Chebeague Island Holiday Rentals

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Holiday Rentals in Chebeague Island

Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (15)
"This was a great spot for a weekend away! The unit is well equipped with higher end finishes and furnishings which makes the u it well worth visiting. The roof deck was a lovely addition as well! We left on Sunday so was happy to be able to move the car close to the unit Saturday evening to make packing a breeze."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is HK$1,258
per night
16 May - 17 May
Glorious getaway on Portland's Eastern Promenade.
View from property
Popham Beach Direct Oceanfront Cottage Steps to the sand
10.0 out of 10, Exceptional, (44)
"We had a great stay. Check in and communication was easy. Due to storm damage, our original booked cottage was not available and Deb offered us a different (much larger) home without added cost. We greatly appreciated it so we didn't have to cancel our vacation. The home was very clean and had everything we needed and then some. The area is beautiful and the beach was very clean. You cannot beat the views from the home. We look forward to staying here again!"
Popham Beach Direct Oceanfront Cottage Steps to the sand
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3 bedrooms, desk, iron/ironing board, travel cot
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (35)
"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."
The price is HK$1,758
per night
19 May - 20 May
Beach House ∆ Prime Location ∆ Steps to the Ocean
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (51)
"Comfortable, clean, very well decorated apartment in a pleasant, walkable neighborhood. I highly recommend this property."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (174)
"Even with a snow/ice storm, the beach doesn’t disappoint! Beautiful sunrises, sunsets, and waves crashing. The condo was warm and cozy and I was very happy to be able to watch the Bruins on tv. Already planned my next visit!"
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Exterior
Quaint one-bedroom suite
9.8 out of 10, Exceptional, (37)
"Loved it!! Would definitely rent again"
The price is HK$781
per night
22 May - 23 May
Quaint one-bedroom suite
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (88)
"We had a great time and this rental was very clean. The host was wonderful and easy to communicate with. My only tiny complaint is that the bedroom radiator was really loud (as they tend to be) and I am a light sleeper, so they kept me up. Not any fault of the rental, just is what it is. 15 minute walk to everything. Lovely, overall."
The price is HK$1,758
per night
23 May - 24 May
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (74)
"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
Property grounds
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
9.6 out of 10, Exceptional, (10)
"This place is just as nice as it looks in the pictures! My friends and I had a blast! What we appreciated the most was how communicative Jason was with us, and how welcome he made us feel! 10/10 recommend. Awesome place! :)"
The price is HK$1,547
per night
20 May - 21 May
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
Private kitchen
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."
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (21)
"Stayed for a weekend for bachelorette party! Very clean, close to downtown and loved the hot tub."
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Property grounds
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"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
Aerial view
Everybody's favorite Maine beach location
9.2 out of 10, Wonderful, (12)
"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
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (15)
"The house was cozy and well equipped. We had a wonderful time."
The price is HK$1,172
per night
20 May - 21 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Fridge, microwave, oven, coffee/tea maker
4 min walk to the beach. Large 1BD Pets Ok
9.2 out of 10, Wonderful, (7)
"Our manager was available and very accommodating to our needs. I would recommend this rental to anyone."
The price is HK$742
per night
20 May - 21 May
4 min walk to the beach. Large 1BD Pets Ok
Beach/ocean view
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (112)
"Very clean and comfortable! We loved our time there!"
The price is HK$2,733
per night
27 May - 28 May
Oceanfront Condo! Spectacular Views From Private Large Balcony
Beach nearby
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, (22)
"Great place to stay"
The price is HK$664
per night
16 May - 17 May
2 min walk to the beach. Pet friendly condo
Beach
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, (110)
"Good location, owner was very responsive to our needs."
East Grand Ave Fabulous Cottage
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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

Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (641)
"Wonderful place to stay. Spotlessly clean, great decor, exceptionally nice staff. Very good location. "
The price is HK$1,909
per night
20 May - 21 May
Canopy by Hilton Portland Waterfront
Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1187)
"Rooms are nice, beds a little too hard, employees not very friendly. I did like you can get coffee in the morning in the lobby. Breakfast not so good. "
The price is HK$1,469
per night
19 May - 20 May
Portland Harbor Hotel
Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1054)
"The Westin is very conveniently located in downtown Portland. Great harbor view and wonderful staff."
The price is HK$1,367
per night
2 Jun - 3 Jun
The Westin Portland Harborview
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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  • Enter your travel dates to view the best deals on holiday rentals in Chebeague Island while they last

Look no further and take a look at our great range of rental properties in Chebeague Island!

Frequently asked questions

Are there holiday rentals in Chebeague Island?

Yes, there are holiday rentals close to the most popular sights in Chebeague Island, or you can select a more secluded option if you're looking for a relaxing stay. Chebeague Island is known for its shopping and restaurants.

What are some of the best holiday rentals that Chebeague Island has to offer?

Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦ : This holiday home rental outside of Chebeague Island is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Chebeague Island?

Expedia has 5 holiday 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 wider area.

What are holiday rentals like in Chebeague Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chebeague Island. Holiday rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.

Recent reviews of Chebeague Island properties
Expedia verified reviews

Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

5/5 Excellent
"They offer coffee but Maybe some water to drink by the lobby. "
A verified traveller stayed at Casco Bay Hotel, Ascend Hotel Collection
Posted 2 days ago
Casco Bay Hotel, Ascend Hotel Collection