Chebeague Island Holiday Rentals

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Holiday Rentals in Chebeague Island

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (65)
"Absolutely beautiful place to stay. "
The price is NZ$662
includes taxes & fees
20 July - 21 July
The Weldon Hotel

68 East Grand Ave

3.0 star property
8.0 out of 10, Very good, (4)
"nice place close to all"
68 East Grand Ave

Charming 3 bedroom lake house on Damariscotta Lake.

Charming 3 bedroom lake house on Damariscotta Lake.

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

Studio Unit Walkable Everywhere

The price is NZ$338
includes taxes & fees
13 July - 14 July
Studio Unit Walkable Everywhere

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (47)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is NZ$451
includes taxes & fees
13 July - 14 July
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (113)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views

2 bedroom cottage

9.6 out of 10, Exceptional, (4)
"quiet, clean, short walk to beach"
2 bedroom cottage

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (61)
"Beautiful location even in the offseason, gorgeous house with plenty of room for guests. Very close to Portland for a nice dinner and some drinks. We also went and played some golf at summit in OOB and had a blast. Outdoor grill was perfect and overall we had a great time! Excellent host excellent location and perfect for what we needed. Would recommend highly."
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

8.0 out of 10, Very good, (3)
"Loved how close it was to everything,could be a little more updated on a couple of things"
Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

7.4 out of 10, Good, (26)
"The cute apartment was clean with super comfy beds and very convenient to everything in OOB."
The price is NZ$1,027
includes taxes & fees
29 July - 30 July
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (82)
"Place was great "
Little Miss Cottages

Beach across the Street. Pets OK

8.8 out of 10, Excellent, (27)
"Perfect spot! Right near the beach and walking distance to all the best places. Very clean and chill little place perfect for what I was going for."
The price is NZ$557
includes taxes & fees
14 July - 15 July
Beach across the Street. Pets OK

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (12)
"Stunning property and great location! "
The price is NZ$1,438
includes taxes & fees
13 July - 14 July
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Beachfront Unit 17 | Right on Old Orchard Beach!

10.0 out of 10, Exceptional, (1)
"It was Amazing right next to the beach , def will be coming back !!"
Beachfront Unit 17 | Right on Old Orchard Beach!

Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

8.6 out of 10, Excellent, (55)
"Easy access and check in. The location was just what we wanted with it close to the beach."
The price is NZ$1,137
includes taxes & fees
27 July - 28 July
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Come enjoy 7 miles of beaches in sunny OOB in this 3 bedroom condo!

8.2 out of 10, Very good, (29)
"Good location and clean"
The price is NZ$1,553
includes taxes & fees
28 July - 29 July
Come enjoy 7 miles of beaches in sunny OOB in this 3 bedroom condo!

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (44)
"We had a wonderful stay the weekend after Christmas. The home had absolutely everything we needed and was both comfortable and beautiful! Everything was clearly labeled and so easy settle in. Very close to the beach which was awesome to visit even in the winter!"
The price is NZ$973
includes taxes & fees
20 July - 21 July
Beach House ∆ Prime Location ∆ Steps to 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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Frequently asked questions

Are there holiday rentals in Chebeague Island?

Yes, there are holiday rentals close to the most popular sights in Chebeague Island, or you can select a more secluded option if you're looking for a relaxing stay. Chebeague Island is known for its shopping and restaurants.

What are some of the best holiday rentals that Chebeague Island has to offer?

Charming 3 bedroom lake house on Damariscotta Lake.: This holiday home rental outside of Chebeague Island has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Chebeague Island?

Expedia has 3 holiday 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 Casco Bay. Wolfe's Neck Woods State Park and Bailey Island Bridge are a couple of places you'll find in the wider area.

What are holiday rentals like in Chebeague Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chebeague Island. Holiday rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.