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Search Cottages in Great Diamond Island

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Compare 133 Cottages in Great Diamond Island with updated reviews, rates, and availability.

Little Miss Cottages
2.5 star property
8.4 out of 10, Very Good, (81)
"Great location and cute cabins. We have been coming to OOB for years and this is the best pet friendly rental!"
Little Miss Cottages
Clean cozy cottage 1 mile from beach.
7.6 out of 10, Good, (7)
"We had a great time in OOB. The house is just awesome and very confortable for all six of us. Looks recently renovated and well maintained. Great and quiet location, not far from the beautiful beaches, and far enough from the city center and its crowd. Great communications with Pete the owner. No concerns and I highly recommend!"
The price is AED 511
AED 1,437 total
includes taxes & fees
29 Sep - 30 Sep
Clean cozy cottage 1 mile from beach.
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.6 out of 10, Exceptional, (34)
"Perfect rental for me and my dog. Lots of windows and light, with gorgeous views right on the water. The deck is fantastic. Great location - very quiet (except the gulls and an occasional owl), but also convenient to restaurants and such. Kitchen had everything I needed and furniture was all lovely and comfy. "
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Highland Lakefront Cabin
9.0 out of 10, Wonderful, (74)
"Beautiful setting and comfortable cottage. We were there during hot spell and air conditioner did not keep up. That said, the beds were comfortable and the place was clean. There was a bit of an ant issue- hard to control that during that time of year. Would definitely go again- had a great time "
Highland Lakefront Cabin
Classic Maine Beach Cottage **** Fabulous location!
9.4 out of 10, Exceptional, (23)
"The property was great for our family of 4. We enjoyed cooking at the property each night and playing board games or TV in the evening. The location is great for walking on the shore, and for many nearby parks that we took full advantage of with our bikes that we brought. We especially liked biking to Macworth Island State Park, and taking our bikes on the Ferry to Chebeague Island. Also, the local market had great informal lunch after one of our bikerides, and lovely ice-cream, locally...
The price is AED 1,194
AED 2,158 total
includes taxes & fees
6 Oct - 7 Oct
Classic Maine Beach Cottage **** Fabulous location!
Updated Cottage - Steps to Pine Point Beach!
10.0 out of 10, Exceptional, (8)
"We have stayed here several times and really enjoy the cleanliness, and location to the beach."
Updated Cottage - Steps to Pine Point Beach!
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
10.0 out of 10, Exceptional, (26)
"We had my family with us on this special vacation with ages ranging from 2 years to 80 years old and every single one of us had a magical week. That is how I'd describe the Grey Goose beach house - magical! The attention to detail in the house was wonderful and the location can't be beat. We enjoyed the rocking chairs on the back porch and lounging on the upper deck with views of the ocean. We were lulled to sleep by the crashing of the waves, on chilly evenings the hot tub was fabulous, we...
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
9.8 out of 10, Exceptional, (49)
"Convenient to all that Old Orchard Beach has to offer. Great communication and offerings of beach chairs and beach towels. Wonderful time. Definitely recommend."
Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Quaint cottage intimately set on the rocky coast overlooking Casco Bay
9.8 out of 10, Exceptional, (22)
"Wonderful!"
Quaint cottage intimately set on the rocky coast overlooking Casco Bay
Charming Lakefront Cottage with Screened Porch, Firepit, Canoe & WiFi - 1 Dog OK
8.8 out of 10, Excellent, (6)
"I needed to find a rental where I could meet up with family from Mass and visit a sister in the Portland area as well as have some good adventures in the area before heading back to Florida. This was a good pick for what was needed - a cottage on Sebago Lake. We had a good time there."
Charming Lakefront Cottage with Screened Porch, Firepit, Canoe & WiFi - 1 Dog OK
Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit
9.8 out of 10, Exceptional, (48)
"We take an annual OOB trip for my daughters birthday, this is the first stay at this property, but it wont be the last! The location is perfect to the main strip and the beach, but far enough away to not be disrupted by the OOB night life! Highly recommend this property for anyone staying in OOB!"
Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit
Rose Cottage Oceanfront with Private Dock
10.0 out of 10, Exceptional, (12)
"Views were some of the best you could get,House was excellent needed for nothing."
Rose Cottage Oceanfront with Private Dock
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay
9.0 out of 10, Wonderful, (12)
"The cottage was furnished beautifully - very upbeat and modern. It was very clean, linens had been professionally laundered and sealed in bags. The kitchen was adorable and contained all appliances, utensils, dishes, glassware, and pots and pans to create a great meal. The water does have a sulfur oder, and we didn't realize until checking out - that the owner also supplied a dispenser for hot and cold spring water. Just remember to bring your our water! The staircase is winding and tight, and...
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay
Adorable waterfront gem with 2 kayaks, high-speed WiFi, full kitchen & dock
10.0 out of 10, Exceptional, (17)
"Lovely lakeside camp, great for kayaking (kayaks provided). Very clean and warm cabin. Hosts have created an experience that is very welcoming and “homey”."
Adorable waterfront gem with 2 kayaks, high-speed WiFi, full kitchen & dock
Private Contemporary Artist's Tree House on two acres with perennial gardens.
10.0 out of 10, Exceptional, (27)
"Fine time in Portland"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Quaint Cottage Just Steps From The Beach And The Saco River
10.0 out of 10, Exceptional, (12)
"My family had an amazing stay! This is our second time staying at the Avery’s property and from start to finish it was great! Scott was very helpful and always responded super quick with any questions I may have had! Great summer vacation for my family and we hope to do it again!! Thank you for a great week! "
Quaint Cottage Just Steps From The Beach And The Saco River
Classic Maine Beach Cottage! Steps to Pine Point Beach!
9.6 out of 10, Exceptional, (32)
"My wife and I had been hoping to get in a trip to Maine before the end of the season and this cottage was just what we needed. Pine Point is one of our favorite areas of Maine and we've been curious about these little cottages for years. It was fun to finally stay in one and we really enjoyed the bright but cozy interior. The location is great with easy access to the beach and all of Pine Point's restaurants. The cottage is also off the street, which helps with road noise."
Classic Maine Beach Cottage! Steps to Pine Point Beach!
The Little House - Gorgeous Views of Lowell's Cove and Casco Bay
10.0 out of 10, Exceptional, (11)
"Great location! We enjoyed our stay."
The Little House - Gorgeous Views of Lowell's Cove and Casco Bay
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
9.2 out of 10, Wonderful, (70)
"Very nice little cottage in quiet, private setting, but kitchen, bathroom and furnishings are all in poor condition. The shower and porch futon were gross - my wife wouldn't use either. This property really needs updating. Like other reviews, the wifi name/password info texted to me the day before was wrong. Luckily, someone left the correct info on the kitchen table."
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
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Other property types in Great Diamond Island

Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (87)
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Gorgeous ocean-front home with stunning beach views
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (118)
"This has been our fifth year staying in this condo and we are always super happy with the accommodations! Very clean and well taken care of, it’s an incredible spot.. live music you can listen to from the balcony and beautiful views, also so close to everything!"
The price is AED 808
AED 1,441 total
includes taxes & fees
3 Oct - 4 Oct
Oceanfront Condo! Spectacular Views From Private Large Balcony
Walk to Old Port ♦ West End Condo ♦ Parking
9.8 out of 10, Exceptional, (71)
"For the money we were happy with the Accommodations. The host was very helpful, a lot of towels were provided which was nice. Easy access and parking, quiet neighborhood."
The price is AED 993
AED 1,739 total
includes taxes & fees
29 Sep - 30 Sep
Walk to Old Port ♦ West End Condo ♦ 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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