviews)
The price is ￥63,028
￥146,847 total
includes taxes & fees
Sep 28 - Sep 29
Three bedroom in United States of America, Freeport
A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

18. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is ￥53,653
￥95,589 total
includes taxes & fees
Oct 5 - Oct 6
Lush Coastal Downtown Home - Beaches & Shopping
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

19. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is ￥23,061
￥77,120 total
includes taxes & fees
Sep 23 - Sep 24
Fully Updated Airy Historic Home in South Freeport
A lush garden with a hammock, a variety of flowers, and a lake in the background.

20. 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 ￥72,949
￥286,252 total
includes taxes & fees
Oct 12 - Oct 13
Classic New England Waterfront House Big Lawn Beautiful Sunrise
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"This hotel was right in the middle of Old Port and in such close proximity to all of the amazing restaurants and stores. The staff was incredibly attentive and so friendly. We never had to wait more than a couple minutes for anything. Even the restaurant and bar in the hotel was great and the food was delicious"
Brianne Renee 3-night trip
Posted 3 hours ago
Portland Regency Hotel & Spa

Find out more about Great Diamond Island

Great Diamond Island Vacation Homes information

Number of reviews
Accommodation
589 Vacation Homes
Lowest Price
￥429,142
Highest Price
￥429,142

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