Great Diamond Island Vacation Rentals

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Our top choices for Great Diamond Island vacation rentals

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.4 out of 10, Exceptional, (22 reviews)
"The room was spotless. The hotel was very clean and the staff was very friendly and helpful."
United States
Monique
The price is CA $157
CA $172 total
includes taxes & fees
Apr 21 - Apr 22
HomeAwhile

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
The price is CA $370
CA $609 total
includes taxes & fees
May 3 - May 4
Evalina Hotel

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.
The price is CA $276
CA $629 total
includes taxes & fees
Apr 27 - Apr 28
Mere Point Sunrise Views at Eastern Shore!

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is CA $259
CA $466 total
includes taxes & fees
Apr 20 - Apr 21
Camp Forever cottage

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.
The price is CA $290
CA $483 total
includes taxes & fees
Apr 20 - Apr 21
Modern, Luxurious Cabin in the Woods - 03

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
The price is CA $404
CA $654 total
includes taxes & fees
Apr 20 - Apr 21
Centerview cottage

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.
The price is CA $160
CA $333 total
includes taxes & fees
Apr 20 - Apr 21
Pine Point Beach private, quaint, charming studio.

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.
The price is CA $144
CA $295 total
includes taxes & fees
Apr 20 - Apr 21
2 bedroom w/ expansive water views

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.
The price is CA $173
CA $356 total
includes taxes & fees
Apr 20 - Apr 21
Fantastic Waterfront Views

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.
The price is CA $342
CA $588 total
includes taxes & fees
May 14 - May 15
Full sized home

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.
The price is CA $333
CA $551 total
includes taxes & fees
Apr 26 - Apr 27
Large, luxurious geodesic dome - 04

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.
The price is CA $1,042
CA $1,554 total
includes taxes & fees
Apr 20 - Apr 21
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

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.
The price is CA $144
CA $294 total
includes taxes & fees
Apr 27 - Apr 28
Mid Coast Getaway w/ water views

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.
The price is CA $685
CA $1,467 total
includes taxes & fees
May 5 - May 6
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

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.
The price is CA $404
CA $776 total
includes taxes & fees
Apr 22 - Apr 23
The Globe House on Munjoy Hill - Walk to Breweries

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (173 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is CA $242
CA $439 total
includes taxes & fees
Apr 23 - Apr 24
Glorious getaway on Portland's Eastern Promenade.

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.
The price is CA $229
CA $474 total
includes taxes & fees
Apr 20 - Apr 21
Modern & Sunny House Steps from the Promenade. Private Parking!

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (99 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
The price is CA $287
CA $416 total
includes taxes & fees
May 11 - May 12
The Weldon Hotel

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is CA $154
CA $295 total
includes taxes & fees
Apr 20 - Apr 21
Charming Studio apartment with WiFi, AC in welcoming Portland

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"What a wonderful weekend in Portland Maine. The property was exceptional and in a great area. We felt comfortable and safe for our stay. We had a great time!"
United States
Kristyn E.
The price is CA $404
CA $725 total
includes taxes & fees
Apr 20 - Apr 21
Harborview - Curated East End Escape w/ Parking
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

Find out more about Great Diamond Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Great Diamond Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.