---
title: "Chebeague Island Vacation Rentals from CA $83: Short-Term Rentals for 2026 | Expedia.ca"
description: "Chebeague Island Vacation Rentals: find great deals on private apartments, homes, villas, cottages and other vacation properties in Chebeague Island with Expedia.ca"
canonical: "https://www.expedia.ca/Chebeague-Island-Vacation-Rentals.d6046986.Travel-Guide-VacationRentals"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-13T08:48:12Z
---

Plan your trip

- [Chebeague Island Travel Guide](https://www.expedia.ca/Chebeague-Island.dx6046986)
- [Hotels in Chebeague Island](https://www.expedia.ca/Chebeague-Island-Hotels.d6046986.Travel-Guide-Hotels)
- [Flights to Chebeague Island](https://www.expedia.ca/Cheap-Flights-To-Chebeague-Island.d6046986.Travel-Guide-Flights)
- [Car Rentals in Chebeague Island](https://www.expedia.ca/Car-Rentals-In-Chebeague-Island.d6046986.Car-Rental-Guide)
- [Chebeague Island Vacation Packages](https://www.expedia.ca/Chebeague-Island.d6046986.Destination-Travel-Guides)

# Chebeague Island Vacation Rentals
![A calm harbor with several sailboats anchored in the water.](https://images.trvl-media.com/place/6046986/e3672dae-ca9d-401e-a41d-f9e424fba1ca.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

[Check prices for these dates, December 13–14, 2026](https://www.expedia.ca/Hotel-Search?regionId=6046986&startDate=2026-12-13&endDate=2026-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&sort=VACATION%5FRENTAL)

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## Our top choices for Chebeague Island vacation rentals

### [1\. Cabin w/ bath + kitchenette | Hot tub add-on - 03](https://www.expedia.ca/Freeport-Hotels-Modern.h95164444.Hotel-Information)

![A cabin with two chairs facing a fire pit, surrounded by trees.](https://images.trvl-media.com/lodging/96000000/95170000/95164500/95164444/c6cf607e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: Freeport
- Guest rating: 9.8/10 (Exceptional, 10 reviews)
- Price: CA $299, CA $476 total, includes taxes & fees, Nov 17 - Nov 18, for Our top choices for Chebeague Island vacation rentals
- Review: A lovely glamping facility with several different types of structure in a quiet, wooded area just a couple miles from downtown Freeport. They've built a beautiful spa with sauna, cold plunge, hot tub, and soaking pool, the unit we stayed in was bright and airy, had an outdoor fire pit. We stayed three nights, will definitely stop here again!, by Kirt v.

### [2\. Great suburban location close to town!](https://www.expedia.ca/Portland-Hotels-Great-Suburban-Location-Close-To-Town.h132977513.Hotel-Information)

![A compact living space with a sofa, a coffee table, a TV on a stand, a floor lamp, and a bookshelf.](https://images.trvl-media.com/lodging/133000000/132980000/132977600/132977513/e6df188f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Deering Center
- Guest rating: 9.4/10 (Exceptional, 6 reviews)
- Price: CA $93, CA $97 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Chebeague Island vacation rentals
- Review: We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :), by Kaley

### [3\. The Weldon Hotel](https://www.expedia.ca/Portland-Hotels-The-Weldone-Hotel.h107321604.Hotel-Information)

![A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/9fd24e5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Downtown Portland
- Guest rating: 9.8/10 (Exceptional, 131 reviews)
- Price: CA $260, CA $390 total, includes taxes & fees, Nov 29 - Nov 30, for Our top choices for Chebeague Island vacation rentals
- Review: It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things, by Branden

### [4\. Orchid Harbor, Bailey Island 3BR](https://www.expedia.ca/Bailey-Island-Hotels-Orchid-Harbor.h103524025.Hotel-Information)

![A rocky shoreline at sunset with calm water and distant land.](https://images.trvl-media.com/lodging/104000000/103530000/103524100/103524025/f2588ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Harpswell
- Guest rating: 10/10 (Exceptional, 13 reviews)
- Price: CA $246, CA $579 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Chebeague Island vacation rentals
- Review: Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again., by Jane D.

### [5\. Full sized home](https://www.expedia.ca/Harpswell-Hotels-Full-Sized-Home.h91823998.Hotel-Information)

![A wooden deck with outdoor seating and string lights.](https://images.trvl-media.com/lodging/92000000/91830000/91824000/91823998/cc7d4138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Harpswell
- Guest rating: 9.8/10 (Exceptional, 80 reviews)
- Price: CA $285, CA $497 total, includes taxes & fees, Dec 1 - Dec 2, for Our top choices for Chebeague Island vacation rentals
- Review: Great house! Enjoyed our stay very much. Comfortable, clean, and many nice extra touches i.e. games, books., by Jill J.

### [6\. Mere Point Sunrise Views at Eastern Shore!](https://www.expedia.ca/Brunswick-Hotels-Mere-Point-Sunrise-Views-At-Eastern-Shore.h103524009.Hotel-Information)

![A house with a stone pathway leading to the front door, surrounded by lush greenery and a lake view.](https://images.trvl-media.com/lodging/104000000/103530000/103524100/103524009/62d47a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Brunswick
- Guest rating: 9.8/10 (Exceptional, 10 reviews)
- Price: CA $172, CA $496 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Chebeague Island vacation rentals
- Review: This little spot was an ideal getaway for our family’s summer trip to Maine. We very much enjoyed the porch with a view of the water and felt right at home here., by James C.

### [7\. Evalina Hotel](https://www.expedia.ca/Portland-Hotels-Evalina-Hotel.h126489510.Hotel-Information)

![A multi-story building with a stone facade, large windows, and a flat roof with dormer windows.](https://images.trvl-media.com/lodging/127000000/126490000/126489600/126489510/1998a918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Downtown Portland
- Guest rating: 10/10 (Exceptional, 19 reviews)
- Price: CA $324, CA $567 total, includes taxes & fees, Dec 14 - Dec 15, for Our top choices for Chebeague Island vacation rentals
- Review: Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland., by Eric

### [8\. Sunny Spot with Private Parking](https://www.expedia.ca/South-Portland-Hotels-Sunny-Spot-With-Private-Parking.h106377797.Hotel-Information)

![A sandy beach with people and a play structure.](https://images.trvl-media.com/lodging/107000000/106380000/106377800/106377797/e4150ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Knightville
- Guest rating: 9.8/10 (Exceptional, 38 reviews)
- Price: CA $143, CA $282 total, includes taxes & fees, Nov 15 - Nov 16, for Our top choices for Chebeague Island vacation rentals
- Review: Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic., by Greg Z.

### [9\. Glamping cabin w/ full bath | Hot tub add-on - 21](https://www.expedia.ca/Freeport-Hotels-Modern.h93377196.Hotel-Information)

![A cabin with a fire pit and outdoor seating.](https://images.trvl-media.com/lodging/94000000/93380000/93377200/93377196/aa1f059b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: CA $299, CA $476 total, includes taxes & fees, Nov 17 - Nov 18, for Our top choices for Chebeague Island vacation rentals

### [10\. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland](https://www.expedia.ca/Portland-Hotels-Charming-Studio-Apartment-With-WiFi.h114768499.Hotel-Information)

![A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.](https://images.trvl-media.com/lodging/115000000/114770000/114768500/114768499/b3ca2cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Munjoy Hill
- Guest rating: 9.4/10 (Exceptional, 32 reviews)
- Price: CA $178, CA $298 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Chebeague Island vacation rentals
- Review: Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!, by Ryan B.

### [11\. Portland 1-bedroom with enclosed porch & parking](https://www.expedia.ca/Portland-Hotels-Private-Entrance-Residential-Portland.h114761464.Hotel-Information)

![A narrow hallway with wooden flooring leading to a bedroom with a bed and a nightstand.](https://images.trvl-media.com/lodging/115000000/114770000/114761500/114761464/b844c6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Deering Center
- Guest rating: 7.8/10 (Good, 19 reviews)
- Price: CA $97, CA $102 total, includes taxes & fees, Nov 15 - Nov 16, for Our top choices for Chebeague Island vacation rentals
- Review: Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!, by Cricket C.

### [12\. Willard By the Sea - 30 ft to the beach- 2nd floor](https://www.expedia.ca/South-Portland-Hotels-Ocean-Views-30-Steps-To-Willard-Beach-Amazing-Location-5-7-Min-To-Portland.h93447451.Hotel-Information)

![A beach with clear water, people swimming, and houses in the background.](https://images.trvl-media.com/lodging/94000000/93450000/93447500/93447451/da261497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Willard
- Guest rating: 10/10 (Exceptional, 16 reviews)
- Price: CA $207, CA $589 total, includes taxes & fees, Nov 17 - Nov 18, for Our top choices for Chebeague Island vacation rentals
- Review: Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach., by Gerald B.

### [13\. Peaceful & minutes from Old Port w/private parking](https://www.expedia.ca/South-Portland-Hotels-Peaceful-Minutes-From-Old-Port-Wprivate-Parking.h113674508.Hotel-Information)

![A beach with people, a play structure, and a view of the sea.](https://images.trvl-media.com/lodging/114000000/113680000/113674600/113674508/cebce8b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Knightville
- Guest rating: 9.8/10 (Exceptional, 14 reviews)
- Price: CA $172, CA $335 total, includes taxes & fees, Nov 15 - Nov 16, for Our top choices for Chebeague Island vacation rentals
- Review: Cute, convenient spot!, by Kelly S.

### [14\. Casco Bay Oceanfront Retreat by Everrow](https://www.expedia.ca/Freeport-Hotels-Waterfront-Casco-Bay-Gem.h132993735.Hotel-Information)

![A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.](https://images.trvl-media.com/lodging/133000000/133000000/132993800/132993735/1d3fc6ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Guest rating: 10/10 (Exceptional, 13 reviews)
- Price: CA $536, CA $1,225 total, includes taxes & fees, Nov 30 - Dec 1, for Our top choices for Chebeague Island vacation rentals
- Review: The house was amazing. We would recommend this property to anyone. The view, stars at night and accessibility to where we wanted to visit, was perfect., by Vanessa K.

### [15\. Arlie\`s Digs - Willard Beach by Everrow](https://www.expedia.ca/South-Portland-Hotels-Arlies-Digs-One-Block-To-Willard-Beach.h81627464.Hotel-Information)

![A beach with a wooden chair and a small building in the background.](https://images.trvl-media.com/lodging/82000000/81630000/81627500/81627464/1bda7694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Willard Beach
- Guest rating: 10/10 (Exceptional, 73 reviews)
- Price: CA $262, CA $605 total, includes taxes & fees, Nov 30 - Dec 1, for Our top choices for Chebeague Island vacation rentals
- Review: Great stay!, by Jason M.

### [16\. Studio Apartment near downtown Walkable!](https://www.expedia.ca/Portland-Hotels-Studio-Apartment-In-Town-Walkable.h113410786.Hotel-Information)

![A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.](https://images.trvl-media.com/lodging/114000000/113420000/113410800/113410786/w990h1334x0y0-51987bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: West Bayside
- Guest rating: 8.2/10 (Very good, 27 reviews)
- Price: CA $84, CA $174 total, includes taxes & fees, Dec 3 - Dec 4, for Our top choices for Chebeague Island vacation rentals
- Review: Location was convenient to everything and building was super secure., by Rose

### [17\. Mid Coast Getaway w/ water views](https://www.expedia.ca/Phippsburg-Hotels-Mid-Coast-Getaway-W-Water-Views.h114893070.Hotel-Information)

![A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.](https://images.trvl-media.com/lodging/115000000/114900000/114893100/114893070/594f2bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: West Point
- Guest rating: 9.2/10 (Wonderful, 12 reviews)
- Price: CA $150, CA $289 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Chebeague Island vacation rentals
- Review: 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!, by Rebecca

### [18\. Heated Game Room, Coastal Maine Cape Sleeps 10](https://www.expedia.ca/Yarmouth-Hotels-Luxe-5BR3BA-Cape-Game-Room-20min-To-Portland.h128589867.Hotel-Information)

![A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.](https://images.trvl-media.com/lodging/129000000/128590000/128589900/128589867/68649f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Yarmouth
- Guest rating: 10/10 (Exceptional, 4 reviews)
- Price: CA $649, CA $1,296 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Chebeague Island vacation rentals
- Review: What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again., by Michelle T.

### [19\. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!](https://www.expedia.ca/Portland-Hotels-2-Bedroom-Apartment-Steps-From-Eastern-Prom-Walk-To-Everything.h133215210.Hotel-Information)

![A room with two wicker chairs, a potted plant, and a view of a body of water and buildings through large windows with blinds.](https://images.trvl-media.com/lodging/134000000/133220000/133215300/133215210/9f7c3fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Munjoy Hill
- Guest rating: 10/10 (Exceptional, 6 reviews)
- Price: CA $225, CA $585 total, includes taxes & fees, Nov 18 - Nov 19, for Our top choices for Chebeague Island vacation rentals
- Review: Lovely clean property in a really great location. Walkable to town center! Perfect !, by Anonymous traveller

### [20\. Modern cabin w/ full bath | Hot tub add-on - 19](https://www.expedia.ca/Freeport-Hotels-Modern.h93377193.Hotel-Information)

![A cabin with a fire pit and outdoor seating.](https://images.trvl-media.com/lodging/94000000/93380000/93377200/93377193/38acb842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Guest rating: 10/10 (Exceptional, 5 reviews)
- Price: CA $299, CA $476 total, includes taxes & fees, Nov 17 - Nov 18, for Our top choices for Chebeague Island vacation rentals
- Review: Great place, the Desert of Maine campground. The entire cabin was spotless. Great communication from the host, Doug. So wonderful for pets also. Quiet, clean & perfect. 5 stars. What a wonderful stay! If you are looking for a beautiful and peaceful get away, this is the place for you! You will not be disappointed. Doug is an awesome host!, by Kim L.

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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## Find vacation rentals that suit your style

[Cabins](https://www.expedia.ca/Hotel-Search?destination=Chebeague%20Island,%20Maine,%20United%20States%20of%20America&regionId=6046986&latLong=43.741663,-70.107487&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=CABIN)

[Cottages](https://www.expedia.ca/Hotel-Search?destination=Chebeague%20Island,%20Maine,%20United%20States%20of%20America&regionId=6046986&latLong=43.741663,-70.107487&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=COTTAGE)

[Chalets](https://www.expedia.ca/Hotel-Search?destination=Chebeague%20Island,%20Maine,%20United%20States%20of%20America&regionId=6046986&latLong=43.741663,-70.107487&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=CHALET)

[Apartments](https://www.expedia.ca/Hotel-Search?destination=Chebeague%20Island,%20Maine,%20United%20States%20of%20America&regionId=6046986&latLong=43.741663,-70.107487&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=APARTMENT)

[Aparthotels](https://www.expedia.ca/Hotel-Search?destination=Chebeague%20Island,%20Maine,%20United%20States%20of%20America&regionId=6046986&latLong=43.741663,-70.107487&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=APART%5FHOTEL)

[Condos](https://www.expedia.ca/Hotel-Search?destination=Chebeague%20Island,%20Maine,%20United%20States%20of%20America&regionId=6046986&latLong=43.741663,-70.107487&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=CONDO)

## Top Chebeague Island Hotel Reviews

### [Spark by Hilton Freeport](https://www.expedia.ca/Freeport-Hotels-Spark-By-Hilton-Freeport.h894042.Hotel-Information)

![A room with a green carpet, two rocking chairs, a small table with a potted plant, a window with a view of greenery, and a coffee station with dispensers.](https://images.trvl-media.com/lodging/1000000/900000/894100/894042/w5755h3840x5y0-437f82ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: Entièrement rénové. Très bonne insonorisation. Simple mais très bien, by Sophie, September 30, 2026, rated 10/10 Excellent

### [The Harraseeket Inn & Event House Freeport Downtown](https://www.expedia.ca/Portland-Hotels-Harraseeket-Inn.h51266260.Hotel-Information)

![A two-story building with a large glass conservatory and yellow umbrellas in the garden area.](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/b990d573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: Another lovely stay. Beautiful property, overflowing with flowers. Comfortable rooms. Hearty breakfast., by Aaron, October 1, 2026, rated 10/10 Excellent

### [Hampton Inn Freeport/Brunswick](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-FreeportBrunswick.h281934.Hotel-Information)

![A hotel lobby with a seating area, a snack bar, and a refrigerator.](https://images.trvl-media.com/lodging/1000000/290000/282000/281934/88ff60eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: Nice touch .. barn door make sense when planning utilizing a small space .. haven’t seen that before! Pleasant staff.. great price … in off season … we have paid lots more to stay at Hampton inns during high season, by Nancy, November 12, 2026, rated 10/10 Excellent

### [The James Place Inn B&B](https://www.expedia.ca/Portland-Hotels-The-James-Place-Inn-Bed-And-Breakfast.h1489274.Hotel-Information)

![A house with a sign for The James Place Inn, indicating a vacancy.](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/736db751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: It was great ! The hosts were friendly and receptive to our needs. You can feel the extra care they give to making you feel at home. And breakfast was amazing. They even take special requests., by Eugenia, July 24, 2024, rated 10/10 Excellent

### [The Kendall Inn](https://www.expedia.ca/Portland-Hotels-Kendall-Tavern-Inn.h1512059.Hotel-Information)

![A covered porch with white railings and a view of a well-maintained lawn and pathway.](https://images.trvl-media.com/lodging/2000000/1520000/1512100/1512059/bce07578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: Wonderful host. Excellent breakfast. Bed was very comfortable. I recommend., by Eric, August 6, 2025, rated 10/10 Excellent

### [The Orchard House: Inn & Cafe](https://www.expedia.ca/Portland-Hotels-The-Orchard-House-Cafe.h19561353.Hotel-Information)

![A black front door with a light fixture above it, flanked by two potted evergreen trees.](https://images.trvl-media.com/lodging/20000000/19570000/19561400/19561353/1161f28b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: Beautiful place. Rooms were exceptionally lovely. Staff also!, by Janne, June 26, 2022, rated 10/10 Excellent

### [Embassy Suites by Hilton Portland Maine](https://www.expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information)

![A spacious lobby with multiple seating areas, a fireplace, and large windows.](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/6b6e052e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Portland
- Review: Rien à dire, by Suke Diadibwa, August 27, 2026, rated 10/10 Excellent

### [Candlebay Inn](https://www.expedia.ca/Portland-Hotels-Candlebay-Inn.h11484573.Hotel-Information)

![A dining area with wooden tables and chairs, a chandelier, and a kitchen in the background.](https://images.trvl-media.com/lodging/12000000/11490000/11484600/11484573/0117cb35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Freeport
- Review: Nice clean air conditioned room and great homemade breakfast included in the stay, by William, August 9, 2025, rated 10/10 Excellent

### [Portland Harbor Hotel](https://www.expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information)

![An outdoor patio with wicker furniture, a stone fireplace, and string lights.](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/e9f78f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Downtown Portland
- Review: We absolutely loved this hotel. The location was perfect for our ladies trip. The staff were beyond helpful!!! And the rooms were very well maintained. thank you very much….., by Barbara, September 28, 2026, rated 10/10 Excellent

### [AC Hotel Portland Downtown/Waterfront, ME](https://www.expedia.ca/Portland-Hotels-AC-Hotel-By-Marriott-Portland-DowntownWaterfront.h22514704.Hotel-Information)

![A modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514704/f9c45283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Downtown Portland
- Review: Nice hotel! Room was clean and the hotel is well located., by Nicole Emily Elizabeth, August 22, 2026, rated 10/10 Excellent

### [Inn By The Sea](https://www.expedia.ca/Portland-Hotels-Inn-By-The-Sea.h1542725.Hotel-Information)

![A beach with several blue umbrellas and lounge chairs.](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Cape Elizabeth
- Review: House by the beach vibe. Calm and quiet. Very relaxing, we loved it!!, by Anonymous traveller, June 25, 2019, rated 10/10 Excellent

### [The Brunswick Hotel](https://www.expedia.ca/Boothbay-Harbor-Hotels-The-Brunswick-Hotel.h4449120.Hotel-Information)

![An outdoor patio with seating, a fire feature, and string lights.](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/3069046e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Brunswick
- Review: I had such a lovely stay at The Brunswick Hotel during our autumn road trip through New England! Its warm, inviting atmosphere and charming location made it a wonderful place to experience Maine in the fall. The hotel was comfortable and welcoming, and I especially appreciated being able to share the experience with my dog, Auggie. A lovely stay in a charming New England town that I would happily return to!, by Sok, October 26, 2026, rated 10/10 Excellent

### [The Federal](https://www.expedia.ca/Brunswick-Hotels-The-Federal.h75630171.Hotel-Information)

![A spacious living area with a curved staircase, a round glass coffee table, and a seating arrangement.](https://images.trvl-media.com/lodging/76000000/75640000/75630200/75630171/282b074c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Brunswick
- Review: Very comfortable, clean, spacious room and hotel in easy walking distance to downtown Brunswick. We enjoyed the optional bagged breakfast with fruit, yogurt, and a pastry, which hit the spot and was a good value., by Catherine, January 5, 2026, rated 10/10 Excellent

## 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](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chebeague Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chebeague Island vacation rentals we have selected for you start as low as CA $83 per night. Entering your travel dates in the search wizard 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?

[The Perfect Beach Escape: Cozy 4-Bedroom Retreat](https://www.expedia.ca/Portland-Hotels-A-Beautiful-Ocean-View-Cottage-Come-Enjoy-The-Wonderful-Beach.h66466820.Hotel-Information): 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.

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