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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 306 Apartments in Chebeague Island with updated reviews, rates, and availability.

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (144)
"Old friends (in age and longevity of relationships) met up in Portland for a weekend getaway. Great location. Great city. Enjoyed our time exploring the city culture and restaurants within easy reach but also spent long hours in the bright living room catching up over a pit of tea."
The price is AED 364
AED 813 total
includes taxes & fees
26 Feb - 27 Feb
Glorious getaway on Portland's Eastern Promenade.
Fall In Love With Portland!
Living area

Fall In Love With Portland!

9.6 out of 10, Exceptional, (110)
"We had a great time at Nick's apartment, it is spaceous and tastefully furnished. We were able to feel right at home and used the kitchen every day, the dining room had space for all of us which made for some great holiday meals together. The location is nearly unbeatable with just two blocks to the promenade by the water and a short walk to downtown. Congress Street, which is 50 yards from the front door, has a really cool vibe with bars, cafes and restaurants. Yet, you are clearly nestled in a...
The price is AED 731
AED 1,818 total
includes taxes & fees
24 Feb - 25 Feb
Fall In Love With Portland!
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is AED 356
AED 693 total
includes taxes & fees
24 Feb - 25 Feb
Adorable Portland getaway on the Eastern Promenade
1 room luxury ocean front studio cottage
Terrace/patio

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage
Cozy West End apartment minutes from the Old Port
Private kitchen

Cozy West End apartment minutes from the Old Port

10.0 out of 10, Exceptional, (6)
"This place was absolutely adorable and was conveniently located close to everything we needed."
The price is AED 448
AED 829 total
includes taxes & fees
24 Feb - 25 Feb
Cozy West End apartment minutes from the Old Port
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Living area

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (103)
"A great place for people looking to explore Portland. Clean, comfortable and with great communication by our host, we’d recommend it for any group looking for a home base in the area."
The price is AED 731
AED 1,818 total
includes taxes & fees
24 Feb - 25 Feb
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Charming West End Hideaway. Private Parking
Room

Charming West End Hideaway. Private Parking

10.0 out of 10, Exceptional, (24)
"Communication with the owner was seamless and there were no details missed. The location was perfect for going out and also great if you're looking to shop. The apartment was clean and adorable with a little private balcony. Would definitely stay again!"
The price is AED 360
AED 717 total
includes taxes & fees
24 Feb - 25 Feb
Charming West End Hideaway. Private Parking
Completely remodeled 2 bedroom apartment in Portland's West End
Living area

Completely remodeled 2 bedroom apartment in Portland's West End

10.0 out of 10, Exceptional, (60)
"We had a very nice stay in this apartment. I would definitely recommend it to others. The owners were friendly and it was easy to get into the unit. The only drawback for anyone who's not quite so agile is the steep staircase to get to the bedrooms. It worked out fine for our family of four, so I just list this for anyone with mobility issues."
Completely remodeled 2 bedroom apartment in Portland's West End
Incredible Location! Heart of Old Port|Roomy Condo

Incredible Location! Heart of Old Port|Roomy Condo

10.0 out of 10, Exceptional, (25)
"Great location for a fun Old Port get away. Property manager was very responsive."
Incredible Location! Heart of Old Port|Roomy Condo
The Portland Getaway
Private kitchen

The Portland Getaway

9.6 out of 10, Exceptional, (21)
"This property is well maintained and very clean . Host was easy to communicate with and it was well stocked with basic needs. "
The Portland Getaway
Bright & Sunny West End Apartment with Private Parking.
Dining

Bright & Sunny West End Apartment with Private Parking.

9.8 out of 10, Exceptional, (23)
"This third floor apartment was conveniently located to downtown Portland. There are lots of good restaurants within walking distance. It was spacious and well equipped. It only came with 1 parking space but my son was able to find a spot nearby on the street."
The price is AED 650
AED 1,161 total
includes taxes & fees
2 Mar - 3 Mar
Bright & Sunny West End Apartment with Private Parking.
Beautiful Old Port Apt-Downtown

Beautiful Old Port Apt-Downtown

9.6 out of 10, Exceptional, (14)
"It was all terrific. There was one issue with the apartment on the last night but they responded promptly and while it could not be fixed because of the holiday they were attentive and apologetic."
The price is AED 1,197
AED 2,340 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful Old Port Apt-Downtown
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

9.8 out of 10, Exceptional, (16)
"Extremely clean, modern and great locattion"
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
Historic Home in the West End. Private Parking.
Room

Historic Home in the West End. Private Parking.

9.8 out of 10, Exceptional, (28)
"We had a lovely stay in this historic home. The decor is charming and original, beds are comfy and everything is clean. The neighborhood is attractive and quiet. The information from the host was helpful. It was great to have a dedicated parking space. As described, the kitchenette has no sink but otherwise is very well equipped for simple food/beverage preparation. We look forward to staying in the future."
The price is AED 437
AED 881 total
includes taxes & fees
24 Feb - 25 Feb
Historic Home in the West End. Private Parking.
Chic One Bedroom Apartment In Portland's Arts District
Welcome to our Chic One Bedroom at Portland on Avon!

Chic One Bedroom Apartment In Portland's Arts District

10.0 out of 10, Exceptional, (203)
"Sue and Barry were so accommodating, we have never been treated so well staying at a VRBO. They showed us local spots, told us great places for food and drinks, extremely kind and knowledgeable of the area. Couldn’t recommend them enough! "
Chic One Bedroom Apartment In Portland's Arts District
Harborview - Curated East End Escape w/ Parking
Dining

Harborview - Curated East End Escape w/ Parking

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay at Jennifer’s place very much .The location was excellent. Walkable distance to the city center and to all the best restaurants.The view was breathtaking and the apartment was amazing!We highly recommend this place. We hope to return soon!"
The price is AED 1,275
AED 2,174 total
includes taxes & fees
24 Feb - 25 Feb
Harborview - Curated East End Escape w/ Parking
East end. Walk to food, beer and downtown fun.

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

9.8 out of 10, Exceptional, (23)
"Our host was an excellent, prompt communicator. He even offered information about things to do in the area. He was very clear about expectations about our stay which at first was a little off-putting. Cooking no greasy food seemed a little much and had us wondering what was allowed. The property was well stocked and as described including the slanted floor. We weren’t aware at booking that parking was only on the street. That would have been nice to know. It’s a 20 minute walk to downtown which...
The price is AED 1,120
AED 1,749 total
includes taxes & fees
15 Mar - 16 Mar
East end. Walk to food, beer and downtown fun.
Old Orchard Beach Apartment - Quick Walk to Beach!
Old Orchard Beach Vacation Rental | Top-Floor Apartment | 1BR | 1BA | 650 Sq Ft

Old Orchard Beach Apartment - Quick Walk to Beach!

9.4 out of 10, Exceptional, (20)
"Great location to walk to the beach or to the pier. The top floor requires many steps so if you have a hard time with mobility this would not work for you. We loved it! So clean and well stocked with dishes, appliances and cookware. The recliners are the bomb! Bed was comfortable as well. Two air conditioners which kept us comfortable. The site is on point with their description and photos."
Old Orchard Beach Apartment - Quick Walk to Beach!
Superb Location!! Heart of Old Port/Spacious Condo

Superb Location!! Heart of Old Port/Spacious Condo

9.8 out of 10, Exceptional, (19)
"This was our second stay at Dena’s property. Perfect size, 3bedrooms and 3 baths. This unit is impeccable, very clean, spacious, and well stocked. Dena checked in with us to be sure we were able to check in easily and was very responsive to anything we needed. We were located in the center of everything. Easily walkable area. We loved our stay and would love to return! "
Superb Location!! Heart of Old Port/Spacious Condo
Spacious Central Beautiful Apt: 4 Bedrooms, 5 Beds & 2 free parking.
Living area

Spacious Central Beautiful Apt: 4 Bedrooms, 5 Beds & 2 free parking.

10.0 out of 10, Exceptional, (15)
"The house is in great condition and is decorated nicely. Joel is kind and really accommodating. It is super close to some fun, trendy spots but I would suggest keeping a buddy system if you’re walking along the street at night (similar to any city). It’s a great spot for big groups!"
Spacious Central Beautiful Apt: 4 Bedrooms, 5 Beds & 2 free parking.
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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Other property types in Chebeague Island

The Weldon Hotel
Front of property

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (36)
"Overall, the stay was great. The lower-level suite was a bit noisy, as we were at ground level; however, I would highly recommend staying here if you are looking for full amenities and a short commute to everything in downtown Portland. "
The price is AED 534
AED 582 total
includes taxes & fees
6 Mar - 7 Mar
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views
100 feet from the ocean 3 bedroom cottage 420 friendly
Beach

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
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.

Frequently asked questions

What's it like to stay at an apartment in Chebeague Island?
There are 10 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?
Listed below are some of the favorite apartments in the area to choose from: Adorable Portland getaway on the Eastern Promenade: Situated in Portland, 8.6 mi/13.9 km from the heart of Chebeague Island. Includes free WiFi, private patios, and Smart TVs. Glorious getaway on Portland’s Eastern Promenade.: Located 8.6 mi/13.8 km away in Portland. Free WiFi, separate dining areas, and Smart TVs are included. 1 room luxury ocean front studio cottage: It’s situated in Harpswell, 6.6 mi/10.6 km away. Includes outdoor space and sofa beds. Historic Home in the West End. Private Parking.: 9.9 mi/16 km away in Portland. Free WiFi and Smart TVs are included. Fall In Love With Portland!: It’s located in Portland, 8.6 mi/13.8 km from Chebeague Island. Includes free WiFi, private patios, and separate dining areas.
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 Paddleworks, or get out into nature at a spot like Wolfe’s Neck Woods State Park. Bailey Island Bridge and Casco Bay 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.