A wooden pier leading to a marina with boats docked.

Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chebeague Island vacation rentals

A wooden house with a deck and a stone pathway leading to a grassy area.

1. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
$207 nightly
The price is $218
Oct 20 - Oct 21
Total with taxes and fees
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A wooden deck with outdoor seating and string lights.

2. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$339 nightly
The price is $369
Oct 5 - Oct 6
Total with taxes and fees
Full sized home
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

3. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (14 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.
$109 nightly
The price is $111
Oct 5 - Oct 6
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

4. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
$212 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
A cabin with two chairs facing a fire pit, surrounded by trees.

5. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
$322 nightly
The price is $351
Oct 6 - Oct 7
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
A street lined with buildings, one with a red door and a sign that reads "MINATO".

6. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
$262 nightly
The price is $286
Oct 20 - Oct 21
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A dining table with chairs, a potted plant, and decorative items.

7. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (8 reviews)
"Excellent in every way."
United States
Robert B.
$305 nightly
The price is $333
Oct 27 - Oct 28
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A living room with a sofa, armchairs, a coffee table, and a potted plant.

8. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$198 nightly
The price is $215
Oct 7 - Oct 8
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A black console table with a mirror above it, a lamp, and a potted plant beside it.

9. 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, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$307 nightly
The price is $335
Nov 1 - Nov 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

10. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
$203 nightly
The price is $215
Oct 4 - Oct 5
Total with taxes and fees
Mid Coast Getaway w/ water views
A covered porch with a view of a lake and trees.

11. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
$437 nightly
The price is $442
Oct 13 - Oct 14
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

12. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (34 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
$296 nightly
The price is $323
Oct 5 - Oct 6
Total with taxes and fees
Sunny Spot with Private Parking.
A lakeside property with a deck, picnic table, and barbecue grill.

13. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$334 nightly
The price is $364
Oct 3 - Oct 4
Total with taxes and fees
Camp Forever cottage
A beach with a wooden chair and a small building in the background.

14. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$469 nightly
The price is $512
Oct 26 - Oct 27
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A geodesic dome structure in a forest setting with a visible interior space.

15. Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
$651 nightly
The price is $710
Oct 25 - Oct 26
Total with taxes and fees
Modern dome w/ full bath + spa access - 04
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

16. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (20 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
$149 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Studio Apartment near downtown Walkable!
A spacious living room with large windows, a sofa, a chair, and a small table.

17. 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
$249 nightly
The price is $271
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
A two-story house with a covered porch, a garage, and a front yard with potted plants.

18. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$149 nightly
The price is $162
Oct 6 - Oct 7
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

19. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
$256 nightly
The price is $259
Oct 5 - Oct 6
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A modern house with a wooden exterior, a small garden, and a visible window.

20. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$429 nightly
The price is $467
Oct 4 - Oct 5
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"Great location. It had everything we needed."
christine 1-night trip
Posted 9 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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 $151 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.

Explore a world of travel with Expedia

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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental near Chebeague Island is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 games.

How many vacation rentals are there in Chebeague Island?

Expedia has 4 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 Portland Observatory, or get out into nature at a spot like Little John Island Preserve. Wolfe's Neck Woods State Park and Bailey Island Bridge 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.