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Our top choices for Great Diamond Island vacation homes

1. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"This cute house is perfect located next to Scratch bakery and Scoops ice cream and just steps from Willard Beach ! If you are looking for an idyllic New England vacation, you found it !Looking forward to next summer !!"
United States
Richard D.
The price is AED 1,315
AED 2,248 total
includes taxes & fees
16 Nov - 17 Nov
Willard Square Family Home

2. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is AED 2,562
AED 3,701 total
includes taxes & fees
16 Nov - 17 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

3. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.4 out of 10, Very good, (65 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

4. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,146
AED 1,857 total
includes taxes & fees
16 Nov - 17 Nov
Modern & Sunny East End House.

5. 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, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is AED 1,855
AED 3,027 total
includes taxes & fees
16 Nov - 17 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.

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, (17 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 AED 1,521
AED 2,806 total
includes taxes & fees
22 Nov - 23 Nov
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

7. Charming West End Victorian

Charming West End Victorian
Parkside
The price is AED 781
AED 2,556 total
includes taxes & fees
2 Dec - 3 Dec
Charming West End Victorian

8. 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 AED 606
AED 2,138 total
includes taxes & fees
16 Nov - 17 Nov
Spacious Portland Home + Parking

9. The 87th Townhome by Everrow

The 87th Townhome by Everrow
West End
9.6 out of 10, Exceptional, (11 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 AED 617
AED 1,733 total
includes taxes & fees
16 Nov - 17 Nov
The 87th Townhome by Everrow

10. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space
Downtown Portland
The price is AED 2,468
AED 4,548 total
includes taxes & fees
16 Nov - 17 Nov
Steps to Old Port, balcony, private outdoor space

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 AED 6,913
AED 9,877 total
includes taxes & fees
16 Nov - 17 Nov
Charming Historic Estate | In-town location

12. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AED 396
AED 1,259 total
includes taxes & fees
16 Nov - 17 Nov
Quiet Spot in lovely Freeport neighborhood

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 AED 525
AED 1,694 total
includes taxes & fees
16 Nov - 17 Nov
Fully Updated Airy Historic Home in South Freeport

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 AED 602
AED 1,448 total
includes taxes & fees
13 Dec - 14 Dec
Orchid Harbor, Bailey Island 3BR

15. 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 AED 386
AED 736 total
includes taxes & fees
16 Nov - 17 Nov
Mid Coast Getaway w/ water views

16. 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 AED 1,286
AED 5,597 total
includes taxes & fees
30 Nov - 1 Dec
Classic New England Waterfront House Big Lawn Beautiful Sunrise

17. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"This little spot was an ideal getaway for our family’s summer trip to Maine. We very much enjoyed the porch with a view of the water and felt right at home here."
United States
James C.
The price is AED 443
AED 1,278 total
includes taxes & fees
17 Nov - 18 Nov
Mere Point Sunrise Views at Eastern Shore!

18. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
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 AED 1,664
AED 3,331 total
includes taxes & fees
16 Nov - 17 Nov
Heated Game Room, Coastal Maine Cape Sleeps 10

19. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Great house! Enjoyed our stay very much. Comfortable, clean, and many nice extra touches i.e. games, books."
United States
Jill J.
The price is AED 735
AED 1,277 total
includes taxes & fees
1 Dec - 2 Dec
Full sized home

20. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is AED 765
AED 2,427 total
includes taxes & fees
22 Nov - 23 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
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.

Learn more about Great Diamond Island

Check out Sand Beach and East End Beach—just a couple of the sights around Great Diamond Island.

A calm sea with a sailboat and rocky coastline.

Top reviews in Great Diamond Island

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