Holiday Homes in Chebeague Island

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Featured Holiday Homes in Chebeague Island

Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk
9.2 out of 10, Wonderful, (17)
"The place was clean, beautiful, and centrally located to shops, restaurants and bars. It was tucked away and quiet right on the lake. Would highly recommend!"
Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk
Seaside Splendor: 4BR House Close to Beach & Pier
9.6 out of 10, Exceptional, (12)
"This property worked out great for 4 of my employees to stay while working on a video surveillance installation at a local car dealership."
Seaside Splendor: 4BR House Close to Beach & Pier
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Orchard Beach Elegance: Spacious Yard & Patio
10.0 out of 10, Exceptional, (10)
"We rented this property for our 6 year anniversary and it was even better than we were expecting! Great location with the perfect amount of privacy. Highly recommend this location for families and couples! "
Orchard Beach Elegance: Spacious Yard & Patio
Contemporary Comfort: Game Room & Portland Access
Contemporary Comfort: Game Room & Portland Access
One queen bed unit 16 at Belkis beach motel
6.8 out of 10, (3)
"We have stayed here twice and it work perfect for us. Close to the beach and convenient. Staff are friendly and accommodating. Will stay here again."
One queen bed unit 16 at Belkis beach motel
Full sized home
9.6 out of 10, Exceptional, (4)
"Great place to stay. Host was helpful and responsive."
The price is NZ$561
includes taxes & fees
2 Jun - 3 Jun
Full sized home
Old Orchard Beach Getaway| 2BD Cottage
10.0 out of 10, Exceptional, (3)
"My aunt and I were looking for a central location for shopping in and around Old Orchard Beach area. Perfect location. Quiet and clean. Host was very quick to answer any questions. Easy to get to and easy to get into when we arrived. Thanks for a wonderful getaway!"
Old Orchard Beach Getaway| 2BD Cottage
Escape to Pine Point: Beach Home with Fire Pit
10.0 out of 10, Exceptional, (11)
"We felt right at home as we walked in and then settled in. All the basics were covered and the owner quite friendly and responsive to needs. Only a short block away from the beach, which was beautiful to walk every day we were there even in the cold & wind of winter! If we were to be in the area for a short stay, we would rent this location again. Only thing I’d ask to change is an updated stove with a quieter clock. Totally enjoyed my time there!"
Escape to Pine Point: Beach Home with Fire Pit
beautiful rooms at Belkis Beach Motel
6.8 out of 10, (16)
"Overall okay experience. Spent more time away from motel."
beautiful rooms at Belkis Beach Motel
Luxurious Penthouse with Modern Design in Downtown
Luxurious Penthouse with Modern Design in Downtown
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is NZ$768
includes taxes & fees
3 Jun - 4 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
Rent a room in the gorgeous Holt House
7.8 out of 10, Good, (12)
"This was such a cool house to stay in. The host was very responsive and the check in/out process couldn't have been easier."
Rent a room in the gorgeous Holt House
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (117)
"We had a wonderful stay. The property was beautiful and the hosts were very accommodating. They always made sure we had everything we needed. We could not have asked for a more comfortable stay in such a beautiful neighborhood. If we travel that way in the future, we will definitely try to stay again. Thank you."
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
A yurt in the trees. Close to Portland but close to nature. Treeyurt Maine
A yurt in the trees. Close to Portland but close to nature. Treeyurt Maine
Modern & Sunny House Steps from the Promenade. Private Parking!
10.0 out of 10, Exceptional, (10)
"We were so happy with this property, it was the perfect space for three busy moms to get away and relax together. So clean and well thought out, appreciated all the little touches. Easily walkable to everywhere we wanted to go in Portland. We will always remember getting to see the northern lights from the balcony! Will definitely come back here again, thanks for everything."
The price is NZ$829
includes taxes & fees
16 Jun - 17 Jun
Modern & Sunny House Steps from the Promenade. Private Parking!
Oceanside escape 🌊 perfect family getaway!
10.0 out of 10, Exceptional, (5)
"Very cute house to rent. Bed options were plentiful. Everything you need. Easy to get to town or local shopping. Nice biking around from here. Local bus route too. Host was a great communicator. Highly recommend!!"
Oceanside escape 🌊 perfect family getaway!
Munjoy Hill- Immaculately restored antique 1874 New Englander with private patio
10.0 out of 10, Exceptional, (8)
"We loved our stay and great house for my family to stay in. Christine was very responsive to my questions/emails. I would highly recommend this house!"
Munjoy Hill- Immaculately restored antique 1874 New Englander with private patio
Renovated 4 BD | Sleeps 9 | Amazing Backyard Area
10.0 out of 10, Exceptional, (4)
"House is beautiful!! Love the decor! Very spacious,clean and fit all of our needs for 6 adults and 2 children! Kids loved the toys that were there!!"
Renovated 4 BD | Sleeps 9 | Amazing Backyard Area
New Listing! Private 3 Bedroom Oceanfront Home, Peaks Island, Maine
10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at House at Table Rock. The sun-filled living room and deck with spectacular ocean views was the perfect way to wake up with our morning coffee. Host Jen’s beautiful home is very comfortable with fully equipped kitchen essentials and everything we needed for our island getaway. From the front deck, we watched lobstermen at work, sailboats, and the ferries carrying people from island to Island. This island home is a treasure and we can’t wait to come back next year!"
New Listing! Private 3 Bedroom Oceanfront Home, Peaks Island, Maine
Don't see what you're looking for?
See all available properties in Chebeague Island
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.

Other property types in Chebeague Island

2 duplex
3.0 star property
The price is NZ$613
includes taxes & fees
2 Jun - 3 Jun
2 duplex
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (75)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
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.

Chebeague Island Holiday Homes information

Number of reviews
270
Accommodation
434 Holiday Homes
Lowest Price
NZ$561
Highest Price
NZ$768

Recent Reviews in Chebeague Island
Expedia verified reviews