Search Cottages in Chebeague Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Relax on the deck with a comfortable sofa set and enjoy the serene lake view.

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Stroll through the charming garden, featuring a tree with vibrant foliage and a wooden bench on the covered porch.

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (39)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Enjoy a peaceful retreat on this single-story home's deck, surrounded by lush trees and a clear sky.

Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

9.6 out of 10, Exceptional, (4)
"This was a gem, and the location was perfect for what we need. Very charming and such a comfortable bed"
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
WATERFRONT ON PETTENGILL POND
Escape to a serene retreat surrounded by lush greenery and a tranquil stream.

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
Little Miss Cottages
Stroll up to this charming home, featuring a cozy front porch surrounded by a lush garden and a beautifully maintained lawn.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (86)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Situated in a lush environment, this traditional house offers a serene setting with a sheltered front porch.

Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great property, great host, just as described."
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (2)
"Cute cabin in small quiet campground close to pool and short walk to downtown. The cabin itself was clean, cozy, and had everything we needed for a comfortable stay. Perfect for a small family getaway or a relaxing weekend."
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Large 2BD cottage 10 min to Pier & Beach Pets ok
Stroll up to the charming entrance, where a front porch invites you to relax.

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (33)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is HK$1,374
HK$2,421 total
includes taxes & fees
1 Sept - 2 Sept
Large 2BD cottage 10 min to Pier & Beach Pets ok
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Enjoy the ocean views from this deck overlooking the coastline.

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Situated in a suburban setting, this two-story home features a curved balcony and a mix of siding materials.

Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!

9.6 out of 10, Exceptional, (45)
"We enjoyed our visit"
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi
Outdoor dining

Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi

8.0 out of 10, Very good, (1)
"House was very clean with the exception of some dust/sand on floors, even though you could not see it walking on the floors in bare feet always felt that that maybe a good washing was needed. We just swept with the broom/vacuum and it was better. But one thing that really stood out when arriving is the cement stairs dug into the hill that you needed to go down to get to the house. So glad that there was a railing to hold onto because the stairs were not level at all. This posed a real threat to...
Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Relax on the deck with a tranquil view of the water, featuring a table, Adirondack chairs, and a shaded area.

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Relax on the dockside deck, surrounded by lush greenery and picturesque views of the marina.

'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!

10.0 out of 10, Exceptional, (12)
"Really enjoyed the house and location."
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Enjoy serene lakeside views from the deck, surrounded by blooming flowers and trees.

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Step outside to a serene, outdoor space surrounded by lush greenery and a beautiful tree with white blossoms.

Lilac Cottage - Near Georgetown Island - Midcoast Maine

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay at this property. Our dogs loved being able to chase eachother around the yard"
Lilac Cottage - Near Georgetown Island - Midcoast Maine
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Enjoy a serene garden oasis with lush plants, a hedge, and a small tree, surrounded by a stone wall and outdoor dining area.

15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit

9.8 out of 10, Exceptional, (51)
"Convenient to all that Old Orchard Beach has to offer. Great communication and offerings of beach chairs and beach towels. Wonderful time. Definitely recommend."
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
Relax on the waterfront deck with a barbecue grill and comfortable seating for two.

Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home

9.6 out of 10, Exceptional, (23)
"Very fun with beautiful views hoping to come back soon!"
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
2 bedroom cottage
Cozy living space with a kitchenette, sofa, dining table, and bench.

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Stunning two-story home with a charming front porch and covered entryway, set amidst a beautifully manicured lawn and a natural tree-lined backdrop.

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Waves Oceanfront Resort

Waves Oceanfront Resort

10/10 Excellent
"Great view, clean and friendly."
Evan 2-night trip
Posted 11 hours ago
Waves Oceanfront Resort

Frequently asked questions

Why book your cottage in Chebeague Island with Expedia?
We think that travelling should be a walk in the park, so if you're on the lookout for cottages in Chebeague Island at a great price, Expedia has got your back. Keep costs down and choose a low-cost option far from the downtown buzz, or book a luxury cottage to spoil your favourite people.
How can I find cheap cottages in Chebeague Island?
An excellent way to track down cheap cottages in Chebeague Island is with Expedia's convenient filter tool. Narrow your search by amenities, budget and star rating to access awesome bargains in a few clicks.