Chebeague Island Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chebeague Island

2 duplex
3.0 star property
The price is NZ$1,500
includes taxes & fees
4 July - 5 July
2 duplex
Full sized home
9.6 out of 10, Exceptional, 4 reviews
"Great place to stay. Host was helpful and responsive."
The price is NZ$555
includes taxes & fees
27 June - 28 June
Full sized home
Quaint one-bedroom suite
9.8 out of 10, Exceptional, 40 reviews
"Room was as pictured and described. Ms. Dot greeted us warmly and it was obvious the owners went out of their way to provide anything we might need...from toiletries, to coffee, to paper goods, to lots of TV viewing options. We were told we were welcome to use the deck as well as the laundry room. We were very comfortable! The neighborhood is beautiful, as is the front yard. Bath is a lovely little town with lots of restaurants and shops. Reny's was awesome!"
The price is NZ$326
includes taxes & fees
26 June - 27 June
Quaint one-bedroom suite
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, 8 reviews
"This property isn't large, but was absolutely perfect for a quick getaway for my husband and me. The owners were extremely responsive, and provide you with all of the kitchen/bathroom essentials that you need. The condo was very clean, in walking distance to shops/restaurants/the pier, and the beach is just a short walk across the street. We look forward to renting here again in the future!"
The price is NZ$707
includes taxes & fees
26 June - 27 June
NEW TO THE MARKET - 1 block from the beach!
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, 78 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
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.
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
2 min walk to the beach. Pet friendly condo
8.8 out of 10, Excellent, 26 reviews
"Overall a good stay for the price and convenient to everything. Kinda dated and could use some upgrades. "
The price is NZ$518
includes taxes & fees
27 June - 28 June
2 min walk to the beach. Pet friendly condo
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
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!!"
The price is NZ$1,192
includes taxes & fees
19 July - 20 July
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, 20 reviews
"This apartment is fantastic! Great location, perfectly appointed, and Dena was awesome with her communications. The roof deck is a great bonus."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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 NZ$866
includes taxes & fees
10 July - 11 July
4 min walk to the beach. A large 3DB Apt. Pets OK
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 47 reviews
"My two sisters and I loved everything about the place especially the kitchen and the temperature control via AC or heat. The only concern about the place is that it took 1-3 tries each time we had to unlock the front door by code. There was supposed to be music to help but couldn't really hear anything. May need some attention but have to admit we never alerted anyone at the time thinking it was related to our ineptitude! I tried to do this review on the Vacasa site but the page never came up...
The price is NZ$837
includes taxes & fees
8 July - 9 July
Elegant condo - walk to Portland's best restaurants & Old Port
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, 33 reviews
"I rated this property a 4 and not lower because of its location. It is front-facing to the ocean, and that is always a gem in my book. Sleeping to the sound of the waves is amazing. The property management (Vacasa) was flawless in their communication and the housekeeping staff did a great job cleaning what they were responsible for cleaning. BUT....... this unit is in dire need of some deep cleaning and at a minimum some TLC in painting and in fixing what doesn't work (i.e., windows, toilet...
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
The price is NZ$1,330
includes taxes & fees
24 June - 25 June
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Everybody's favorite Maine beach location
9.4 out of 10, Exceptional, 13 reviews
"The property was clean and spacious for four 25 year old men to comfortably stay for the weekend."
The price is NZ$1,366
includes taxes & fees
21 July - 22 July
Everybody's favorite Maine beach location
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
350 Yards to the beach. Pet friendly!
8.4 out of 10, Very good, 24 reviews
"Unit was clean but small enough for privacy"
The price is NZ$486
includes taxes & fees
24 June - 25 June
350 Yards to the beach. Pet friendly!
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, 114 reviews
"I loved the location!!! Great little place...restaurant downstairs was great."
The price is NZ$1,201
includes taxes & fees
9 July - 10 July
Oceanfront Condo! Spectacular Views From Private Large Balcony
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 NZ$599
includes taxes & fees
24 June - 25 June
Large 2BD cottage 10 min to Pier & Beach Pets ok
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
3.5 star property
8.6 out of 10, Excellent, 1,639 reviews
"This hotel newly renovated from what I understand is beautiful. Such a nice hidden gem. "
The price is NZ$207
includes taxes & fees
24 June - 25 June
Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, 1,043 reviews
"All the staff were so helpful and kind."
The price is NZ$440
includes taxes & fees
2 July - 3 July
The Westin Portland Harborview
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, 1,206 reviews
"All were good except that I hope it was better explained that the destination amenity fee of up to $35/day needs to be consumed per day itself and does not accumulate and be used any day/days of your stay. "
The price is NZ$629
includes taxes & fees
8 July - 9 July
Portland Harbor Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chebeague Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chebeague Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chebeague Island. Seeing all the best attractions is bound to make you fall in love with Chebeague Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chebeague Island short-term rentals, that won’t be hard to do.

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?

Rent a room in the gorgeous Holt House: This holiday home rental outside of 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 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