Search Vacation Homes in Chebeague Island

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Compare 495 Vacation Homes in Chebeague Island with updated reviews, rates, and availability.

Orchard Beach Elegance: Spacious Yard & Patio
10.0 out of 10, Exceptional, (10)
"We rented this property for our 6 year anniversary and it was even better than we were expecting! Great location with the perfect amount of privacy. Highly recommend this location for families and couples! "
Orchard Beach Elegance: Spacious Yard & Patio
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very Good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Dining
One queen bed unit 16 at Belkis beach motel
6.8 out of 10, (3)
"We have stayed here twice and it work perfect for us. Close to the beach and convenient. Staff are friendly and accommodating. Will stay here again."
One queen bed unit 16 at Belkis beach motel
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Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is SAR 743
SAR 1,761 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Elegant condo - walk to Portland's best restaurants & Old Port
Unit A - front deck
Walk to the Beach | Back Yard | EV Charger | Unit A in Duplex
Walk to the Beach | Back Yard | EV Charger | Unit A in Duplex
Exterior
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
10.0 out of 10, Exceptional, (37)
"What a wonderful home in a fantastic location! It has everything you need for a getaway: open and inviting communal spaces including a spacious wraparound deck, stocked kitchen for meals, comfy beds, working fireplace, and so much more. Wouldn't hesitate to stay again!"
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
Seaside Splendor: 4BR House Close to Beach & Pier
9.6 out of 10, Exceptional, (12)
"This property worked out great for 4 of my employees to stay while working on a video surveillance installation at a local car dealership."
Seaside Splendor: 4BR House Close to Beach & Pier
Contemporary Comfort: Game Room & Portland Access
Contemporary Comfort: Game Room & Portland Access
Renovated 4 BD | Sleeps 9 | Amazing Backyard Area
10.0 out of 10, Exceptional, (4)
"House is beautiful!! Love the decor! Very spacious,clean and fit all of our needs for 6 adults and 2 children! Kids loved the toys that were there!!"
Renovated 4 BD | Sleeps 9 | Amazing Backyard Area
Private kitchen
beautiful rooms at Belkis Beach Motel
6.8 out of 10, (16)
"Overall okay experience. Spent more time away from motel."
beautiful rooms at Belkis Beach Motel
Walkway around the corner to the beach !
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, (110)
"Good location, owner was very responsive to our needs."
East Grand Ave Fabulous Cottage
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.8 out of 10, Excellent, (48)
"This was a great old townhouse. Great parking and very clean. Easy walk to attractions and a charming neighborhood bar just around the corner. "
The price is SAR 458
SAR 969 total
includes taxes & fees
3 Jum. II - 4 Jum. II
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Living room with oversized leather reclining couch, recliner and 60" smart tv
Convenient Portland home 3 miles from Downtown
10.0 out of 10, Exceptional, (8)
"The house was spotless and comfortable. We arrived in the middle of a snowstorm, and it was great to have the one-car attached garage, a heating system that worked well, someone who plowed the driveway and shoveled the snow shortly after we arrived, and a comfortable hot shower. Grocery stores and restaurants are nearby. Beds are comfortable, and there is a lot of closet space and drawer space. We would stay here again."
The price is SAR 836
SAR 2,420 total
includes taxes & fees
30 Jum. I - 31 Jum. I
Convenient Portland home 3 miles from Downtown
Third or top floor lounge- spectacular ocean views.
Sunrise Catcher with a Panoramic View!
10.0 out of 10, Exceptional, (23)
"The property is absolutely beautiful with stunning views! Every thing was accurate on the website. A perfect spot for 3 couples as each bedroom is on a separate floor. The kitchen was well appointed and the beds very comfortable. Sitting on the main deck with coffee enjoying the ocean each morning was the highlight of the experience. A quintessential Maine experience! We will definitely seek out this property in the future for a return visit!"
Sunrise Catcher with a Panoramic View!
Private kitchen
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (115)
"Perfect little place just outside of downtown, very convenient to everything. Very clean & nicely decorated. Exactly as shown. Excellent communication from host, easy check in. Will def re-book if/when we return to Portland!"
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
It’s going to be an amazing summer!
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
10.0 out of 10, Exceptional, (20)
"The property and home were very charming, lovely views from every room of the tawny late November marsh landscape. Recent renovations provided creature comforts, and getting out to explore in-town Bath or out to Reid was a short car ride away. Accessibility for older family was great with the single level and low entry thresholds. Tina was great for communicating with- our best wishes!"
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
Gorgeous dining table for six
On Par for the Beach | New Build | Golf Course| Bayley Vacation Rentals
On Par for the Beach | New Build | Golf Course| Bayley Vacation Rentals
Dining
New home at Popham Beach
10.0 out of 10, Exceptional, (5)
"Wonderful way to decompress and walk the sandy beaches at Popham. The property, the views, our host, and all details were great!"
New home at Popham Beach
Topsham Vacation Rental | 2BR | 1BA | 775 Sq Ft | Step-Free Access
Riverfront Topsham Home ~ 28 Mi to Portland!
4.0 out of 10, (1)
Riverfront Topsham Home ~ 28 Mi to Portland!
Exterior
Five miles from the beach, newly remodeled home with lots of privacy.
10.0 out of 10, Exceptional, (34)
"We came up for the 2024 UNE Commencement in Portland and needed enough space for 5 adults and a few vehicles. Located just a little south of Portland, this was the perfect solution! I have to say, this property is a gem. The owners have done a fantastic job in appointing the home with everything needed for a comfortable stay. Kitchen was modern and well equipped for any cooking needs. The living spaces were well furnished and inviting, and all three of the bedrooms were a joy to stay in. Lets...
Five miles from the beach, newly remodeled home with lots of privacy.
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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.

Other property types in Chebeague Island

Exterior
2 duplex
3.0 star property
The price is SAR 945
SAR 1,405 total
includes taxes & fees
30 Jum. I - 31 Jum. I
2 duplex
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (75)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very Good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
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.

Recent reviews of Chebeague Island hotels
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