Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Great Diamond Island vacation rentals

Living area

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
$408 nightly
The price is $445
May 3 - May 4
Total with taxes and fees
Evalina Hotel
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"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.
$394 nightly
The price is $398
Apr 16 - Apr 17
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
Fitness facility

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.4 out of 10, Exceptional, (21 reviews)
"The room was spotless. The hotel was very clean and the staff was very friendly and helpful."
United States
Monique
$104 nightly
The price is $113
Apr 26 - Apr 27
Total with taxes and fees
HomeAwhile
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.
$309 nightly
The price is $337
Apr 12 - Apr 13
Total with taxes and fees
Camp Forever cottage
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (6 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.
$273 nightly
The price is $297
Apr 12 - Apr 13
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, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
$310 nightly
The price is $338
Apr 12 - Apr 13
Total with taxes and fees
Large, luxurious geodesic dome - 04
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
Apr 12 - Apr 13
Total with taxes and fees
Centerview cottage
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (28 reviews)
"The place was extremely clean."
United States
Matthew D.
$225 nightly
The price is $245
Apr 12 - Apr 13
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Deluxe Suite, 1 King Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (98 reviews)
"The hotel is in an ideal location in downtown Portland. The staff is so kind and very accommodating! The stay was beyond comfortable and is the place we will stay every time we return to Portland!"
United States
Lauren
$244 nightly
The price is $259
Apr 19 - Apr 20
Total with taxes and fees
The Weldon Hotel
3 bedrooms, WiFi

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.
$246 nightly
The price is $248
Apr 13 - Apr 14
Total with taxes and fees
Fantastic Waterfront Views
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
$335 nightly
The price is $365
Apr 13 - Apr 14
Total with taxes and fees
Full sized home
Exterior

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Portland
9.8 out of 10, Exceptional, (35 reviews)
"Fabulous place. Peaks Island. "
United States
Christopher W.
$1,052 nightly
The price is $1,147
May 5 - May 6
Total with taxes and fees
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
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.
$205 nightly
The price is $217
Apr 12 - Apr 13
Total with taxes and fees
2 bedroom w/ expansive water views
Exterior

A historic treasure in Southern Maine, very unique and spacious

A historic treasure in Southern Maine, very unique and spacious
Biddeford
10.0 out of 10, Exceptional, (44 reviews)
"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "
United States
Jeanne C.
$925 nightly
The price is $1,008
Apr 12 - Apr 13
Total with taxes and fees
A historic treasure in Southern Maine, very unique and spacious
Outdoor dining

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
$520 nightly
The price is $567
Apr 22 - Apr 23
Total with taxes and fees
The Globe House on Munjoy Hill - Walk to Breweries
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (71 reviews)
"Had a really nice stay. "
United States
John F.
$1,097 nightly
The price is $1,196
Apr 13 - Apr 14
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
3 bedrooms, desk, iron/ironing board, travel crib

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, (7 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
$388 nightly
The price is $391
Apr 12 - Apr 13
Total with taxes and fees
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Microwave, oven, stovetop, dishwasher

Toast to 2026! Free Champagne for all Jan / Feb Bookings

Toast to 2026! Free Champagne for all Jan / Feb Bookings
South Portland
10.0 out of 10, Exceptional, (5 reviews)
"The house was very nice and had great accommodations for our group. The kitchen and living room was very accommodating for meals and hangouts and we were close to all of the activities we were looking to do"
United States
Justin R.
Toast to 2026! Free Champagne for all Jan / Feb Bookings
Outdoor dining

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, (39 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
$309 nightly
The price is $337
Apr 12 - Apr 13
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!
On the beach, sun loungers, beach towels

Willard by the Sea # 4, Elevated Coastal Living + Walkable Charm Near Portland

Willard by the Sea # 4, Elevated Coastal Living + Walkable Charm Near Portland
Willard
10.0 out of 10, Exceptional, (13 reviews)
"The apartment was very clean and well appointed with everything you might need. The host was very friendly and attentive and check in and check out were very simple. Any questions I had were answered promptly. I would definitely stay here again!"
United States
Diana T.
$473 nightly
The price is $516
Apr 12 - Apr 13
Total with taxes and fees
Willard by the Sea # 4, Elevated Coastal Living + Walkable Charm Near Portland
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Our family of 4 stayed over the Easter holiday and had a big corner room with beautiful views. Beds were comfortable but pillows were flat, even though there were three per person. The room was very clean. Breakfast was not the best as items were out of stock and we were told at 8:45 that they just didn’t have refills, such as milk and cut fruit. "
Michele 4-night trip
Posted 1 hour ago
Hampton Inn Portland Downtown - Waterfront

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 $113 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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