Chebeague Island Holiday Rentals: Short-Term Accommodations for Rent

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Holiday Rentals in Chebeague Island

HK$2,719 total

includes taxes & fees

13 Jul - 14 Jul

HK$2,210 total

includes taxes & fees

13 Jul - 14 Jul

"Property had beautiful views of the surrounding area. Very spacious living areas, bedrooms and bathrooms. Could use a bit of a cleaning in some areas and better organization of outdoor furniture."

HK$3,959 total

includes taxes & fees

13 Jul - 14 Jul

"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "

HK$4,469 total

includes taxes & fees

15 Jul - 16 Jul

"This property exceeded my expectations with its charming exterior holding true to its original character while offering a modern exceptional interior filled with amenities. It is clear that the owners had a vision to provide the ultimate guest experience. They were also very responsive to my questions and invited me over for a glass of wine. I cannot wait to make a return trip and stay longer!"

HK$4,458 total

includes taxes & fees

14 Jul - 15 Jul

"Very nice cozy place to make home base for a week. Had everything I needed and owner was very responsive with all of my questions. Primary destination was Bath and very convenient to everything I needed. Thank you!"

HK$1,283 total

includes taxes & fees

13 Jul - 14 Jul

"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."

HK$1,283 total

includes taxes & fees

13 Jul - 14 Jul

"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "

HK$1,788 total

includes taxes & fees

13 Jul - 14 Jul

"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."

HK$2,824 total

includes taxes & fees

13 Jul - 14 Jul

HK$14,426 total

includes taxes & fees

11 Jul - 12 Jul

HK$12,638 total

includes taxes & fees

11 Jul - 12 Jul

"Nice place, I'd stay again!"

HK$3,885 total

includes taxes & fees

20 Jul - 21 Jul

"Had a great stay here, the property was clean and came as advertised"

HK$3,354 total

includes taxes & fees

15 Jul - 16 Jul

"Great property with a great view. No ac was a bummer Washing machine kept erroring out a few mins after starting Grill brush was broke upon arrival Grill was very dirty and starting grease fires, so we cleaned it May want to check leaking of kitchen sink or dishwasher. When washing clothes I noticed the ceiling is wet right under the kitchen sink area "

HK$4,034 total

includes taxes & fees

25 Jul - 26 Jul

"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "

HK$8,126 total

includes taxes & fees

21 Jul - 22 Jul

"Great location - close to downtown Freeport. Beautiful property with plenty of comfortable sleeping options"

HK$24,007 total

includes taxes & fees

4 Aug - 5 Aug

"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "

HK$6,851 total

includes taxes & fees

27 Jul - 28 Jul

"I spent summers on Long Island in Casco Bay always dreaming of staying at Peak’s Island to see what all the hype was about… Well, it exceeded my expectations at this location! The communication with the owner, to the comfort of the cottage and view was priceless. We are already planning for next summer 😃"

HK$9,883 total

includes taxes & fees

4 Aug - 5 Aug

"Cozy and clean place with a quick walk to the beach in beautiful neighborhood!"

HK$2,969 total

includes taxes & fees

7 Aug - 8 Aug

"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "

HK$1,814 total

includes taxes & fees

28 Jul - 29 Jul

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Find out more about Chebeague Island

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:

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Recent reviews of Chebeague Island properties

5/5 Excellent

"Convince to the airport"

A verified traveller stayed at Tru by Hilton Portland Airport Area

Posted 1 day ago

5/5 Excellent

"We got here a little early about 11:49am) and asked to use the restroom, then we would come back later. I did explain that we did have a room booked. The lady just said no, barhroom was being cleaned. I could see the bathroom and it was not being cleaned. I think she should have asked for my i.d. , and once confirmed reservation, we use restroom. This was disappointing. However, when we did check in, it was a different staff person and she was amazing. Polite, respectful, charming. I will say this: Iwent down for coffee at 3:15ish and bathroom was being cleaned. So, does this mean the receptionist just did not want to be bothered earlier when we asked to use restroom? We were staying here "

A verified traveller stayed at Comfort Inn Airport

Posted 2 days ago

5/5 Excellent

Fabulous hotel in an Excellent location

"An absolutely fabulous hotel, with friendly helpful staff from check-in to housekeeping. Our room was clean and spacious, the toiletries were good quality and there was plenty of thick towels. The bed was huge and incredibly comfortable. The location was perfect for all the tours we had booked, (trolley, boat cruise and several walking tours) and were all within a 10 minute walk from the hotel. Bars, restaurants and shops were all close by. This was our first time in Portland and we had a great time. I would 100% recommend this hotel for anyone visiting Portland."

A verified traveller stayed at Portland Regency Hotel & Spa

Posted 3 days ago

5/5 Excellent

"We loved everything about this hotel. We now know the place to stay next time we are in Portland longer then one night. The pool looked amazing, just didn't have time to enjoy after our touring around the town. Everything is right there in town near the hotel to enjoy yourself. "

A verified traveller stayed at Holiday Inn Portland-By the Bay by IHG

Posted 3 days ago

5/5 Excellent

Reliable good stay

"Always a reliable, convenient good stay in Portland. Small rooms and beds, limited plug connections, separate bathrooms, no elevators, are minuses. But price, service, upkeep, breakfast, lobby area, parking, and location are pluses."

A verified traveller stayed at Inn at St John Portland In-Town

Posted 3 days ago

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All accommodation types 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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This holiday home rental outside of Chebeague Island offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chebeague Island?

Expedia has 3 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 Land's End Gift Shop, or get out into nature at a spot like Casco Bay. Wolfe's Neck Woods State Park and Bailey Island Bridge 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.

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Chebeague Island Holiday Rentals

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Holiday Rentals in Chebeague Island

Escape to Positive Outlook

Mid Coast Getaway w/ water views

Phenomenal Home on Coast of Maine

Fantastic Waterfront Views

Award Winning Luxury Carriage House a short stroll from town!

1BR Guest Apartment. Great Value. Walk to everything.

1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!

Captain's House 2BR Apartment. Walk to Everything!

Camp Forever cottage

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Classic New England Waterfront

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Mere Point Sunrise Views at Eastern Shore!

Waterfront Spacious Luxury Home, 5 min to LL Bean!

Waterfront, Luxury, Spacious home in Freeport!

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Willard Beach–Private Apt Near Portland & Parks

Charming Studio apartment with WiFi, AC in welcoming Portland

Find out more about Chebeague Island

Recent reviews of Chebeague Island properties

Tru by Hilton Portland Airport Area

Comfort Inn Airport

Portland Regency Hotel & Spa

Holiday Inn Portland-By the Bay by IHG

Inn at St John Portland In-Town

Clarion Hotel Portland

La Quinta Inn & Suites by Wyndham Portland

Portland Harbor Hotel

Cambria Hotel Portland Downtown-Old Port

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Frequently asked questions