A wooden pier leading to a marina with boats docked.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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)
$551 nightly
The price is $600
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
Outdoor dining

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
$593 nightly
The price is $646
Sep 30 - Oct 1
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
Exterior

4. 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.
$512 nightly
The price is $558
Sep 7 - Sep 8
Total with taxes and fees
Sweet comfy cottage on Small Point Road
Room

5. 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.
$279 nightly
The price is $282
Sep 29 - Sep 30
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
Exterior

6. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.0 out of 10, Wonderful, (18 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.
$365 nightly
The price is $397
Sep 28 - Sep 29
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

7. 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)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$802 nightly
The price is $874
Oct 2 - Oct 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

8. 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.
$894 nightly
The price is $967
Sep 7 - Sep 8
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
Exterior

9. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$155 nightly
The price is $169
Sep 12 - Sep 13
Total with taxes and fees
Charming Rustic Cottage
Exterior

10. 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, (89 reviews)
"Our group of four golf spouses spent the weekend at this lovely vacation home. Location was fantastic - very convenient to multiple golf courses. House was impeccably decorated and nicely appointed. We will be back!"
United States
Susan V.
$326 nightly
The price is $355
Sep 22 - Sep 23
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

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.
$290 nightly
The price is $316
Sep 13 - Sep 14
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Cottage (2 Bedrooms) | Interior

12. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
$579 nightly
The price is $614
Sep 30 - Oct 1
Total with taxes and fees
'osprey Cottage' South Freeport Home on Casco Bay!
Exterior

13. 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.
$411 nightly
The price is $448
Sep 8 - Sep 9
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Beach

14. 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
$300 nightly
The price is $304
Sep 9 - Sep 10
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
Beach

15. 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.
$288 nightly
The price is $314
Sep 14 - Sep 15
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach

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.
$288 nightly
The price is $314
Sep 17 - Sep 18
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Beach

17. 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.
$288 nightly
The price is $314
Sep 20 - Sep 21
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Property grounds

18. 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.
$290 nightly
The price is $316
Sep 13 - Sep 14
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Interior

19. 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, (44 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
$354 nightly
The price is $358
Oct 1 - Oct 2
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)
Exterior

20. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$288 nightly
The price is $314
Sep 16 - Sep 17
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from 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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Staff was very friendly and courteous."
Brenda 1-night trip
Posted 4 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
247
Accommodation
207 Cottages
Lowest Price
$169
Highest Price
$967

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