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Holiday Homes in Great Diamond Island

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Featured Holiday Homes in Great Diamond Island and around

Luxury King Room with Parlor and Balcony

The price is €616
includes taxes & fees
7 Sept - 8 Sept
Luxury King Room with Parlor and Balcony

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is €239
includes taxes & fees
15 Sept - 16 Sept
Willard Beach–Private Apt Near Portland & Parks

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is €262
includes taxes & fees
17 Sept - 18 Sept
Camp Forever cottage

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
30 Acres with Woodland Trails and Playground

Two-story dog-friendly house with enclosed yard, grill, patio, W/D

2.0 star property
9.4 out of 10, Exceptional, (11)
"Nice place. Recommended. "
Two-story dog-friendly house with enclosed yard, grill, patio, W/D

Mid Coast Getaway w/ water views

9.0 out of 10, Wonderful, (2)
"You couldn’t ask for a better view, it was everything we had hoped and more."
Mid Coast Getaway w/ water views

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is €328
includes taxes & fees
21 Aug - 22 Aug
Sauna & fire table near Portland's Back Cove

Serenity between the lakes and seashore

9.8 out of 10, Exceptional, (21)
"Good location near lots of hiking and not far from Portland "
Serenity between the lakes and seashore

Full sized home

9.8 out of 10, Exceptional, (33)
"Very clean and comfortable. Great care has gone into making it feel like a home well loved."
Full sized home

Escape to Positive Outlook

Escape to Positive Outlook

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (2)
"This apartment is great- the furnishings are cute and the bed is comfy. It has a kitchen with all of the cookware I needed, and off-street parking is awesome. I liked that it was really convenient to downtown, but outside of the busy, touristy parts of town. The owners were communicative, but not intrusive. It was overall a great experience. I would definitely stay here again."
The price is €156
includes taxes & fees
19 Aug - 20 Aug
Private Entrance Residential Portland

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is €203
includes taxes & fees
14 Sept - 15 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is €410
includes taxes & fees
21 Aug - 22 Aug
Entire Modern Chic Home in Windham

Bright 3 bedroom located in the heart of OOB

9.0 out of 10, Wonderful, (2)
"We had a good time. Plenty of parking for our 3 vehicles. Bedrooms small and 1 that is only large enough for the bed and connected to a very small toilet and sink. Downstairs lovely space and a short ealk to the beach. Overall very good "
The price is €356
includes taxes & fees
18 Sept - 19 Sept
Bright 3 bedroom located in the heart of OOB

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

10.0 out of 10, Exceptional, (1)
"We had a fantastic stay at this peaceful oceanside property in Harpswell, Maine. The setup—with a main house, attached apartment, and a charming bunkhouse—was perfect for our two families and adult children. There was plenty of space for everyone to relax and unwind.The backyard is absolutely stunning, filled with beautiful flowers and lush grass, and it opens up to a tranquil ocean inlet. We especially loved the hammock spot, perfect for a good book or an afternoon nap, and the back porch...
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is €507
includes taxes & fees
19 Aug - 20 Aug
Luxury on Back Cove - Three Gables

Fantastic Waterfront Views

9.8 out of 10, Exceptional, (7)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
The price is €439
includes taxes & fees
20 Aug - 21 Aug
Fantastic Waterfront Views

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

10.0 out of 10, Exceptional, (4)
"Very clean "
The price is €411
includes taxes & fees
11 Sept - 12 Sept
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (3)
"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."
The price is €437
includes taxes & fees
16 Sept - 17 Sept
Orchid Harbor, Bailey Island 3BR

Oceanside escape 🌊 perfect family getaway!

9.8 out of 10, Exceptional, (18)
"Great location for proximity to Portland. Very clean and spacious."
Oceanside escape 🌊 perfect family getaway!
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