Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chebeague Island vacation rentals

Dining
Escape to Positive Outlook

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is ￥13,116
￥29,581 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Escape to Positive Outlook
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

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (145)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is ￥14,035
￥18,698 total
includes taxes & fees
Dec 30 - Dec 31
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
2 bedrooms, desk, iron/ironing board, free WiFi
Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!

Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!

Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!
Bath
8.6 out of 10, Excellent, (10)
"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. "
United States
A M.
The price is ￥21,782
￥27,147 total
includes taxes & fees
Dec 28 - Dec 29
Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!
Interior
Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is ￥14,814
￥41,134 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Brunswick Downtown Sugar Cube next to Bowdoin
Microwave, oven, stovetop
Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is ￥15,594
￥34,505 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Modern style in historic building in downtown Bath
Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
2.0 star property
Blue Point
10.0 out of 10, Exceptional, (24)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is ￥12,475
￥31,105 total
includes taxes & fees
Dec 28 - Dec 29
Pine Point Beach private, quaint, charming studio.
Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"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 ￥15,126
￥31,445 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sunny Spot with Private Parking.
Terrace/patio
Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3)
"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 ￥33,102
￥54,632 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Modern, Luxurious, Cabin in the Woods - 17
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
The price is ￥13,567
￥27,536 total
includes taxes & fees
Dec 28 - Dec 29
Adorable Portland getaway on the Eastern Promenade
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is ￥24,561
￥47,975 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Fantastic Waterfront Views
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is ￥10,978
￥24,715 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful 1st Floor Apartment & Amazing Shower
Outdoor dining
Peaceful & minutes from the Old Port with private parking

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)
"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 ￥15,282
￥33,145 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Peaceful & minutes from the Old Port with private parking
Exterior
Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
The price is ￥16,997
￥30,425 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Cheerful 1 bedroom cottage only 50ft from beach
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very Good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is ￥15,594
￥33,825 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt
West Bayside
8.6 out of 10, Excellent, (16)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is ￥13,099
￥24,295 total
includes taxes & fees
Jan 1 - Jan 2, 2026
In-town no frills 2 bedroom apt
Smart TV, books
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.8 out of 10, Exceptional, (28)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
The price is ￥21,052
￥54,222 total
includes taxes & fees
Dec 28 - Dec 29
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Beach nearby
Escape to the Beach! Cozy Condo in downtown OOB.

Escape to the Beach! Cozy Condo in downtown OOB.

Escape to the Beach! Cozy Condo in downtown OOB.
Old Orchard Beach
9.6 out of 10, Exceptional, (26)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
The price is ￥14,035
￥31,956 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Escape to the Beach! Cozy Condo in downtown OOB.
1 bedroom, desk, free WiFi, bed sheets
Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake
2.0 star property
Windham
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is ￥16,140
￥20,993 total
includes taxes & fees
Dec 30 - Dec 31
Spacious Studio Near Sebago Lake
Outdoor dining
Camp Forever cottage

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Perfect location on the water for a weekend getaway"
United States
Lydia G.
The price is ￥29,473
￥52,522 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Camp Forever cottage
Beach nearby, sun loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean
Old Orchard Beach
10.0 out of 10, Exceptional, (55)
"Excellent location for an after Labor Day vacation. Easy access to the beach. Quiet street. Very nice accommodations with plenty of room. "
United States
Charles C.
The price is ￥22,104
￥76,106 total
includes taxes & fees
Dec 30 - Dec 31
Beach House ∆ Prime Location ∆ Steps to the Ocean
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

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"Staff was great. Room was amazing. My partner was in love with the tub. "
Riley 1-night trip
Posted 11 hours ago
Canopy by Hilton Portland Waterfront

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 vacation rentals in Chebeague Island?

Yes, we have vacation rentals near popular attractions in Chebeague Island, or you can select a secluded option if you're looking for relaxation. Chebeague Island is known for its shopping and restaurants.

What's the top vacation rental in Chebeague Island?

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families! : This vacation home rental near Chebeague Island is located in the city center and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Chebeague Island?

Expedia has 3 vacation 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 Maine Narrow Gauge Railroad Company and Museum, or get out into nature at a spot like Casco Bay. Wolfe's Neck Woods State Park and Sand Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Chebeague Island?

Vacation rentals are private properties you can book for several days or more in Chebeague Island. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a small group gathering.