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)
$588 nightly
The price is $641
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. 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)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$681 nightly
The price is $742
Sep 2 - Sep 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
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.
$514 nightly
The price is $560
Sep 7 - Sep 8
Total with taxes and fees
Sweet comfy cottage on Small Point Road
Exterior

5. 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.
$339 nightly
The price is $369
Sep 2 - Sep 3
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

6. 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.
$887 nightly
The price is $959
Sep 7 - Sep 8
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
Exterior

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, (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.
$287 nightly
The price is $312
Sep 2 - Sep 3
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Interior

8. 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.
$332 nightly
The price is $336
Sep 29 - Sep 30
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)
Property grounds

9. 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 2 - Sep 3
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

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.
$412 nightly
The price is $449
Sep 8 - Sep 9
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Exterior

11. 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
Room

12. 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.
$280 nightly
The price is $283
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
Beach

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.
$290 nightly
The price is $316
Sep 2 - Sep 3
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

14. 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 2 - Sep 3
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach

15. 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.
$290 nightly
The price is $316
Sep 2 - Sep 3
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Beach

16. 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.
$290 nightly
The price is $316
Sep 2 - Sep 3
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Beach

17. 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
$288 nightly
The price is $291
Sep 8 - Sep 9
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
Exterior

18. 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.
$379 nightly
The price is $413
Sep 2 - Sep 3
Total with taxes and fees
Little Miss Cottages - Two Bedroom Cottage Suite - 9
Exterior

19. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$290 nightly
The price is $316
Sep 2 - Sep 3
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

20. 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.
$399 nightly
The price is $435
Sep 20 - Sep 21
Total with taxes and fees
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

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

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

10/10 Excellent
"Came to town for one night to attend show @ Thompson's Point. Hotel was clean and convenient . Staff friendly and helpful. Definitely would stay again"
MaryAnn 1-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
Accommodation
207 Cottages
Lowest Price
$271
Highest Price
$614

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