Chebeague Island Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Chebeague Island holiday rentals

Desk, laptop workspace, free WiFi

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.6 out of 10, Exceptional, (8 reviews)
"Staff fabulous, very clean"
United States
Verronika
The price is HK$744
HK$811 total
includes taxes & fees
25 Mar - 26 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, (147 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is HK$705
HK$939 total
includes taxes & fees
29 Mar - 30 Mar
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is HK$1,449
HK$2,433 total
includes taxes & fees
29 Mar - 30 Mar
Modern, Luxurious Cabin in the Woods - 03
Property grounds

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is HK$1,650
HK$2,998 total
includes taxes & fees
25 Mar - 26 Mar
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Fridge, microwave, oven, stovetop

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 HK$3,329
HK$5,089 total
includes taxes & fees
25 Mar - 26 Mar
Award Winning Luxury Carriage House a short stroll from town!
Interior

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is HK$1,018
HK$2,852 total
includes taxes & fees
25 Mar - 26 Mar
Vacation Creation Downtown Brunswick 2King Beds
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (70 reviews)
"Had a really nice stay. "
United States
John F.
The price is HK$5,464
HK$8,269 total
includes taxes & fees
25 Mar - 26 Mar
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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$1,598
HK$2,613 total
includes taxes & fees
29 Mar - 30 Mar
Large, luxurious geodesic dome - 04
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$1,480
HK$2,561 total
includes taxes & fees
31 Mar - 1 Apr
Camp Forever cottage
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is HK$2,311
HK$3,595 total
includes taxes & fees
31 Mar - 1 Apr
Centerview cottage
Interior

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 HK$2,350
HK$4,014 total
includes taxes & fees
26 Mar - 27 Mar
Modern Getaway by the Sea
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$822
HK$1,689 total
includes taxes & fees
30 Mar - 31 Mar
2 bedroom w/ expansive water views
Private kitchen

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (96 reviews)
"Clean and comfortable. The gym was great."
United States
Shannon
The price is HK$1,237
HK$1,936 total
includes taxes & fees
19 Apr - 20 Apr
The Weldon Hotel
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$1,586
HK$2,865 total
includes taxes & fees
25 Mar - 26 Mar
Full sized home
TV

Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
Brunswick
9.6 out of 10, Exceptional, (9 reviews)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
The price is HK$979
HK$2,664 total
includes taxes & fees
25 Mar - 26 Mar
Classic New England 1st Floor 3 BR Downtown Brunswick
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$881
HK$1,874 total
includes taxes & fees
25 Mar - 26 Mar
Pine Point Beach private, quaint, charming studio.
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, (127 reviews)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is HK$846
HK$2,024 total
includes taxes & fees
25 Mar - 26 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty
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$1,028
HK$2,050 total
includes taxes & fees
25 Mar - 26 Mar
Fantastic Waterfront 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$783
HK$1,733 total
includes taxes & fees
30 Mar - 31 Mar
Modern style in historic building in downtown Bath
Fridge, microwave, oven, stovetop

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"What a wonderful weekend in Portland Maine. The property was exceptional and in a great area. We felt comfortable and safe for our stay. We had a great time!"
United States
Kristyn E.
The price is HK$2,177
HK$3,910 total
includes taxes & fees
25 Mar - 26 Mar
Harborview - Curated East End Escape w/ 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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The staff was particularly good and friendly."
Ronald 1-night trip
Posted 5 hours ago
Holiday Inn Portland-By the Bay by IHG

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?

Beach House ∆ Prime Location ∆ Steps to the Ocean: This holiday home rental outside of Chebeague Island is located on the waterfront, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 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 Wolfe's Neck Farm. 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.