Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Great Diamond Island vacation rentals

House (2 Bedrooms) | Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
$247 nightly
The price is $270
Jun 2 - Jun 3
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
$304 nightly
The price is $332
May 31 - Jun 1
Total with taxes and fees
Modern, Luxurious Cabin in the Woods - 03
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
$348 nightly
The price is $379
May 31 - Jun 1
Total with taxes and fees
Large, luxurious geodesic dome - 04
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
$256 nightly
The price is $273
Jun 2 - Jun 3
Total with taxes and fees
2 bedroom w/ expansive water views
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$337 nightly
The price is $367
May 29 - May 30
Total with taxes and fees
Camp Forever cottage
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
$411 nightly
The price is $449
Jun 4 - Jun 5
Total with taxes and fees
Fortland Island Campground
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
$227 nightly
The price is $241
May 31 - Jun 1
Total with taxes and fees
Mid Coast Getaway w/ water views
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
$276 nightly
The price is $301
Jun 8 - Jun 9
Total with taxes and fees
Sunny Spot with Private Parking.
3 bedrooms, WiFi, bed sheets

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$311 nightly
The price is $313
Jun 1 - Jun 2
Total with taxes and fees
Fantastic Waterfront Views
Beach nearby, sun loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (39 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
$319 nightly
The price is $348
May 31 - Jun 1
Total with taxes and fees
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Interior

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

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (69 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
$250 nightly
The price is $273
May 31 - Jun 1
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Interior

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Saco
9.2 out of 10, Wonderful, (15 reviews)
"Had a great stay, very private property. House was very clean and user friendly. Would definitely stay again, thanks"
United States
Doug C.
$309 nightly
The price is $337
Jun 2 - Jun 3
Total with taxes and fees
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
$434 nightly
The price is $473
May 29 - May 30
Total with taxes and fees
Centerview cottage
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful stay!"
United States
Erika T.
$338 nightly
The price is $368
Jun 3 - Jun 4
Total with taxes and fees
Full sized home
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
$275 nightly
The price is $300
Jun 28 - Jun 29
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
$305 nightly
The price is $332
Jun 7 - Jun 8
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Children's area

Clean cozy cottage 1 mile from beach.

Clean cozy cottage 1 mile from beach.
Old Orchard Beach
8.0 out of 10, Very Good, (11 reviews)
"This house met all of our needs. It was updated and clean and has a nice little quiet enclosed back yard with a fire pit, grill and dining area. "
United States
Alyssa F.
$464 nightly
The price is $506
May 31 - Jun 1
Total with taxes and fees
Clean cozy cottage 1 mile from beach.
1 bedroom, internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
$254 nightly
The price is $277
May 31 - Jun 1
Total with taxes and fees
Charming 1-bedroom ADU in wonderful Portland neighborhood
Property grounds

City Oasis and Spa/Close to Beaches

City Oasis and Spa/Close to Beaches
Downtown Saco
$325 nightly
The price is $354
May 30 - May 31
Total with taxes and fees
City Oasis and Spa/Close to Beaches
Beach

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
$312 nightly
The price is $340
Jun 1 - Jun 2
Total with taxes and fees
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Our room was wonderful! Very spacious and comfortable. The staff were very attentive and helpful. Valet parking went very smoothly; it ran efficiently and the attendants were very thoughtful and helpful. Our only minor disappointments were that the breakfast was not as good as we had expected and some issues with Wi-Fi but a staff member was able to assist us. The location of the Regency was perfect; we were able to walk very easily to Merrill Auditorium and back from our dinner after the concert we attended."
Ina 2-night trip
Posted 2 hours ago
Portland Regency Hotel & Spa

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Diamond Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Diamond Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Great Diamond Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $166 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Great Diamond Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Diamond Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Diamond Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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