A wooden pier leading to a marina with boats docked.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chebeague Island cottages

A two-story house with a garage and a covered porch.

1. 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
Aug 25 - Aug 26
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.

2. 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, (16 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$818 nightly
The price is $892
Sep 2 - Sep 3
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.

3. 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.
$514 nightly
The price is $560
Sep 1 - Sep 2
Total with taxes and fees
Sweet comfy cottage on Small Point Road

4. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$176 nightly
The price is $192
Aug 23 - Aug 24
Total with taxes and fees
Charming Rustic Cottage
A beachfront property with multiple buildings, including a cottage-style house and a larger building with a balcony. There are several white lounge chairs arranged on the sandy beach in front of the buildings.

5. 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.
$895 nightly
The price is $968
Sep 7 - Sep 8
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
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, (15 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
$368 nightly
The price is $401
Sep 1 - Sep 2
Total with taxes and fees
Little Miss Cottages - One Bedroom 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.

7. 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.
$358 nightly
The price is $362
Sep 15 - Sep 16
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 pier with a building on stilts over the beach.

8. 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.
$381 nightly
The price is $415
Sep 22 - Sep 23
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
A room with a ceiling fan, a dining table with chairs, a sofa, and a window with blinds.

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)

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.
$385 nightly
The price is $390
Sep 7 - Sep 8
Total with taxes and fees
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)
A beach with people, a pier, and an American flag.

10. 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
8.0 out of 10, Very Good, (25 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
$365 nightly
The price is $369
Sep 7 - Sep 8
Total with taxes and fees
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 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, (8 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$384 nightly
The price is $419
Sep 22 - Sep 23
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
A pier extending into calm waters with a building at the end.

12. 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.
$393 nightly
The price is $428
Sep 22 - Sep 23
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A wooden pier with multiple pillars extending into the water.

13. 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.
$425 nightly
The price is $463
Sep 7 - Sep 8
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
A rustic building with a pond, stone pathway, and flower beds.

14. 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.
$425 nightly
The price is $463
Sep 7 - Sep 8
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
A white wooden house with a white picket fence, a small porch, and a window with shutters.

15. 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.
$466 nightly
The price is $508
Sep 22 - Sep 23
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the 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
$428 nightly
The price is $467
Sep 1 - Sep 2
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.
$527 nightly
The price is $575
Aug 25 - Aug 26
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"The shower needs to be fixed."
Pablo 4-night trip
Posted less than an hour ago
Clarion Pointe South Portland

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
136
Accommodation
207 Cottages
Lowest Price
$192
Highest Price
$968

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