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

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Great Diamond Island

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (48)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (51)
"We loved our stay in Munjoy Hill at Mark's VRBO property! It was super clean and modern and in a fantastic location. We were able to walk all over the city from here! Close to so many great restaurants. It was also super private--loved the little deck off the back and the changing leaves. Would definitely stay here again!"
Sunny Modern Oasis in Portland’s Trendy East End

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (27)
"The home was in a great neighborhood and the place was very clean. My family and I enjoyed staying here."
Convenient Portland home 3 miles from Downtown

Beachfront, Just steps and you're on the beach!

10.0 out of 10, Exceptional, (1)
"We loved our stay at the cottage. It was exceptionally clean and quiet. "
Beachfront, Just steps and you're on the beach!

NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

10.0 out of 10, Exceptional, (2)
"We could not have been more pleased with our experience. Not only is the home beautiful and cozy, but the attention to detail is beyond any expectations. The entire process was smooth as could be and the property was an excellent base for our visit to the area. Everything was considered - more amenities than you would imagine and also completely top notch. Excellent views, comfortable beds, luxurious towels, fully appointed kitchen, etc. We felt so lucky to be there."
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.4 out of 10, Very good, (53)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Quaint Cottage Vacation

9.0 out of 10, Wonderful, (26)
"Had a great time!!"
Quaint Cottage Vacation

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (127)
"John was great and the view was a amazing"
Charming 110-year former Inn 10' from the Ocean!

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (11)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

8.6 out of 10, Excellent, (39)
"Super clean and excellent location with a view."
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

Spacious 5BR Family Dream with Private Beach Access

10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
Spacious 5BR Family Dream with Private Beach Access

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

9.6 out of 10, Exceptional, (64)
"We thoroughly enjoyed our stay at the Portland Cottage! It was a wonderful location, extremely clean, and incredible cozy. Paul is a delightful host!"
New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Beautiful Oceanfront House- Stunning Water Views

9.8 out of 10, Exceptional, (7)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views

Enchanting 3BR Farmhouse Retreat Nature Getaway

10.0 out of 10, Exceptional, (3)
"We really enjoyed this property. It was very clean, and very comfortable. We will visit again. "
Enchanting 3BR Farmhouse Retreat Nature Getaway

The Lori House in Westbrook

10.0 out of 10, Exceptional, (1)
The Lori House in Westbrook

ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!

10.0 out of 10, Exceptional, (43)
"Cleanest and updated house we have stayed in, I highly recommend. "
ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
8.8 out of 10, Excellent, (6)
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Water-view retreat with beach access, deck, grill, EV charger & lawn games

9.8 out of 10, Exceptional, (18)
"The house was fantastic. Serene, clean and beautiful setting. Would stay here again and again."
Water-view retreat with beach access, deck, grill, EV charger & lawn games
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