A wooden pier leading to a marina with boats docked.

Chebeague Island Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chebeague Island vacation rentals

A cabin with two chairs facing a fire pit, surrounded by trees.

1. 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.
$236 nightly
The price is $257
Sep 15 - Sep 16
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
A wooden deck with outdoor seating and string lights.

2. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$339 nightly
The price is $369
Sep 22 - Sep 23
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. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.4 out of 10, Very Good, (12 reviews)
"Place was fine, good amount of space, host was very nice"
United States
Jillian F.
$146 nightly
The price is $147
Sep 15 - Sep 16
Total with taxes and fees
Private Entrance Residential Portland
A spacious living room with large windows, a sofa, a chair, and a small table.

4. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
$253 nightly
The price is $276
Sep 23 - Sep 24
Total with taxes and fees
1 Mi to Maine Street! MCM-Style Home in Brunswick
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

5. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (9 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
$234 nightly
The price is $249
Sep 20 - Sep 21
Total with taxes and fees
Mid Coast Getaway w/ water views
A narrow hallway with a window on the right, leading to a room with a visible door.

6. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
$214 nightly
The price is $233
Sep 22 - Sep 23
Total with taxes and fees
Modern style in historic building in downtown Bath
A lakeside property with a deck, picnic table, and barbecue grill.

7. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (67 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$335 nightly
The price is $365
Sep 16 - Sep 17
Total with taxes and fees
Camp Forever cottage
A dining table with chairs, a potted plant, and decorative items.

8. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Excellent in every way."
United States
Robert B.
$289 nightly
The price is $314
Sep 16 - Sep 17
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A treehouse with a wooden staircase and a small building with a colorful mural.

9. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.2 out of 10, Very Good, (29 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
$163 nightly
The price is $177
Sep 15 - Sep 16
Total with taxes and fees
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

10. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (18 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
$159 nightly
The price is $161
Sep 17 - Sep 18
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.

11. 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
Sep 23 - Sep 24
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.

12. 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, (170 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$152 nightly
The price is $166
Sep 22 - Sep 23
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A harbor with boats docked, a pier, and buildings in the background.

13. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay at Mat's place! Convenient location, very cute apartment with a lovely view of the water. Well equipped for a couple's weekend away. We appreciated the sharp knives for cooking and the comfy couch!"
United States
Charlotte B.
$358 nightly
The price is $390
Sep 15 - Sep 16
Total with taxes and fees
Casco Bay Vista
A wooden staircase with a wooden railing, surrounded by green foliage.

14. Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!

Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!
Bath
8.0 out of 10, Very Good, (19 reviews)
"Cute but aging small space, Near attractions"
United States
michael
$158 nightly
The price is $172
Sep 15 - Sep 16
Total with taxes and fees
Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

15. 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
Sep 28 - Sep 29
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A wooden bench on a rocky shore overlooking a calm body of water.

16. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
$376 nightly
The price is $409
Sep 22 - Sep 23
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

17. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 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
Sep 22 - Sep 23
Total with taxes and fees
Sunny Spot with Private Parking.
A building with a sign for "The Send Brewing Co." and a logo featuring a stylized tree.

18. 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.
$309 nightly
The price is $337
Sep 15 - Sep 16
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

19. 2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.

2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (25 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
$215 nightly
The price is $234
Sep 15 - Sep 16
Total with taxes and fees
2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.
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
Sep 20 - Sep 21
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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

8/10 Good
"Bedding was clean, soft and warm. Room had a working tv, coffee maker and microwave. Complimentary breakfast was warm and delicious. Parking area was clean. Air conditioner worked but was loud. Bathroom door squeaked and room carpet along with stairway carpet really needed replacement or a really good shampoo. Room rate was good for my stay."
Elizabeth 2-night trip
Posted 1 hour ago
Quality Inn & Suites South Portland

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 $161 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 Maine Narrow Gauge Railroad, 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 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.