A wooden pier leading to a marina with boats docked.

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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)
$469 nightly
The price is $511
Oct 1 - Oct 2
Total with taxes and fees
•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
$249 nightly
The price is $271
Sep 23 - Sep 24
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
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.

3. 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.
$532 nightly
The price is $580
Sep 28 - Sep 29
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A two-story house with a porch, surrounded by trees and a grassy yard.

4. 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.
$508 nightly
The price is $554
Sep 23 - Sep 24
Total with taxes and fees
Sweet comfy cottage on Small Point Road
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.
$257 nightly
The price is $280
Oct 14 - Oct 15
Total with taxes and fees
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.

6. 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.
$320 nightly
The price is $349
Sep 23 - Sep 24
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
A wooden pier with multiple pillars extending into the water.

7. 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.
$263 nightly
The price is $287
Sep 23 - Sep 24
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
A single-story house with a covered porch, a front door, and a window.

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$134 nightly
The price is $147
Sep 25 - Sep 26
Total with taxes and fees
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.
$353 nightly
The price is $356
Oct 23 - Oct 24
Total with taxes and fees
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.
$432 nightly
The price is $471
Oct 18 - Oct 19
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
A two-story house with a front porch, a bench, and a well-maintained lawn.

11. 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.
$263 nightly
The price is $287
Sep 23 - Sep 24
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
A rustic building with a pond, stone pathway, and flower beds.

12. 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.
$254 nightly
The price is $277
Sep 24 - Sep 25
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
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.
$254 nightly
The price is $277
Sep 24 - Sep 25
Total with taxes and fees
beautiful 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.

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.
$317 nightly
The price is $346
Sep 23 - Sep 24
Total with taxes and fees
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.
$264 nightly
The price is $288
Sep 30 - Oct 1
Total with taxes and fees
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
$264 nightly
The price is $288
Oct 7 - Oct 8
Total with taxes and fees
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
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.
$410 nightly
The price is $447
Oct 20 - Oct 21
Total with taxes and fees
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 Chebeague Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Great hotel with delicious breakfast."
Anna 1-night trip
Posted 6 hours ago
Portland Harbor Hotel

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
Accommodation
207 Cottages
Lowest Price
$271
Highest Price
$271

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