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Our top choices for Chebeague Island apartments

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
9.0 out of 10, Wonderful, (8 reviews)
"The views from the home were amazing! The home was cozy and had everything we needed for our stay. The host was great with communication and quick to reply. We were very happy with our stay and are grateful for the ability to stay here."
United States
Elizabeth M.
The price is AED 288
AED 697 total
includes taxes & fees
16 Nov - 17 Nov
Sunset Hideaway on Bailey Island

2. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"The bed was the most comfortable I have ever slept on! Lovely large warm open room. I appreciated the coffee/tea options, and the condiments in the fridge. There was a white noise machine in the room though we did not use it."
United States
Susan S.
The price is AED 253
AED 545 total
includes taxes & fees
16 Nov - 17 Nov
Studio Apartment in Freeport

3. Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Harpswell
10.0 out of 10, Exceptional, (3 reviews)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
The price is AED 569
AED 1,157 total
includes taxes & fees
15 Nov - 16 Nov
Bird Watching Paradise @ Waterfront Harpswell with Private Deck

4. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"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 :)"
United States
Kaley
The price is AED 239
AED 287 total
includes taxes & fees
12 Nov - 13 Nov
Great suburban location close to town!

5. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is AED 369
AED 756 total
includes taxes & fees
12 Nov - 13 Nov
Sunny Spot with Private Parking

6. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (19 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is AED 251
AED 263 total
includes taxes & fees
15 Nov - 16 Nov
Portland 1-bedroom with enclosed porch & parking

7. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (27 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
The price is AED 216
AED 440 total
includes taxes & fees
12 Nov - 13 Nov
Studio Apartment near downtown Walkable!

8. 2-story stay w/ king bed and private deck

2-story stay w/ king bed and private deck
Deering Center
6.0 out of 10, (2 reviews)
"Clean, comfortable bed, and a good location. Kitchen items and towels were very minimal. No extras! Also, bedroom is on the second floor and the one bathroom is on the first. "
United States
Mary P.
The price is AED 251
AED 263 total
includes taxes & fees
16 Nov - 17 Nov
2-story stay w/ king bed and private deck

9. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!"
United States
Ryan B.
The price is AED 459
AED 769 total
includes taxes & fees
16 Nov - 17 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

10. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (14 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AED 444
AED 863 total
includes taxes & fees
15 Nov - 16 Nov
Peaceful & minutes from Old Port w/private parking

11. Walkable near downtown 1 Bedroom

Walkable near downtown 1 Bedroom
West Bayside
4.6 out of 10, (8 reviews)
"This room was actually a scary experience. The area was desolate, located across from a huge parking lot with drug addicts surrounding the building. The Uber driver would not leave until I entered because he felt I was unsafe, especially at midnight. The electric locks on both the front door and my room door did not feel secure. There was no deadbolt inside the room for extra security, so I wedged a chair under the door handle to feel safe. Considering the constant commotion outside and the...
United States
Farah
The price is AED 231
AED 431 total
includes taxes & fees
16 Nov - 17 Nov
Walkable near downtown 1 Bedroom

12. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (16 reviews)
"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."
United States
Gerald B.
The price is AED 555
AED 1,528 total
includes taxes & fees
17 Nov - 18 Nov
Willard By the Sea - 30 ft to the beach- 2nd floor

13. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is AED 215
AED 503 total
includes taxes & fees
17 Nov - 18 Nov
Bright & Spacious Apartment with Amazing Shower

14. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AED 215
AED 471 total
includes taxes & fees
15 Nov - 16 Nov
Beautiful 1st Floor Apartment & Amazing Shower

15. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
Munjoy Hill
10.0 out of 10, Exceptional, (6 reviews)
"Lovely clean property in a really great location. Walkable to town center! Perfect !"
United States
Anonymous traveler
2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

16. King Size Bed ♦ West End Studio ♦ Walk to Old Port

King Size Bed ♦ West End Studio ♦ Walk to Old Port
West End
9.6 out of 10, Exceptional, (4 reviews)
"Super clean. Exactly as advertised. Perfect location in a quiet neighborhood on the West End."
United States
Maureen R.
The price is AED 391
AED 899 total
includes taxes & fees
2 Dec - 3 Dec
King Size Bed ♦ West End Studio ♦ Walk to Old Port

17. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring and visiting Portland! Great communication, easy process, and would definitely stay again if we visit Franklin"
United States
Jordan M.
East end. Walk to food, beer and downtown fun.

18. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (11 reviews)
"Great spot. Roomy. Close to shops and ferries. It had everything we needed to see Portland."
United States
Benton M.
The price is AED 726
AED 1,360 total
includes taxes & fees
2 Dec - 3 Dec
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

19. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (7 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
The price is AED 915
AED 1,401 total
includes taxes & fees
17 Nov - 18 Nov
East End Guesthouse

20. 1200 sq ft ♦ West End Gem ♦ Steps from Old Port

1200 sq ft ♦ West End Gem ♦ Steps from Old Port
West End
9.2 out of 10, Wonderful, (110 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
1200 sq ft ♦ West End Gem ♦ Steps from Old Port
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.

Learn more about Chebeague Island

Rent bikes to explore this peaceful island's rocky beaches and historic 1920s inn, where fresh lobster awaits. Take the passenger ferry from Cousins Island for a day trip, then kayak along the quiet coastline or hike wooded trails.

A calm harbor with several sailboats anchored in the water.

Top reviews in Chebeague Island

Frequently Asked Questions

What's it like to stay at an apartment in Chebeague Island?

There are 9 hotels and other accommodations in Chebeague Island. Though there aren't many apartments, we can help you locate similar accommodations. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. You can even filter by similar property types like condos, vacation homes, or cottages.

Why choose apartments instead of traditional hotels?

Offering a kitchen for convenient meals, an apartment is often more spacious than a traditional hotel room. Apartments are a good option for couples who want a more local feel, but also for families wanting the conveniences of home.

What's the top apartment I should consider for a stay in Chebeague Island?

Here's a popular apartment in the area to consider: Oceanfront Studio w/ Private Dock in Harpswell!: Located 9.4 mi/15.1 km away in Harpswell. Amenities include private patios.

What will the weather be like in Chebeague Island?

Though weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Chebeague Island. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chebeague Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.

What should I see 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's the best way to get to and around Chebeague Island?

Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Portland Intl. Jetport Airport (PWM), which is located 12.1 mi (19.4 km) from the city center. Otherwise, look for flights into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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