A wooden pier leading to a marina with boats docked.

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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 Chebeague Island cottages

Exterior

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)
$483 nightly
The price is $527
Oct 1 - Oct 2
Total with taxes and fees
•Tranquil 2BR Summer Home•Steps to Private Beach•
House (2 Bedrooms) | Interior

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
Exterior

3. 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.
$511 nightly
The price is $557
Sep 22 - Sep 23
Total with taxes and fees
Sweet comfy cottage on Small Point Road
Exterior

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, (19 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$522 nightly
The price is $569
Sep 28 - Sep 29
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

5. 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.
$334 nightly
The price is $364
Sep 21 - Sep 22
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

6. 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.
$254 nightly
The price is $277
Oct 14 - Oct 15
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

7. 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.
$264 nightly
The price is $288
Sep 21 - Sep 22
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Exterior

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$145 nightly
The price is $158
Sep 25 - Sep 26
Total with taxes and fees
Charming Rustic Cottage
Beach nearby

9. 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.
$264 nightly
The price is $288
Sep 21 - Sep 22
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

10. 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 21 - Sep 22
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Property grounds

11. 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.
$264 nightly
The price is $288
Sep 24 - Sep 25
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Beach nearby

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.
$260 nightly
The price is $283
Sep 24 - Sep 25
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

13. 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.
$329 nightly
The price is $359
Oct 13 - Oct 14
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
Exterior

14. 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
Sep 30 - Oct 1
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

15. 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.
$408 nightly
The price is $444
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

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

8/10 Good
"Room for two nights was very expensive but more affordable than the alternatives in Portland. Was just in town for two nights and was out with friends the whole time and didn’t use any amenities, but the property was clean and check in a breeze. Like others, I found the $10 parking surcharge a bit excessive for a property with plenty of onsight parking. Lastly, I made my reservations about a month before arrival, but it was impossible to call the hotel and confirm the reservation a day before arrival. Frustrating, but I’d stay here again…"
Peter 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
165
Accommodation
207 Cottages
Lowest Price
$158
Highest Price
$569

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