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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chebeague Island cottages

Exterior

1. 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
Aug 31 - Sep 1
Total with taxes and fees
Sweet comfy cottage on Small Point Road
Exterior

2. •Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
$529 nightly
The price is $577
Sep 1 - Sep 2
Total with taxes and fees
•Tranquil 2BR Summer Home•Steps to Private Beach•
House (2 Bedrooms) | Interior

3. 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
1 Mi to Maine Street! Mcm-style Home in Brunswick
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, (16 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$698 nightly
The price is $761
Sep 2 - Sep 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

5. Cottages By The Sea #2 by Bayley Vacation Rentals

Cottages By The Sea #2 by Bayley Vacation Rentals
Surfside
10.0 out of 10, Exceptional, (2 reviews)
"Perfect little getaway."
United States
Tish L.
Cottages By The Sea #2 by Bayley Vacation Rentals
Exterior

6. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$193 nightly
The price is $210
Sep 12 - Sep 13
Total with taxes and fees
Charming Rustic Cottage
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
9.6 out of 10, Exceptional, (85 reviews)
"Perfect getaway cottage for my husband & me & our 2 small dogs. And a fenced-in yard!"
United States
Margaret K.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

8. 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.
$390 nightly
The price is $425
Sep 1 - Sep 2
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Interior

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 8 - Sep 9
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

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.
$409 nightly
The price is $446
Sep 8 - Sep 9
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Beach nearby

11. 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.
$402 nightly
The price is $438
Sep 15 - Sep 16
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

12. 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.
$896 nightly
The price is $969
Sep 7 - Sep 8
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
Beach

13. 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, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
$361 nightly
The price is $365
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
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

14. 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.
$382 nightly
The price is $386
Sep 13 - Sep 14
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

15. 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.
$415 nightly
The price is $452
Sep 15 - Sep 16
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Property grounds

16. 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.
$432 nightly
The price is $471
Sep 7 - Sep 8
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

17. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$465 nightly
The price is $507
Sep 15 - Sep 16
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

18. 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.
$409 nightly
The price is $446
Sep 15 - Sep 16
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

19. 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.
$425 nightly
The price is $463
Sep 15 - Sep 16
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
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.
$465 nightly
The price is $507
Sep 8 - Sep 9
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"John at front desk went above and beyond for us. The free shuttle is a major plus. I wish the restaurant had been open but it was closed the days we were there"
Pastor Doug 1-night trip
Posted 2 hours ago
Clarion Hotel Portland Airport ME

Find out more about Chebeague Island

Chebeague Island Cottages information

Number of reviews
12,164
Accommodation
207 Cottages
Lowest Price
$97
Highest Price
$251

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