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Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Great Diamond Island Vacation Homes

Luxury King Room with Parlor and Balcony
Property grounds

Luxury King Room with Parlor and Balcony

The price is CA $441
CA $972 total
includes taxes & fees
Sep 7 - Sep 8
Luxury King Room with Parlor and Balcony
30 Acres with Woodland Trails and Playground
Fridge, microwave, oven, stovetop

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. "
The price is CA $138
CA $640 total
includes taxes & fees
Aug 26 - Aug 27
30 Acres with Woodland Trails and Playground
Camp Forever cottage
Outdoor dining

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 CA $206
CA $395 total
includes taxes & fees
Sep 16 - Sep 17
Camp Forever cottage
Willard Beach–Private Apt Near Portland & Parks
Interior

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is CA $166
CA $371 total
includes taxes & fees
Sep 15 - Sep 16
Willard Beach–Private Apt Near Portland & Parks
Mid Coast Getaway w/ water views
TV

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 CA $290
CA $474 total
includes taxes & fees
Aug 24 - Aug 25
Mid Coast Getaway w/ water views
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (34)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is CA $282
CA $504 total
includes taxes & fees
Aug 25 - Aug 26
Full sized home
Two-story dog-friendly house with enclosed yard, grill, patio, W/D
Fridge, microwave, oven, stovetop

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

2.0 star property
9.4 out of 10, Exceptional, (11)
"A clean, beautiful home. It had lots of amenities and space. We had every thing we needed. It felt like home. We will definitely stay there again. "
The price is CA $234
CA $713 total
includes taxes & fees
Sep 12 - Sep 13
Two-story dog-friendly house with enclosed yard, grill, patio, W/D
Escape to Positive Outlook
Dining

Escape to Positive Outlook

The price is CA $248
CA $428 total
includes taxes & fees
Aug 26 - Aug 27
Escape to Positive Outlook
Sauna & fire table near Portland's Back Cove
Terrace/patio

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is CA $242
CA $514 total
includes taxes & fees
Sep 7 - Sep 8
Sauna & fire table near Portland's Back Cove
Entire Modern Chic Home in Windham
Fridge, microwave, oven, stovetop

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is CA $311
CA $647 total
includes taxes & fees
Aug 29 - Aug 30
Entire Modern Chic Home in Windham
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Fridge, microwave, oven, stovetop

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 price is CA $899
CA $2,066 total
includes taxes & fees
Sep 23 - Sep 24
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

8.8 out of 10, Excellent, (3)
"Check in was simple. Quaint place. "
The price is CA $145
CA $246 total
includes taxes & fees
Aug 25 - Aug 26
Private Entrance Residential Portland
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

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 CA $173
CA $316 total
includes taxes & fees
Sep 3 - Sep 4
Charming Studio apartment with WiFi, AC in welcoming Portland
Orchid Harbor, Bailey Island 3BR
Interior

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 CA $302
CA $657 total
includes taxes & fees
Sep 21 - Sep 22
Orchid Harbor, Bailey Island 3BR
Luxury on Back Cove - Three Gables
Fridge, microwave, oven, stovetop

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (3)
"GoodLocation, very clean. Would stay again "
The price is CA $345
CA $732 total
includes taxes & fees
Sep 16 - Sep 17
Luxury on Back Cove - Three Gables
Fantastic Waterfront Views
3 bedrooms, WiFi

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 CA $436
CA $699 total
includes taxes & fees
Sep 5 - Sep 6
Fantastic Waterfront Views
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Fridge, microwave, oven, stovetop

Beautiful 3BR Home with Office in Town of Brunswick with King beds

9.2 out of 10, Wonderful, (5)
"Had a great stay here, the property was clean and came as advertised"
The price is CA $415
CA $770 total
includes taxes & fees
Aug 27 - Aug 28
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

8.0 out of 10, Very good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is CA $153
CA $256 total
includes taxes & fees
Aug 24 - Aug 25
Studio Unit Walkable Everywhere
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
3 bedrooms, desk, iron/ironing board, travel crib

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

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 CA $207
CA $508 total
includes taxes & fees
Sep 4 - Sep 5
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco
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

Germaine Inn South Portland

Germaine Inn South Portland

10/10 Excellent
"Staff was great rooms were clean and overall hotel was a good stay for the rooms being for pet owners. It far exceeded what my family needed. I was pleasantly surprised. Gas station nearby for convenience and plenty of food places within 5 mile radius "
Brandy 3-night trip
Posted 16 hours ago
Germaine Inn South Portland