Chebeague Island Vacation Rentals

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Vacation Rentals in Chebeague Island

2 duplex
Comfort Duplex, 3 Bedrooms | Private kitchen | Fridge, microwave, oven, dishwasher
2 duplex
3.0 star property
2 duplex
Gorgeous ocean-front home with stunning beach views
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, 75 reviews
"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
NEW TO THE MARKET - 1 block from the beach!
Beach nearby
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, 7 reviews
"It was great. Good location and very clean!"
The price is ￥38,718
￥67,355 total
includes taxes & fees
Jun 12 - Jun 13
NEW TO THE MARKET - 1 block from the beach!
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Full sized home
Fridge, microwave, oven, stovetop
Full sized home
9.6 out of 10, Exceptional, 4 reviews
"Great place to stay. Host was helpful and responsive."
The price is ￥38,718
￥53,175 total
includes taxes & fees
Jun 7 - Jun 8
Full sized home
Quaint one-bedroom suite
1 bedroom, WiFi
Quaint one-bedroom suite
9.8 out of 10, Exceptional, 38 reviews
"Quiet peaceful great accommodations and wonderful host"
The price is ￥15,591
￥22,092 total
includes taxes & fees
Jun 19 - Jun 20
Quaint one-bedroom suite
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
Beach
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, 25 reviews
"The unit has a really nice view of downtown and the pier. Cool view of the ferris wheel lit up at night. At first glance, the unit is nicely decorated. However, it needs to be refreshed - there are chunks missing out of the walls, things falling apart, ongoing water damage next to the tub. Maintenance from the building came by on the first morning of the stay to check on the kitchen sink because there was a massive leak happening to the unit below. Overall, it seemed as if no one has been...
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
Everybody's favorite Maine beach location
Aerial view
Everybody's favorite Maine beach location
9.2 out of 10, Wonderful, 12 reviews
"The property was updated and very clean. The pillows were not very good, but the bed was great! The location was not where we anticipated. It was very easy checking in and out."
Everybody's favorite Maine beach location
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.4 out of 10, Exceptional, 17 reviews
"The cottage was clean and accurately described. It was perfect for our needs and we are already looking forward to staying there again in the future."
The price is ￥27,877
￥49,292 total
includes taxes & fees
Jun 12 - Jun 13
Large 2BD cottage 10 min to Pier & Beach Pets ok
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen | Fridge, microwave, oven, stovetop
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 45 reviews
"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 ￥32,117
￥74,392 total
includes taxes & fees
Jun 17 - Jun 18
Elegant condo - walk to Portland's best restaurants & Old Port
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, 176 reviews
"Watching and listening to the ocean was all i needed."
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Exterior
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
9.8 out of 10, Exceptional, 12 reviews
"This is a great spot to stay no matter what time of the year!! Completely enjoyed my stay!!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Private kitchen | Fridge, microwave, oven, stovetop
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, 89 reviews
"Six of us stayed for our daughter's graduation. Nicely appointed property! We were able to walk to dinner, and it was a short drive to our other activities. Highly recommend!"
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Little Miss Cottages
Beach nearby
Little Miss Cottages
2.5 star property
8.2 out of 10, Very Good, 68 reviews
"Perfect place for a family to stay for a fair price if you want to stay a few nights and tour around the rest of Maine. Beach was wonderful! "
Little Miss Cottages
100 feet from the ocean 3 bedroom cottage 420 friendly
Property grounds
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, 13 reviews
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Smart TV, books
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.8 out of 10, Exceptional, 27 reviews
"We spent our 19th wedding anniversary here. It was the perfect romantic getaway. The views are stunning and the location is tranquil. Just a short drive to the general store for necessities, and Uber Eats delivers. We didn’t want to leave. Would 100% stay here again."
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
2 min walk to the beach. Pet friendly condo
Beach nearby
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, 24 reviews
"Overall a good stay for the price and convenient to everything. Kinda dated and could use some upgrades. "
The price is ￥14,713
￥33,762 total
includes taxes & fees
Jun 10 - Jun 11
2 min walk to the beach. Pet friendly condo
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Fridge, microwave, oven, stovetop
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
The price is ￥58,934
￥111,312 total
includes taxes & fees
Jun 9 - Jun 10
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, 19 reviews
"Dana, the owner, was more than accommodating. She went out of her way to accommodate our needs. The unit was outstanding in design, cleanliness, and location. We were close to restaurants, shopping, and the harbor. We loved it and hated to leave. This unit definitely enhanced our visit to Portland."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
4 min walk to the beach. A large 3DB Apt. Pets OK
Fridge, microwave, oven, stovetop
4 min walk to the beach. A large 3DB Apt. Pets OK
8.6 out of 10, Excellent, 7 reviews
"We found this place and booked after seeing it was pet friendly and close to the beach which was a must for our beach loving family and pups. Our stay was lovely- it’s a few blocks to the beach and into the main town area. The place was clean, had a good amount of space, was quiet, and a small deck area to sit outside. Communications with the host were easy and they checked in on us part way through to ensure our stay was going well."
The price is ￥23,231
￥48,280 total
includes taxes & fees
Jun 10 - Jun 11
4 min walk to the beach. A large 3DB Apt. Pets OK
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel crib
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, 35 reviews
"The cottage was very nice but the write-up was a little misleading. For example ocean views are very limited—mostly see rooftops, half bath was on ground floor, and stairs to main living area."
Beach House ∆ Prime Location ∆ Steps to the Ocean
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 types of properties in Chebeague Island you may be interested in

Casco Bay Hotel, Ascend Hotel Collection
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, 1,562 reviews
"The room was gigantic and nice. The lobby was very pretty. My only complaint is the outside is not very inviting but not much can be done about that. The room was really great and had pick up/ drop off to airport"
The price is ￥22,162
￥24,157 total
includes taxes & fees
Jun 12 - Jun 13
Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed | Premium bedding, desk, blackout drapes, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, 1,192 reviews
"Property had charm, spacious room and centrally located "
The price is ￥36,343
￥46,107 total
includes taxes & fees
Jun 10 - Jun 11
Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, 663 reviews
"Stayed a couple of days. Valet was actually excellent, quick, and efficient. The guys doing valet were auper on it and friendly. Check in was very easy. Roman and Alicia at the front desk were great, providing us with amazing service. I will say, the room was not the cleanest. Dog hair was all over, and there was a lot of dust on the very cute wooden walls. Baseboards in our room really needed help. So, yeah, like a 3 on cleanliness, because my allergies were off the wall! But the rooms are...
The price is ￥54,413
￥60,127 total
includes taxes & fees
Jun 9 - Jun 10
Canopy by Hilton Portland Waterfront
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.

Search for holiday rentals in Chebeague Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Chebeague Island using one of the methods below:

  • View our selection of featured holiday rentals in Chebeague Island
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Look no further and take a look at our great range of rental properties in Chebeague Island!

Frequently asked questions

Are there vacation rentals in Chebeague Island?

Yes, we have vacation rentals near popular attractions in Chebeague Island, or you can select a secluded option if you're looking for relaxation. Chebeague Island is known for its shopping and restaurants.

What's the top vacation rental in Chebeague Island?

Rent a room in the gorgeous Holt House: This vacation home near Chebeague Island has air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals are there in Chebeague Island?

Expedia has 5 vacation rentals for your stay in Chebeague Island.

What can I see and do in Chebeague Island?

Explore the area and family-friendly sights such as Maine Wildlife Park, or get out into nature at a spot like Wolfe's Neck Woods State Park. Bailey Island Bridge and Casco Bay are a couple of places you'll find in the larger area.

What are vacation rentals like in Chebeague Island?

Vacation rentals are private properties you can book for several days or more in Chebeague Island. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a small group gathering.

Recent reviews of Chebeague Island properties
Expedia verified reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

5/5 Excellent
"Historic building with character. Affordable. Comfortable. Convenient. Walkable to hospital. Short city drive to other sites & activities. No frills. Stairs only, somewhat steep for older guests. Private bathrooms accessed via hall. Street parking available when parking lot fills up. Would come here again."
A verified traveler stayed at Inn at St John Portland In-Town
Posted 1 day ago
Inn at St John Portland In-Town