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
  • 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

Our top choices for Great Diamond Island holiday homes

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is €166
includes taxes & fees
4 Jan - 5 Jan
Escape to Positive Outlook

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is €234
includes taxes & fees
5 Jan - 6 Jan
Fantastic Waterfront Views

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, (6)
"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
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50)
"It was a very nice house to stay at. "
United States
Anonymous traveller
The price is €316
includes taxes & fees
26 Jan - 27 Jan
Full sized home

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
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is €350
includes taxes & fees
4 Jan - 5 Jan
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (9)
"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."
United States
Karen T.
Orchid Harbor, Bailey Island 3BR

Maine Luxury Home On the Sea

Maine Luxury Home On the Sea
Brunswick
The price is €543
includes taxes & fees
5 Jan - 6 Jan
Maine Luxury Home On the Sea

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)
"Excellent location for an after Labor Day vacation. Easy access to the beach. Quiet street. Very nice accommodations with plenty of room. "
United States
Charles C.
The price is €412
includes taxes & fees
6 Jan - 7 Jan
Beach House ∆ Prime Location ∆ Steps to the Ocean

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, (38)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is €288
includes taxes & fees
4 Jan - 5 Jan
Modern & Sunny House Steps from the Promenade. Private Parking!

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is €464
includes taxes & fees
4 Jan - 5 Jan
Modern Getaway by the Sea

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (7)
"We had a fantastic stay. Alexa was a wonderful host!"
United States
Desmond L.
The price is €513
includes taxes & fees
6 Jan - 7 Jan
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

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 €433
includes taxes & fees
4 Jan - 5 Jan
Huge New Townhome 10mins from the Beach

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)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is €422
includes taxes & fees
4 Jan - 5 Jan
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (58)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is €263
includes taxes & fees
2 Feb - 3 Feb
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
2.0 star property
Windham
Modern Lakeview Escape | 3BR/2BA

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
Charming 1-bedroom ADU in wonderful Portland neighborhood

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 €425
includes taxes & fees
4 Jan - 5 Jan
Spacious 5BR Family Dream with Private Beach Access

Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
2.0 star property
Munjoy Hill
10.0 out of 10, Exceptional, (2)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
The price is €349
includes taxes & fees
18 Jan - 19 Jan
Chic 3-bedroom house in Munjoy Hill with off-street parking.

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

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is €993
includes taxes & fees
6 Jan - 7 Jan
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
Modern Cottage with Peeks of Ocean Views
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

Great Diamond Island Holiday Homes information

Number of reviews
279
Accommodation
559 Holiday Homes
Lowest Price
€234
Highest Price
€993

Explore a world of travel with Expedia