Chebeague Island Vacation Rentals

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Vacation Rentals in Chebeague Island

Comfort Duplex, 3 Bedrooms | Private kitchen
2 duplex
3.0 star property
The price is CA $344
CA $512 total
includes taxes & fees
May 26 - May 27
2 duplex
On the beach
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
Exterior
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
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Beach nearby
Little Miss Cottages
2.5 star property
8.2 out of 10, Very good, (68)
"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
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (16)
"Excellent apartment in Old Port area of Portland. Bright, clean, updated, comfortable bed and furniture, lots of amenities. Would definitely stay there again!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Beach
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, (25)
"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
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
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
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.4 out of 10, Exceptional, (17)
"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 CA $246
CA $435 total
includes taxes & fees
Jun 12 - Jun 13
Large 2BD cottage 10 min to Pier & Beach Pets ok
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
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 CA $192
CA $377 total
includes taxes & fees
Jun 4 - Jun 5
2 min walk to the beach. Pet friendly condo
Property grounds
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, (32)
"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
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (88)
"We were in Portland for my daughter’s graduation. Had a very nice weekend trying different restaurants and enjoying lobster rolls."
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Fridge, microwave, oven, stovetop
Full sized home
9.4 out of 10, Exceptional, (3)
"It was a nice little house"
The price is CA $342
CA $469 total
includes taxes & fees
Jun 7 - Jun 8
Full sized home
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."
The price is CA $277
CA $651 total
includes taxes & fees
Jun 2 - Jun 3
Elegant condo - walk to Portland's best restaurants & Old Port
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
3 bedrooms, desk, iron/ironing board, travel crib
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 CA $378
CA $898 total
includes taxes & fees
May 30 - May 31
Beach House ∆ Prime Location ∆ Steps to the Ocean
2 bedrooms, cribs/infant beds, internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.0 out of 10, Good, (6)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Beach nearby
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, (6)
"It was great. Good location and very clean!"
The price is CA $219
CA $441 total
includes taxes & fees
Jun 5 - Jun 6
NEW TO THE MARKET - 1 block from the beach!
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!
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

Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1055)
"Always a lovely stay "
The price is CA $240
CA $273 total
includes taxes & fees
Jun 9 - Jun 10
The Westin Portland Harborview
Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1196)
"The hotel was very comfortable and the staff was friendly and helpful."
The price is CA $314
CA $395 total
includes taxes & fees
May 27 - May 28
Portland Harbor Hotel
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, (1504)
"All good"
The price is CA $122
CA $133 total
includes taxes & fees
Jun 9 - Jun 10
Casco Bay Hotel, Ascend Hotel Collection
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.

Everything you need to know about Chebeague Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chebeague Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chebeague Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chebeague Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chebeague Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chebeague Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chebeague Island vacation rentals we have selected for you start as low as CA $192 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chebeague Island rentals

At Expedia, we put the best Chebeague Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chebeague Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chebeague Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chebeague Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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

The Westin Portland Harborview

The Westin Portland Harborview

5/5 Excellent
"Always a lovely stay "
A verified traveller stayed at The Westin Portland Harborview
Posted 4 hours ago
The Westin Portland Harborview