Chebeague Island Vacation Rentals

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Our top choices for Chebeague Island vacation rentals

10.0 out of 10, Exceptional, (8)
"Clean comfortable and right downtown"
United States
stephen e.
$203 nightly
The price is $221
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern style in historic building in downtown Bath
10.0 out of 10, Exceptional, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
$110 nightly
The price is $120
Dec 22 - Dec 23
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Vacation Home in West Point

Escape to Positive Outlook
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.
$180 nightly
The price is $189
Jan 4 - Jan 5, 2026
Total with taxes and fees
Escape to Positive Outlook
8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
$244 nightly
The price is $266
Jan 1 - Jan 2, 2026
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin
2.0 star property
10.0 out of 10, Exceptional, (24)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
$183 nightly
The price is $199
Dec 22 - Dec 23
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
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.
$153 nightly
The price is $167
Jan 21 - Jan 22, 2026
Total with taxes and fees
Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.
9.8 out of 10, Exceptional, (7)
"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.
Mere Point Sunrise Views at Eastern Shore!

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
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
$165 nightly
The price is $180
Dec 22 - Dec 23
Total with taxes and fees
Sunny Spot with Private Parking.
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.
$272 nightly
The price is $296
Dec 22 - Dec 23
Total with taxes and fees
Modern, Luxurious, Cabin in the Woods - 17
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.
$181 nightly
The price is $198
Dec 22 - Dec 23
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$127 nightly
The price is $138
Dec 23 - Dec 24
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
$149 nightly
The price is $162
Dec 22 - Dec 23
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
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.
$195 nightly
The price is $213
Jan 5 - Jan 6, 2026
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
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.
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
2.0 star property
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
$124 nightly
The price is $135
Dec 30 - Dec 31
Total with taxes and fees
Spacious Studio Near Sebago Lake
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
$239 nightly
The price is $261
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy, Elegant and Bright 2 bed in the East End

Vacation Home in West Point

Fantastic Waterfront Views
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.
$294 nightly
The price is $311
Jan 11 - Jan 12, 2026
Total with taxes and fees
Fantastic Waterfront Views
9.6 out of 10, Exceptional, (18)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
$300 nightly
The price is $327
Dec 22 - Dec 23
Total with taxes and fees
Vacation Creation Downtown Brunswick 2King Beds
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
$198 nightly
The price is $215
Dec 22 - Dec 23
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
2.0 star property
$281 nightly
The price is $307
Dec 28 - Dec 29
Total with taxes and fees
Cozy 1-bedroom apartment in lovely Gorham
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 vacation rentals

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

Chebeague Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chebeague Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chebeague Island rentals

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

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 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.