Chebeague Island Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Chebeague Island holiday rentals

Interior

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 HK$571
HK$2,109 total
includes taxes & fees
24 Mar - 25 Mar
1 Mi to Maine Street! Mcm-style Home in Brunswick
TV

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 HK$739
HK$1,562 total
includes taxes & fees
9 Mar - 10 Mar
2 bedroom w/ expansive water views
Interior

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 HK$782
HK$1,730 total
includes taxes & fees
8 Mar - 9 Mar
Modern style in historic building in downtown Bath
Desk, laptop workspace, free WiFi

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
The price is HK$669
HK$729 total
includes taxes & fees
11 Mar - 12 Mar
HomeAwhile
Exterior

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 HK$704
HK$938 total
includes taxes & fees
9 Mar - 10 Mar
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
3 bedrooms, WiFi

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is HK$985
HK$2,014 total
includes taxes & fees
13 Mar - 14 Mar
Fantastic Waterfront Views
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is HK$1,696
HK$3,712 total
includes taxes & fees
13 Mar - 14 Mar
Mere Point Sunrise Views at Eastern Shore!
Outdoor dining

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 HK$1,205
HK$2,106 total
includes taxes & fees
8 Mar - 9 Mar
Modern, Luxurious, Cabin in the Woods - 17
TV

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 HK$665
HK$1,926 total
includes taxes & fees
17 Mar - 18 Mar
Brunswick Downtown Sugar Cube next to Bowdoin
Smart TV

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 HK$880
HK$1,879 total
includes taxes & fees
12 Mar - 13 Mar
Pine Point Beach private, quaint, charming studio.
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is HK$493
HK$1,054 total
includes taxes & fees
8 Mar - 9 Mar
Private Entrance Residential Portland
Beach

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)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is HK$844
HK$2,003 total
includes taxes & fees
8 Mar - 9 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty
2 bedrooms, WiFi, bed sheets

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 HK$1,744
HK$2,830 total
includes taxes & fees
15 Mar - 16 Mar
Large, luxurious geodesic dome - 04
Outdoor dining

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 HK$767
HK$1,688 total
includes taxes & fees
10 Mar - 11 Mar
Peaceful & minutes from the Old Port with private parking
Interior

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15 reviews)
"The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. "
United States
Michael S.
The price is HK$618
HK$1,918 total
includes taxes & fees
11 Mar - 12 Mar
Little Lincoln beautiful home
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,643
HK$2,839 total
includes taxes & fees
2 Apr - 3 Apr
Camp Forever cottage
Interior

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 HK$758
HK$1,577 total
includes taxes & fees
12 Mar - 13 Mar
Sunny Spot with Private Parking.
Terrace/patio

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 HK$1,583
HK$2,859 total
includes taxes & fees
9 Mar - 10 Mar
Full sized home
3 bedrooms, premium bedding, iron/ironing board, travel cot

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is HK$1,040
HK$3,009 total
includes taxes & fees
8 Mar - 9 Mar
Cozy 3BR | Pet Friendly | Near Portland | Parking
Outdoor dining

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 HK$1,243
HK$2,531 total
includes taxes & fees
8 Mar - 9 Mar
Modern & Sunny House Steps from the Promenade. 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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Airport shuttle was great. Staff was appropriately friendly. Room was clean and inviting."
Susan 1-night trip
Posted 3 hours ago
Embassy Suites by Hilton Portland Maine

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:

  • View our selection of featured holiday rentals in Chebeague Island
  • Use the map to find apartments and other holiday homes in the Chebeague Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chebeague Island while they last

Look no further and take a look at our great range of rental properties 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?

Ocean Views! Walk to the Beach!: This holiday home rental outside of Chebeague Island is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.