Chebeague Island Vacation Rentals

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Vacation Rentals in Chebeague Island

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (38)
"Very clean and comfortable! "
The price is CA $208
CA $227 total
includes taxes & fees
Mar 6 - Mar 7
The Weldon Hotel

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

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

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (124)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is CA $122
CA $320 total
includes taxes & fees
Mar 3 - Mar 4
Oceanfront Condo! Spectacular Views From Private Large Balcony

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (198)
"Great codo unit, very close to everything "
The price is CA $251
CA $480 total
includes taxes & fees
Mar 2 - Mar 3
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.4 out of 10, Exceptional, (26)
"This 2 bedroom cottage was perfect for our 3 day stay.Location was a 10 minute walk to the boardwalk.Would like to come back in the summer."
The price is CA $142
CA $309 total
includes taxes & fees
Mar 3 - Mar 4
Large 2BD cottage 10 min to Pier & Beach Pets ok

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is CA $139
CA $269 total
includes taxes & fees
Mar 2 - Mar 3
Adorable Portland getaway on the Eastern Promenade

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (30)
"This property was spectacular! Beautiful views, clean, spacious and comfortable. Great space to share with a larger group. The Host was very responsive. It was an amazing experience even in the winter. "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (40)
"Great place.... Very clean and everything you will need to stay. It was three levels and it had supplies needed for the beach (Beach wagon, chairs, towel, sand toys...). We stayed off season so most of the houses were vacant. We would definately come back again. I did send two messages to the owner, but did not get a response. "
The price is CA $213
CA $703 total
includes taxes & fees
Mar 1 - Mar 2
Beach House ∆ Prime Location ∆ Steps to the Ocean

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (13)
"This cabin is something incredibly singular and special. It is imbued with the legacy of the Hall family, and you can read their history as you explore the house. The view is unbelievable - waking up, going downstairs, and being that close to the ocean is so peaceful. We could have spent a month reading as nearly every room is a library. The kitchen is stocked with some great old cast irons and lobster pots for whatever one would need. The China and dining wear even had character and...
Oceanfront Cabin-Castle in Maine Woods

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (145)
"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 CA $196
CA $378 total
includes taxes & fees
Mar 2 - Mar 3
Glorious getaway on Portland's Eastern Promenade.

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

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Very clean. Nice walk along bikepath to downtown. Will look to stay here again. Loved the neighborhood and parking was easy. Kitchen had everything we needed to cook. "
The price is CA $287
CA $513 total
includes taxes & fees
Mar 2 - Mar 3
Cozy, Elegant and Bright 2 bed in the East End

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (212)
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness. "
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (99)
"Very comfortable, close to shopping and restaurants, clean, easily accessible"
The price is CA $215
CA $439 total
includes taxes & fees
Mar 3 - Mar 4
City Amenities, Casco Bay Sunrises and Natural Beauty

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

9.6 out of 10, Exceptional, (55)
"Beautiful house with lots of space. Comfortable and easy check in. Great area too"
The price is CA $859
CA $1,776 total
includes taxes & fees
Mar 2 - Mar 3
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

68 East Grand Ave

3.0 star property
8.8 out of 10, Excellent, (3)
"Overall good. Was told we could not stand in the Parking lot, and checkout instructions were vague. But a fabulous location- everything in walking distance! And very clean!"
68 East Grand Ave

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
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 types of properties in Chebeague Island you may be interested in

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1005)
"Such a great place to getaway and relax. Very hospitable and clean. Food was perfect along with some of the best service around. 10/10 I’d rate . "
The price is CA $141
CA $158 total
includes taxes & fees
Mar 16 - Mar 17
The Westin Portland Harborview

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1464)
"Amazing hotel "
The price is CA $176
CA $250 total
includes taxes & fees
Mar 16 - Mar 17
Portland Harbor Hotel

DoubleTree by Hilton Hotel Portland

4.0 star property
8.0 out of 10, Very good, (1113)
"Congested area"
The price is CA $107
CA $117 total
includes taxes & fees
Mar 2 - Mar 3
DoubleTree by Hilton Hotel Portland
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

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 Globe House on Munjoy Hill - Walk to Breweries: This vacation home near Chebeague Island is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 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 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.