Photo by Robbie Martin

Holiday Homes in Great Diamond Island

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Featured Holiday Homes in Great Diamond Island

TV
Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!

Brunswick
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is NZ$667
includes taxes & fees
16 Nov - 17 Nov
Mere Point Sunrise Views at Eastern Shore!
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
The price is NZ$290
includes taxes & fees
16 Nov - 17 Nov
The Outlet Studio, Rustic Comfort w Fireplace
Property grounds
Centerview cottage

Centerview cottage

Harpswell
9.6 out of 10, Exceptional, (59)
"We loved the view! The hosts were very quick to respond to any questions. This is a lovely spot to relax and watch the sea."
United States
Anonymous traveller
The price is NZ$664
includes taxes & fees
1 Dec - 2 Dec
Centerview cottage
Outdoor dining
Camp Forever cottage

Camp Forever cottage

Harpswell
9.6 out of 10, Exceptional, (57)
"Nice, quiet location. Bed is super comfortable, and everything is neat and clean inside. We were a little confused which kayaks we could use and how to get them down to the water, and we were encouraged to use life vests, but there were none available (and we did not bring any with us). Otherwise, hosts were very responsive and we had a nice time."
United States
Lisa K.
The price is NZ$683
includes taxes & fees
30 Nov - 1 Dec
Camp Forever cottage
3 bedrooms, desk, iron/ironing board, travel cot
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

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

Old Orchard Beach
10.0 out of 10, Exceptional, (5)
"I loved that the hosts live nearby and responded quickly when we needed anything. Having a washer and dryer onsite is great for longer stays. Beds were comfortable and plenty of blankets and pillows. Highly recommend this property."
United States
Terry
The price is NZ$625
includes taxes & fees
16 Nov - 17 Nov
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (13)
"The place is amazing with lots of room for a family, and great views of the water from almost everywhere. The neighborhood is quiet and the people were very friendly. "
United States
Joseph V.
The price is NZ$476
includes taxes & fees
30 Nov - 1 Dec
Fantastic Waterfront Views
Interior
Serenity between the lakes and seashore

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (24)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
The price is NZ$549
includes taxes & fees
29 Nov - 30 Nov
Serenity between the lakes and seashore
Beach nearby, sun-loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay the weekend after Christmas. The home had absolutely everything we needed and was both comfortable and beautiful! Everything was clearly labeled and so easy settle in. Very close to the beach which was awesome to visit even in the winter!"
United States
Elizabeth M.
The price is NZ$852
includes taxes & fees
15 Nov - 16 Nov
Beach House ∆ Prime Location ∆ Steps to the Ocean
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick
8.8 out of 10, Excellent, (23)
"Great location for baileys island and popham"
United States
Anonymous traveller
The price is NZ$707
includes taxes & fees
16 Nov - 17 Nov
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
TV
Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views

West Point
9.2 out of 10, Wonderful, (5)
"You couldn’t ask for a better view, it was everything we had hoped and more."
United States
Andrew S.
The price is NZ$357
includes taxes & fees
18 Nov - 19 Nov
Mid Coast Getaway w/ water views
Fridge, microwave, oven, stovetop
Beautiful 3BR Home with Office in Town of Brunswick with King beds

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

Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is NZ$620
includes taxes & fees
17 Nov - 18 Nov
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Beach
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Harpswell
9.8 out of 10, Exceptional, (7)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
United States
Jason M.
The price is NZ$734
includes taxes & fees
24 Nov - 25 Nov
Orchid Harbor, Bailey Island 3BR
Terrace/patio
Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!

Munjoy Hill
10.0 out of 10, Exceptional, (35)
"Adorable and pristine place, with many thoughtful amenities. Great location. Incredible host. Loved our stay."
United States
Brant H.
The price is NZ$646
includes taxes & fees
16 Nov - 17 Nov
Modern & Sunny House Steps from the Promenade. Private Parking!
1 bedroom, Internet, bed sheets
Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood

Back Cove
The price is NZ$412
includes taxes & fees
20 Nov - 21 Nov
Charming 1-bedroom ADU in wonderful Portland neighborhood
Beach
Upscale Spacious OOB Beach House - Seasonal Heated Pool

Upscale Spacious OOB Beach House - Seasonal Heated Pool

Old Orchard Beach
10.0 out of 10, Exceptional, (11)
"clean and comfortable. close to everything and had all we needed."
United States
mark g.
The price is NZ$842
includes taxes & fees
17 Nov - 18 Nov
Upscale Spacious OOB Beach House - Seasonal Heated Pool
Private kitchen
Classic New England Waterfront

Classic New England Waterfront

Harpswell
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay! "
United States
Ashma B.
The price is NZ$1,256
includes taxes & fees
1 Dec - 2 Dec
Classic New England Waterfront
Private kitchen
Spacious 5BR Family Dream with Private Beach Access

Spacious 5BR Family Dream with Private Beach Access

Old Orchard Beach
10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
United States
rebecca c.
The price is NZ$917
includes taxes & fees
19 Nov - 20 Nov
Spacious 5BR Family Dream with Private Beach Access
Fridge, microwave, oven, stovetop
Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach

Saco
8.0 out of 10, Very good, (1)
"The only big issue was that the VRBO listing gave us the wrong address. It sent us to Scarborough instead of Saco. Luckily we were familiar with the area and I knew that Saco was close to Old Orchard Beach, which was mentioned in the listing, so I did a google map search of the same address in Saco and it looked like the pictures. My elderly parents were relieved that we didn’t get scammed. Lol. The place was clean and large and easy to get on the highway. It’s 2 and a half baths, not 3 full...
United States
Stacy H.
The price is NZ$970
includes taxes & fees
17 Nov - 18 Nov
Huge New Townhome 10mins from the Beach
Living area
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach
9.4 out of 10, Exceptional, (14)
"The property was in a good location from everything available in the beach area and the house had enough space to accommodate all 12 of us."
United States
Wayne R.
The price is NZ$836
includes taxes & fees
16 Nov - 17 Nov
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Fridge, microwave, oven, stovetop
Modern Getaway by the Sea

Modern Getaway by the Sea

Cash Corner
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is NZ$739
includes taxes & fees
28 Nov - 29 Nov
Modern Getaway by the Sea
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Diamond Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Fantastic service and comfortable rooms."
Matthew 4-night trip
Posted 2 days ago
Portland Harbor Hotel

Find out more about Great Diamond Island

Great Diamond Island Holiday Homes information

Number of reviews
Accommodation
 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia