A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Great Diamond Island cottages

A two-story house with a white exterior and a black base. There is a white staircase leading to the front door, surrounded by lush greenery and flowering plants.

1. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (19 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is ￥52,210
￥91,202 total
includes taxes & fees
Sep 28 - Sep 29
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A small house with a blue door, a deck with outdoor furniture, and a 'Welcome' sign.

2. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
Nautical View
A two-story house with a front porch, a garage, and a well-maintained lawn.

3. 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, (91 reviews)
"Great, pet-friendly spot! Walkable to the beach, places to eat, etc. Loved the space (indoor and outdoor) to spread out a bit."
United States
Blake S.
The price is ￥23,597
￥44,068 total
includes taxes & fees
Oct 14 - Oct 15
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (21 reviews)
"It was very clean and it’s pet friendly. The host went above and beyond and was truly friendly while doing so. A great location and quiet at this time of year. The bed was very comfortable. The shower nice and hot. I would rent that seaside shanty again. "
United States
Lynne B.
The price is ￥20,727
￥54,829 total
includes taxes & fees
Sep 23 - Sep 24
Little Miss Cottages - One Bedroom Cottage
A wooden pier with multiple pillars extending into the water.

5. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great place! Loved being on the end so we only had one neighbor. No crazy list of things to do at check out was much appreciated."
United States
Mandy H.
The price is ￥25,012
￥45,096 total
includes taxes & fees
Sep 23 - Sep 24
Attractive 1 bedroom cabin only 50 ft from beach
A single-story house with a covered porch, a front door, and a window.

6. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is ￥18,004
￥23,054 total
includes taxes & fees
Sep 25 - Sep 26
Charming Rustic Cottage
A room with a bed, a round wooden table, a ceiling fan, a TV on the wall, and a door leading to another room.

7. Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs

Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Was as advertised."
United States
Andrew H.
The price is ￥25,107
￥56,077 total
includes taxes & fees
Oct 23 - Oct 24
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
A two-story house with a garage and a covered porch.

8. 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
The price is ￥16,046
￥42,661 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! Mcm-style Home in Brunswick
A two-story house with a front porch, a bench, and a well-maintained lawn.

9. Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
9.8 out of 10, Exceptional, (9 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is ￥25,012
￥45,096 total
includes taxes & fees
Sep 23 - Sep 24
Adorable 1 bedroom cabin only 50 ft from beach#1
A rustic building with a pond, stone pathway, and flower beds.

10. Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (5 reviews)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
The price is ￥25,012
￥43,895 total
includes taxes & fees
Sep 24 - Sep 25
Cheerful 1 bedroom cottage only 50ft from beach
A pier with a building on stilts over the beach.

11. beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Being so close to the water was great. Place was a little smaller than we typically get but sufficient and was very clean. The owner was great to communicate with and quick to respond to questions. We particularly liked the shaded patio area in front."
United States
Allan S.
The price is ￥25,012
￥43,895 total
includes taxes & fees
Sep 24 - Sep 25
beautiful 1 bedroom cabin only 50 ft from beach
A two-story house with a porch, surrounded by trees and a grassy yard.

12. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is ￥47,193
￥87,106 total
includes taxes & fees
Sep 23 - Sep 24
Sweet comfy cottage on Small Point Road

13. Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Biddeford Pool
9.4 out of 10, Exceptional, (60 reviews)
"We love this place. Our dogs enjoy coming."
United States
amy b.
The price is ￥51,126
￥63,447 total
includes taxes & fees
Oct 1 - Oct 2
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
A white wooden house with a white picket fence, a small porch, and a window with shutters.

14. Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
8.8 out of 10, Excellent, (3 reviews)
"Clean room, friendly host, a nice part of the beach that you walk out to."
United States
Beverley R.
The price is ￥29,732
￥54,184 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 2 bedroom cabin, 50ft from the beach
A pier extending into calm waters with a building at the end.

15. Cozy one bedroom cottage, 50 feet from the beach in OOB.

Cozy one bedroom cottage, 50 feet from the beach in OOB.
Old Orchard Beach
9.8 out of 10, Exceptional, (6 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
The price is ￥25,012
￥45,267 total
includes taxes & fees
Sep 30 - Oct 1
Cozy one bedroom cottage, 50 feet from the beach in OOB.
An aerial view of a residential area with numbered houses, a central patio with outdoor furniture, and surrounding greenery.

16. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is ￥25,012
￥45,267 total
includes taxes & fees
Oct 7 - Oct 8
Attractive 1 bedroom cabin only 50 ft from beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

17. Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
6.6 out of 10, (4 reviews)
"WiFi and tv was spotty on a good day and non existent towards the end of our stay. If we were to go again I wouldn’t want to stay in suite 9. Some of the other cottages were a little more secluded and had a deck."
United States
Ralph B.
The price is ￥29,222
￥70,261 total
includes taxes & fees
Oct 20 - Oct 21
Little Miss Cottages - Two Bedroom Cottage Suite - 9
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 Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Very helpful staff! The room we had reserved for us was on the main floor & a bit loud so the front desk gave us the option to go higher up for reduced noise. The nooks on each floor with free coffee, water, pastries, yogurts, and snacks was a wonderful touch. The hotel is an amazing location & close to everything!"
Forgotten 2-night trip
Posted less than an hour ago
Portland Harbor Hotel

Find out more about Great Diamond Island

Great Diamond Island Cottages information

Number of reviews
254
Accommodation
158 Cottages
Lowest Price
￥23,054
Highest Price
￥91,202

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