A calm sea with a sailboat and rocky coastline.

Search Great Diamond Island Cottage Rentals from CA $352

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Great Diamond Island cottages

Exterior

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, (17 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
The price is CA $641
CA $1,024 total
includes taxes & fees
Sep 2 - Sep 3
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

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 CA $229
CA $715 total
includes taxes & fees
Sep 1 - Sep 2
•Tranquil 2BR Summer Home•Steps to Private Beach•
Exterior

3. Cottages by the Sea #1 by Bayley Vacation Rentals

Cottages by the Sea #1 by Bayley Vacation Rentals
Surfside
9.8 out of 10, Exceptional, (9 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
United States
Matthew J.
The price is CA $292
CA $1,335 total
includes taxes & fees
Sep 7 - Sep 8
Cottages by the Sea #1 by Bayley Vacation Rentals
Exterior

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (17 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is CA $206
CA $514 total
includes taxes & fees
Sep 1 - Sep 2
Little Miss Cottages - One Bedroom Cottage
Exterior

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, (87 reviews)
"Perfect getaway cottage for my husband & me & our 2 small dogs. And a fenced-in yard!"
United States
Margaret K.
The price is CA $285
CA $484 total
includes taxes & fees
Sep 3 - Sep 4
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

6. 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 CA $137
CA $393 total
includes taxes & fees
Sep 22 - Sep 23
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Exterior

7. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
The price is CA $301
CA $1,236 total
includes taxes & fees
Sep 4 - Sep 5
Nautical View
Property grounds

8. 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 CA $277
CA $473 total
includes taxes & fees
Sep 1 - Sep 2
Cheerful 1 bedroom cottage only 50ft from beach
House (2 Bedrooms) | Interior

9. 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 CA $142
CA $377 total
includes taxes & fees
Sep 23 - Sep 24
1 Mi to Maine Street! Mcm-style Home in Brunswick
Exterior

10. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is CA $291
CA $352 total
includes taxes & fees
Sep 6 - Sep 7
Charming Rustic Cottage
Exterior

11. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 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 CA $417
CA $776 total
includes taxes & fees
Sep 1 - Sep 2
Sweet comfy cottage on Small Point Road
Interior

12. 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, (43 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
The price is CA $139
CA $454 total
includes taxes & fees
Sep 8 - Sep 9
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)
Beach

13. 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, (26 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
The price is CA $158
CA $416 total
includes taxes & fees
Sep 7 - Sep 8
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
Beach nearby

14. 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 CA $277
CA $473 total
includes taxes & fees
Aug 31 - Sep 1
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

15. 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, (8 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is CA $277
CA $473 total
includes taxes & fees
Aug 31 - Sep 1
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach nearby

16. 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 CA $277
CA $473 total
includes taxes & fees
Aug 31 - Sep 1
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

17. 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 CA $237
CA $597 total
includes taxes & fees
Sep 1 - Sep 2
Little Miss Cottages - Two Bedroom Cottage Suite - 9
Beach nearby

18. 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
9.6 out of 10, Exceptional, (5 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
The price is CA $277
CA $473 total
includes taxes & fees
Aug 31 - Sep 1
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior

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 CA $277
CA $473 total
includes taxes & fees
Aug 31 - Sep 1
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

20. 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 CA $406
CA $668 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 2 bedroom cabin, 50ft from the beach
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Diamond Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Helpful staff and the shuttle to/from airport and back and forth from downtown was really great."
DeeDee 4-night trip
Posted 3 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Great Diamond Island

Great Diamond Island Cottages information

Number of reviews
262
Accommodation
161 Cottages
Lowest Price
CA $352
Highest Price
CA $1,335

Frequently asked questions

Why book your cottage in Great Diamond Island with Expedia?
Booking a cottage in Great Diamond Island is as simple as clicking on your travel dates and selecting an ideal place for outdoor relaxation and recreation. From luxurious retreats to inexpensive stays and cottages that come with amenities like laundry facilities, Expedia has something for all styles and tastes. As for terrific deals? We've got them too!
How can I find cheap cottages in Great Diamond Island?
Expedia can help you locate cheap cottages in Great Diamond Island. To book a fantastic stay in a couple of quick clicks, try out our handy filter tool to refine your search by amenities, star rating and budget.

Explore a world of travel with Expedia