Lodging Image

Chebeague Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
The price is ￥49,071
￥71,738 total
includes taxes & fees
Oct 10 - Oct 11
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.
The price is ￥31,849
￥54,431 total
includes taxes & fees
Oct 5 - Oct 6
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, (13 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.
The price is ￥13,212
￥16,641 total
includes taxes & fees
Sep 28 - Sep 29
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, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is ￥23,277
￥39,087 total
includes taxes & fees
Oct 20 - Oct 21
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.
The price is ￥40,484
￥60,586 total
includes taxes & fees
Oct 6 - Oct 7
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, (148 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is ￥26,337
￥41,565 total
includes taxes & fees
Sep 28 - Sep 29
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, (7 reviews)
"Excellent in every way."
United States
Robert B.
The price is ￥25,951
￥51,945 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is ￥13,668
￥27,756 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is ￥38,848
￥58,802 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is ￥14,863
￥31,426 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is ￥25,544
￥61,114 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is ￥30,984
￥48,345 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is ￥33,029
￥54,174 total
includes taxes & fees
Oct 3 - Oct 4
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.
The price is ￥36,860
￥75,321 total
includes taxes & fees
Oct 26 - Oct 27
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.
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, (19 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
The price is ￥14,037
￥25,330 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is ￥16,043
￥42,653 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is ￥20,289
￥25,544 total
includes taxes & fees
Sep 28 - Sep 29
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.
The price is ￥19,660
￥38,919 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is ￥21,964
￥69,346 total
includes taxes & fees
Oct 4 - Oct 5
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Comfortable beds, convenient location, free coffee and water available. Very clean"
Teri 3-night trip
Posted 2 hours ago
Portland Regency Hotel & Spa

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?

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 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.