Chebeague Island Holiday Rentals

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Our top choices for Chebeague Island holiday rentals

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is NZ$410
includes taxes & fees
24 Feb - 25 Feb
Fantastic Waterfront Views

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is NZ$336
includes taxes & fees
24 Feb - 25 Feb
2 bedroom w/ expansive water views

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is NZ$451
includes taxes & fees
24 Feb - 25 Feb
1 Mi to Maine Street! Mcm-style Home in Brunswick

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8 reviews)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is NZ$370
includes taxes & fees
24 Feb - 25 Feb
Modern style in historic building in downtown Bath

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (146 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is NZ$201
includes taxes & fees
24 Feb - 25 Feb
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is NZ$554
includes taxes & fees
24 Feb - 25 Feb
Full sized home

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
The price is NZ$182
includes taxes & fees
22 Mar - 23 Mar
HomeAwhile

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7 reviews)
"We ahd a great stay in Maine over the 4th visiting family, eating good food and walking around in great weather. Great stay in Brunswick, easy in and easy out and all sorts of things Maine accessible. Would recommend for anyone looking for a hassle-free weekend in coastal Maine. "
United States
Tjorvi P.
The price is NZ$418
includes taxes & fees
1 Mar - 2 Mar
Brunswick Downtown Sugar Cube next to Bowdoin

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (28 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is NZ$365
includes taxes & fees
24 Feb - 25 Feb
Pine Point Beach private, quaint, charming studio.

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is NZ$558
includes taxes & fees
1 Mar - 2 Mar
Large, luxurious geodesic dome - 04

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is NZ$494
includes taxes & fees
24 Feb - 25 Feb
Modern, Luxurious, Cabin in the Woods - 17

Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is NZ$916
includes taxes & fees
24 Feb - 25 Feb
Sweet comfy cottage on Small Point Road

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (125 reviews)
"Great location for an our trip; laundry in basement "
United States
maria h.
The price is NZ$430
includes taxes & fees
24 Feb - 25 Feb
City Amenities, Casco Bay Sunrises and Natural Beauty

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is NZ$305
includes taxes & fees
24 Feb - 25 Feb
Sunny Spot with Private Parking.

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$600
includes taxes & fees
26 Feb - 27 Feb
Modern & Sunny House Steps from the Promenade. Private Parking!

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is NZ$845
includes taxes & fees
24 Feb - 25 Feb
Modern Getaway by the Sea

Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End
Munjoy Hill
9.8 out of 10, Exceptional, (52 reviews)
"Great location and cozy."
United States
Heather G.
The price is NZ$560
includes taxes & fees
24 Feb - 25 Feb
Cozy, Elegant and Bright 2 bed in the East End

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is NZ$1,063
includes taxes & fees
25 Feb - 26 Feb
Award Winning Luxury Carriage House a short stroll from town!

Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds
Brunswick
10.0 out of 10, Exceptional, (19 reviews)
"Great place, super convenient to downtown."
United States
Heather C.
The price is NZ$616
includes taxes & fees
9 Mar - 10 Mar
Beautiful Delightful 3BR Downtown Brunswick All King Beds

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is NZ$352
includes taxes & fees
3 Mar - 4 Mar
Peaceful & minutes from the Old Port with private parking
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 favorite 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 depends 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 NZ$182 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 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?

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough: This holiday home rental outside of Chebeague Island is on the beach, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.