Chebeague Island Holiday Rentals

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Holiday Rentals in Chebeague Island

Captain's Guest Room w/private bath & house entrance. Walk to everything.
8.0 out of 10, Very good, (19)
"Dmitri is accommodating and check-in easy. Property details are accurate "
The price is AU$237
includes taxes & fees
2 Nov - 3 Nov
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Modern style in historic building in downtown Bath
10.0 out of 10, Exceptional, (8)
"Property was nice little apartment with what I needed"
The price is AU$347
includes taxes & fees
17 Oct - 18 Oct
Modern style in historic building in downtown Bath
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, (140)
"Wonderful hosts, truly made guests feel welcomed and valued. "
The price is AU$187
includes taxes & fees
2 Nov - 3 Nov
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Camp Forever cottage
9.6 out of 10, Exceptional, (56)
"Most enjoyed vacation this year.Location was beautiful. "
The price is AU$422
includes taxes & fees
22 Oct - 23 Oct
Camp Forever cottage
Modern, luxurious cabin in the woods - 19
10.0 out of 10, Exceptional, (3)
"Great location to Freeport shopping. Very clean and responsive staff and management. Fun for families with children. We would have liked more room inbetween cabins, but otherwise would highly recommend."
The price is AU$376
includes taxes & fees
29 Oct - 30 Oct
Modern, luxurious cabin in the woods - 19
King Size Sun Rise Midcoast Lovely Stay
10.0 out of 10, Exceptional, (14)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
The price is AU$360
includes taxes & fees
3 Nov - 4 Nov
King Size Sun Rise Midcoast Lovely Stay
Little Lincoln beautiful home
9.2 out of 10, Wonderful, (12)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
The price is AU$415
includes taxes & fees
22 Oct - 23 Oct
Little Lincoln beautiful home
Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (23)
"Wonderful stay!"
The price is AU$311
includes taxes & fees
2 Nov - 3 Nov
Sunny Spot with Private Parking.
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
10.0 out of 10, Exceptional, (2)
"Wonderful property with great ocean views! The house was very nice, comfortable and quiet. Found the bed to be very comfortable. Would highly recommend to anyone that is interested in staying in this area."
The price is AU$871
includes taxes & fees
8 Nov - 9 Nov
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (123)
"So clean! Loved all the little notes, very helpful. Such a great location close to the water and would definitely recommend this place in the future."
The price is AU$322
includes taxes & fees
3 Nov - 4 Nov
Adorable Portland getaway on the Eastern Promenade
Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!
9.4 out of 10, Exceptional, (31)
"Loved the location, it was the perfect size fit myself and my daughter stayed a couple of days too! The kitchen is terrific with a lovely view of the marsh. Such a happy place to visit and stay!!"
The price is AU$546
includes taxes & fees
19 Oct - 20 Oct
Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
8.0 out of 10, Very good, (24)
"Property was just as expected. It was nice for us. Only complaint was the grill was broken and we didn’t realize it until after we went and purchased meats for the grill"
The price is AU$386
includes taxes & fees
22 Oct - 23 Oct
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Fantastic Waterfront Views
9.8 out of 10, Exceptional, (10)
"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. "
The price is AU$477
includes taxes & fees
9 Nov - 10 Nov
Fantastic Waterfront Views
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
9.8 out of 10, Exceptional, (27)
" Very spacious, clean and beautiful."
The price is AU$600
includes taxes & fees
9 Nov - 10 Nov
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (23)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
The price is AU$276
includes taxes & fees
10 Nov - 11 Nov
Beautiful 1st Floor Apartment & Amazing Shower
Centerview cottage
9.6 out of 10, Exceptional, (58)
"The title says it all. Property owners have their own separate house on site, along with a few other rental cottages. Properties share a common dock that is in excellent condition. Owners were super welcoming, friendly, and reachable if needed. "
The price is AU$638
includes taxes & fees
27 Oct - 28 Oct
Centerview cottage
Beautiful Delightful 3BR Downtown Brunswick All King Beds
10.0 out of 10, Exceptional, (18)
"House was great for our family of four "
The price is AU$521
includes taxes & fees
22 Oct - 23 Oct
Beautiful Delightful 3BR Downtown Brunswick All King Beds
The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (84)
"Loved this place and would definitely stay here next time we go back."
The price is AU$424
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
9.4 out of 10, Exceptional, (96)
"The house is good and reasonably appointed for a short stay. Beds quite comfortable and home is clean You can walk to downtown port area easily. Very peaceful residential street. Enjoyed our short visit. "
The price is AU$417
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
The price is AU$974
includes taxes & fees
20 Oct - 21 Oct
Waterfront Access with Kayaks, Private Deck and a Firepit
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.
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Top Chebeague Island Hotel Reviews

Find out more about Chebeague Island

Everything you need to know about Chebeague Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chebeague Island holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chebeague Island holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chebeague Island holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chebeague Island holiday rentals we have selected for you start as low as AU$217 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chebeague Island rentals

At Expedia, we put the best Chebeague Island holiday 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 holiday.

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 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?

Captain's Guest Room w/private bath & house entrance. Walk to everything.: This holiday home rental outside of Chebeague Island comes with WiFi so that you can feel at home during your trip. Kitchen amenities include an electric kettle to make your meal-planning easier.

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 Portland Observatory, 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.