Photo by Robbie Martin

Holiday Homes in Great Diamond Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Featured Holiday Homes in Great Diamond Island and around

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 €245
includes taxes & fees
1 Oct - 2 Oct
Camp Forever cottage

Escape to Positive Outlook

Escape to Positive Outlook

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is €220
includes taxes & fees
8 Sept - 9 Sept
Willard Beach–Private Apt Near Portland & Parks

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."
The price is €217
includes taxes & fees
2 Sept - 3 Sept
Mid Coast Getaway w/ water views

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

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is €156
includes taxes & fees
2 Sept - 3 Sept
Private Entrance Residential Portland

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (4)
"GoodLocation, very clean. Would stay again "
Luxury on Back Cove - Three Gables

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
Sauna & fire table near Portland's Back Cove

Full sized home

9.8 out of 10, Exceptional, (37)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is €317
includes taxes & fees
2 Sept - 3 Sept
Full sized home

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."
Orchid Harbor, Bailey Island 3BR

Bright 3 bedroom located in the heart of OOB

9.0 out of 10, Wonderful, (4)
"Perfect for our needs. Pictures don't do it justice, it is roomier than it looks. Would definitely book it again. "
The price is €602
includes taxes & fees
1 Oct - 2 Oct
Bright 3 bedroom located in the heart of OOB

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 €201
includes taxes & fees
3 Sept - 4 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland

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

10.0 out of 10, Exceptional, (4)
"Very clean "
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

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 €386
includes taxes & fees
12 Sept - 13 Sept
Fantastic Waterfront Views

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

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

10.0 out of 10, Exceptional, (2)
"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

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (1)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
The price is €456
includes taxes & fees
2 Sept - 3 Sept
Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is €406
includes taxes & fees
2 Sept - 3 Sept
Entire Modern Chic Home in Windham

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

9.4 out of 10, Exceptional, (3)
"This space was fresh and clean, and close to everything.Check in and out was easy. We enjoyed our stay."
The price is €319
includes taxes & fees
29 Sept - 30 Sept
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

9.4 out of 10, Exceptional, (3)
"Really nice place. Beds are comfortable. Had nice hot tub with propane fire. Lovely back patio. "
The price is €588
includes taxes & fees
7 Sept - 8 Sept
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Great Diamond Island Hotel Reviews

Find out more about Great Diamond Island

Find out more about Great Diamond Island

Great Diamond Island Holiday Homes information

Number of reviews
Accommodation
599 Holiday Homes
Lowest Price
€241
Highest Price
€779