A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is ￥54,123
￥91,701 total
includes taxes & fees
Sep 28 - Sep 29
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A small house with a wooden deck and a porch.

2. •Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
10.0 out of 10, Exceptional, (1 review)
The price is ￥21,404
￥74,946 total
includes taxes & fees
Oct 1 - Oct 2
•Tranquil 2BR Summer Home•Steps to Private Beach•
A wooden deck with wicker furniture and a view of boats on the water.

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is ￥51,038
￥100,272 total
includes taxes & fees
Oct 3 - Oct 4
'Osprey Cottage' South Freeport Home on Casco Bay!
A wooden deck with wicker furniture and a view of boats on the water.

4. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is ￥61,276
￥95,257 total
includes taxes & fees
Sep 30 - Oct 1
'osprey Cottage' South Freeport Home on Casco Bay!
A two-story house with a front porch, a garage, and a well-maintained lawn.

5. 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 ￥22,973
￥43,268 total
includes taxes & fees
Oct 14 - Oct 15
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
A small house with a blue door, a deck with outdoor furniture, and a 'Welcome' sign.

6. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
The price is ￥19,082
￥119,786 total
includes taxes & fees
Sep 23 - Sep 24
Nautical View
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

7. 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 ￥24,628
￥59,141 total
includes taxes & fees
Sep 29 - Sep 30
Little Miss Cottages - One Bedroom Cottage
A single-story house with a covered porch, a front door, and a window.

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is ￥21,012
￥26,285 total
includes taxes & fees
Sep 19 - Sep 20
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.

9. 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.
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 front porch, a bench, and a well-maintained lawn.

10. 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 ￥27,768
￥48,867 total
includes taxes & fees
Sep 20 - Sep 21
Adorable 1 bedroom cabin only 50 ft from beach#1
A two-story house with a porch, surrounded by trees and a grassy yard.

11. 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 ￥46,539
￥86,406 total
includes taxes & fees
Sep 22 - Sep 23
Sweet comfy cottage on Small Point Road
A beach with people, a pier, and an American flag.

12. Updated 2 BD cottage. 10 min walk to Pier & Beach<br>- FREE parking<br>- 2 Queen beds and a futon<br>- Fast fiber Wifi<br>- ACs<br>- 2 smart TVs

Updated 2 BD cottage. 10 min walk to Pier & Beach<br>- FREE parking<br>- 2 Queen beds and a futon<br>- Fast fiber Wifi<br>- ACs<br>- 2 smart TVs
Old Orchard Beach
8.2 out of 10, Very good, (27 reviews)
"Even though the property was small it was spacious for two people especially my husband and I we had an awesome awesome week there the host was unbelievably kind the woman Kathy that clean the unit was exceptional and very very nice the neighborhood was peaceful and it was very convenient to the pier and all the shops definitely will be staying there from now on every year it was awesome"
United States
Catherine
Updated 2 BD cottage. 10 min walk to Pier & Beach<br>- FREE parking<br>- 2 Queen beds and a futon<br>- Fast fiber Wifi<br>- ACs<br>- 2 smart TVs
A pier with a building on stilts over the beach.

13. 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 ￥27,768
￥48,867 total
includes taxes & fees
Oct 12 - Oct 13
beautiful 1 bedroom cabin only 50 ft from beach
A two-story house with a garage and a covered porch.

14. 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 ￥15,823
￥42,069 total
includes taxes & fees
Sep 23 - Sep 24
1 Mi to Maine Street! Mcm-style Home in Brunswick
A wooden pier with multiple pillars extending into the water.

15. 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 ￥27,768
￥48,867 total
includes taxes & fees
Sep 20 - Sep 21
Attractive 1 bedroom cabin only 50 ft from beach
A rustic building with a pond, stone pathway, and flower beds.

16. 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 ￥27,768
￥48,698 total
includes taxes & fees
Sep 23 - Sep 24
Cheerful 1 bedroom cottage only 50ft from beach
A pier extending into calm waters with a building at the end.

17. 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 ￥27,768
￥48,698 total
includes taxes & fees
Sep 21 - Sep 22
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A room with a ceiling fan, a dining table with chairs, a sofa, and a window with blinds.

18. Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)

Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)
Old Orchard Beach
9.0 out of 10, Wonderful, (45 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)
An aerial view of a residential area with numbered houses, a central patio with outdoor furniture, and surrounding greenery.

19. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is ￥27,768
￥48,867 total
includes taxes & fees
Sep 20 - Sep 21
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.

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

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
5.4 out of 10, (3 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 ￥27,174
￥67,436 total
includes taxes & fees
Oct 15 - Oct 16
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"The room was great. The property was nicely kept. However, what stands out the most is the integrity and helpfulness of the staff. I accidentally left my wedding ring in the room and the housekeeping staff found it and notified me. Honesty at its best. Then, a woman named Lisa in accounting went above and beyond to take the ring to Fed Ex and send it to our next stop on our trip. I can’t say enough how grateful I am to Lisa and the housekeeping staff for doing this. It reflects highly on the hotel. They are just awesome!"
Garnett 1-night trip
Posted 11 hours ago
Fireside Inn & Suites Portland

Find out more about Great Diamond Island

Great Diamond Island Cottages information

Number of reviews
265
Accommodation
158 Cottages
Lowest Price
￥26,285
Highest Price
￥119,786

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