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Compare 145 Cottages in Chebeague Island with updated reviews, rates, and availability.

Private Contemporary Artist's Tree House on two acres with perennial gardens.
The floating two story private addition extends into the apple trees.

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

10.0 out of 10, Exceptional, (31)
"Very homey, very clean, comfortable bed. All we needed during our stay was procedez. The host was extremely responsive and courteous. We will like to visit again and I would stay here again."
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Charming cottage short walk to beach!
1

Charming cottage short walk to beach!

9.4 out of 10, Exceptional, (26)
"We had a great time on our recent stay here. short walk to the beach, quiet neighborhood. This home was fully stocked with all the amenities and truly felt like our home away from home. Check in/out was seamless and there was great communication the the host. If we ever plan to travel to the area again, we would definately stay here once more. "
Charming cottage short walk to beach!
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Open concept Living/Dining/Kitchen

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

9.8 out of 10, Exceptional, (49)
"Convenient to all that Old Orchard Beach has to offer. Great communication and offerings of beach chairs and beach towels. Wonderful time. Definitely recommend."
Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Morning Sunrise.

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

9.8 out of 10, Exceptional, (26)
"Exceptional views. The cottage is clean and well furnished with thoughtful accessories. There are many places of interest in the area."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit
Living area

Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit

9.8 out of 10, Exceptional, (48)
"the location was perfect. Close enough to walk to everything, but far enough to not be noisy from the crowds. The place was very clean and had all of the amenities we needed. I would 100% stay here again. The property manager was easy to contact and answered every question or concern in a very quick manner and was very kind. Highly recommend this property"
Great Location! Walk to Beach/Pier in 5 minutes-Cottage Sleeps 6;12 w/front unit
Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.
Park here in front of the white dock box that has 4 chairs and an umbrella.

Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.

10.0 out of 10, Exceptional, (80)
"We chose this property for our first trip to Maine and our honeymoon. We were amazed by all the property had to offer and it looked even more beautiful in person! Plus, the bed was unbelievably comfortable. The hosts were easy to communicate with and it was clear that they valued our experience. The hosts left us personalized goodies and took us on a complimentary boat tour. We have never had such a good rental experience. Thank you!"
Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

10.0 out of 10, Exceptional, (1)
"Boomfish Cottage is a cozy place with everything you could need . It was clean , comfy and serene . It provided the perfect calm for us during a weekend long family wedding at nearby Caswell Flower Farm . It was also easy access for an older person ( me) as well as small children and my little ShihTzu rescue dogs . My granddaughters came by and loved catching minnows in the still warm lake. Extra bonus was enjoying the peak foliage at the lake . Eric , the property manager was very communicative...
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Large 2BD cottage 10 min to Pier & Beach Pets ok
Room

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

9.2 out of 10, Wonderful, (25)
"We had a wonderful visit to OOB to finish off our summer. The cottage is a quick walk to the beach and pier. It was very clean and comfortable for the four of us to relax and recharge in between swimming, playing mini-gold, and enjoying the amusement park."
The price is AED 441
AED 893 total
includes taxes & fees
9 Dec - 10 Dec
Large 2BD cottage 10 min to Pier & Beach Pets ok
Little Miss Cottages
Exterior

Little Miss Cottages

2.5 star property
8.4 out of 10, Very Good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
Little Miss Cottages
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Path to the beach

Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals

10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Exterior

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

9.6 out of 10, Exceptional, (38)
"What a wonderful stay. The views were absolutely amazing. Kitchen well equipped. We bought live lobsters just $10 a lb from Hannafords (try also the French baguette) just 12 min drive and cooked them, clams and corn all in the steamer provided. Lounge seating very comfortable. Cooks corner area has everything incl Walmart superstore. David was a wonderful host. Could not speak too highly of him. He came out late at night when I could not work something out."
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay

Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay

9.2 out of 10, Wonderful, (15)
"Great cottage! Like stayimg at grandma's house with wifi!. Rely nice location with ocean view and much to see and do in area. Will stay again."
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay
Charming 3BR, 1.5BA beachfront cottage with multi-level decks

Charming 3BR, 1.5BA beachfront cottage with multi-level decks

9.2 out of 10, Wonderful, (31)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Classic Old Orchard Beach Cottage One Block from the Beach
Living area

Classic Old Orchard Beach Cottage One Block from the Beach

8.8 out of 10, Excellent, (5)
"Front and back porch were great. Sheets and towels included, very convenient. Fireplace in the middle of the place was a bit awkward but overall a nice setup. "
Classic Old Orchard Beach Cottage One Block from the Beach
Lakefront cabin with shared firepit & access to Sebago Lake

Lakefront cabin with shared firepit & access to Sebago Lake

8.0 out of 10, Very Good, (10)
"very nice!"
Lakefront cabin with shared firepit & access to Sebago Lake
Classic Maine Beach Cottage **** Fabulous location!
Vibrant active local boating community

Classic Maine Beach Cottage **** Fabulous location!

9.2 out of 10, Wonderful, (24)
"Comfortable cottage with plenty of room. Very pleasant living space. We found it very convenient to the things we like to do, places we like to go. We would certainly come back"
The price is AED 1,194
AED 2,166 total
includes taxes & fees
1 Dec - 2 Dec
Classic Maine Beach Cottage **** Fabulous location!
Updated Long Island Maine Cottage
Interior

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Chaz' Long Island house. It is open and airy and maintains its 100 year old charm even as it's been updated. It sits in a great, grassy yard with plenty of bright light and has a terrific, large deck on the front. The golf cart ride to all beaches is short and lovely!"
Updated Long Island Maine Cottage
The Outlet House, Comfortable Cottage
Interior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (35)
"Nice clean quiet place but close to a lot of things."
The Outlet House, Comfortable Cottage
*****Charming Cottage 5 min walk to beach & 8 min. walk to pier !!!
Seaglass Cottage, 28 Central Park Avenue, Old Orchard Beach, ME.

*****Charming Cottage 5 min walk to beach & 8 min. walk to pier !!!

10.0 out of 10, Exceptional, (74)
"We were so pleased with our stay! We have stayed 4 times before at OOB with the kids. This time this house waa perfect. Loved all the decorations. Every detail is thought through."
*****Charming Cottage 5 min walk to beach & 8 min. walk to pier !!!
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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Other property types in Chebeague Island

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Beach

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Gorgeous ocean-front home with stunning beach views

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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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