A wooden pier leading to a marina with boats docked.

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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chebeague Island vacation rentals

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 CA $239
CA $433 total
includes taxes & fees
Sep 27 - Sep 28
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

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 CA $286
CA $514 total
includes taxes & fees
Oct 5 - Oct 6
Full sized home

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 CA $119
CA $150 total
includes taxes & fees
Sep 28 - Sep 29
Portland 1-bedroom with enclosed porch & parking

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 CA $209
CA $364 total
includes taxes & fees
Oct 20 - Oct 21
Charming Studio apartment with WiFi, AC in welcoming Portland

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 CA $364
CA $576 total
includes taxes & fees
Oct 6 - Oct 7
Modern cabin w/ full bath & kitchenette - 03

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 CA $237
CA $385 total
includes taxes & fees
Sep 27 - Sep 28
Adorable Portland getaway on the Eastern Promenade

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 CA $233
CA $495 total
includes taxes & fees
Sep 29 - Sep 30
Willard Beach–Apartment Near Portland & Parks

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 CA $107
CA $233 total
includes taxes & fees
Sep 27 - Sep 28
Beautiful 1st Floor Apartment & Amazing Shower

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 CA $297
CA $493 total
includes taxes & fees
Sep 27 - Sep 28
Peaceful & minutes from the Old Port with private parking

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 CA $134
CA $287 total
includes taxes & fees
Sep 29 - Sep 30
Mid Coast Getaway w/ water views

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 CA $262
CA $630 total
includes taxes & fees
Oct 13 - Oct 14
Mere Point Sunrise Views at Eastern Shore!

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 CA $279
CA $458 total
includes taxes & fees
Sep 29 - Sep 30
Sunny Spot with Private Parking.

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 CA $297
CA $515 total
includes taxes & fees
Oct 3 - Oct 4
Camp Forever cottage

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 CA $331
CA $711 total
includes taxes & fees
Oct 26 - Oct 27
Arlie`s Digs! - One Block To Willard Beach!

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

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 CA $126
CA $228 total
includes taxes & fees
Oct 6 - Oct 7
Studio Apartment near downtown Walkable!

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 CA $144
CA $384 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! Mcm-style Home in Brunswick

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 CA $182
CA $230 total
includes taxes & fees
Sep 28 - Sep 29
Large suite/private bath/private entrance on quiet street near Thomas Bay

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 CA $177
CA $363 total
includes taxes & fees
Sep 28 - Sep 29
King Size Sun Rise Midcoast Lovely Stay

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 CA $197
CA $664 total
includes taxes & fees
Oct 15 - Oct 16
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chebeague Island Hotel Reviews

Find out more about Chebeague Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chebeague Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.