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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 Chebeague Island cottages

A small house with a wooden deck and a porch.

1. •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 $213
CA $700 total
includes taxes & fees
Oct 1 - Oct 2
•Tranquil 2BR Summer Home•Steps to Private Beach•
A two-story house with a garage and a covered porch.

2. 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 $144
CA $384 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! Mcm-style Home in Brunswick
A two-story house with a gabled roof and a front porch.

3. 3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"Super clean and spacious in a walkable area. "
United States
Nell F.
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
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.

4. 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, (20 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is CA $469
CA $825 total
includes taxes & fees
Sep 28 - Sep 29
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A two-story house with a porch, surrounded by trees and a grassy yard.

5. 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 CA $424
CA $792 total
includes taxes & fees
Oct 4 - Oct 5
Sweet comfy cottage on Small Point Road
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

6. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (23 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 CA $133
CA $430 total
includes taxes & fees
Sep 29 - Sep 30
Little Miss Cottages - One Bedroom Cottage
A two-story house with a front porch, a garage, and a well-maintained lawn.

7. 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, (92 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 CA $197
CA $378 total
includes taxes & fees
Oct 6 - Oct 7
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
A wooden pier with multiple pillars extending into the water.

8. 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 $225
CA $413 total
includes taxes & fees
Oct 5 - Oct 6
Attractive 1 bedroom cabin only 50 ft from beach
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.
The price is CA $171
CA $438 total
includes taxes & fees
Oct 28 - Oct 29
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
A small, single-story house with a number '20' on the front, a front door, and a small porch with steps leading up to it.

10. Soothing 2-bedroom cottage with Sauna in Old Orchard Beach

Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Would stay again!!"
United States
Jay T.
The price is CA $351
CA $657 total
includes taxes & fees
Oct 18 - Oct 19
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

11. 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 CA $192
CA $549 total
includes taxes & fees
Sep 28 - Sep 29
Little Miss Cottages - Two Bedroom Cottage Suite - 9
A pier with a building on stilts over the beach.

12. 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 $225
CA $413 total
includes taxes & fees
Sep 30 - Oct 1
beautiful 1 bedroom cabin only 50 ft from beach
A two-story house with a front porch, a bench, and a well-maintained lawn.

13. 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 CA $211
CA $395 total
includes taxes & fees
Sep 29 - Sep 30
Adorable 1 bedroom cabin only 50 ft from beach#1
A pier extending into calm waters with a building at the end.

14. 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 CA $225
CA $413 total
includes taxes & fees
Sep 30 - Oct 1
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A rustic building with a pond, stone pathway, and flower beds.

15. 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 $211
CA $395 total
includes taxes & fees
Sep 29 - Sep 30
Cheerful 1 bedroom cottage only 50ft from beach
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
Attractive 1 bedroom cabin only 50 ft from beach
A white wooden house with a white picket fence, a small porch, and a window with shutters.

17. 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 $310
CA $563 total
includes taxes & fees
Oct 18 - Oct 19
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.
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Top Chebeague Island Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"The front desk staff members were friendly and helpful. The location was convenient for air travel using PWM. Our room was clean, but the ceiling in the bathroom needs attention and may have an issue with mold."
Paulette 1-night trip
Posted 1 hour ago
Clarion Pointe South Portland

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
182
Accommodation
207 Cottages
Lowest Price
CA $378
Highest Price
CA $825

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