Chebeague Island Holiday Rentals

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Check prices for these dates

Tonight
10 Jul - 11 Jul
Tomorrow
11 Jul - 12 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Chebeague Island

The Weldon Hotel
Enjoy cooking in this kitchen with a sleek island, stainless steel appliances, and wooden cabinetry.

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (65)
"We had a wonderful stay. The room was super clean, spacious, cool and comfortable. The self check in process was easy and although there is no front desk, the staff was very responsive."
The price is HK$2,379
HK$3,181 total
includes taxes & fees
20 Jul - 21 Jul
The Weldon Hotel
68 East Grand Ave
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a marble countertop, and a sink.

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.
Living area

Charming 3 bedroom lake house on Damariscotta Lake.

Charming 3 bedroom lake house on Damariscotta Lake.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Kitchen area with microwave, toaster, refrigerator, and sink.

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 HK$1,356
HK$2,274 total
includes taxes & fees
13 Jul - 14 Jul
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Gorgeous ocean-front home with stunning beach views
Guests can enjoy a leisurely day on the beach with access to sun loungers and umbrellas.

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
Cozy living space with a kitchenette, sofa, dining table, and bench.

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
Experience a warm and inviting space with a high ceiling, exposed beams, and a comfortable bed.

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
Relax in a serene beachside setting with an outdoor seating area featuring a round table and comfortable chairs.

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
Beach

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.
Enjoy a game of volleyball on this expansive beach with a clear view of the ocean.

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 HK$3,132
HK$4,843 total
includes taxes & fees
29 Jul - 30 Jul
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Little Miss Cottages
Relax in a serene outdoor space with Adirondack chairs, a picnic table, and a fire pit.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (82)
"Place was great "
Little Miss Cottages
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Enjoy the ocean view from this spacious balcony with a table and two chairs.

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 HK$4,204
HK$6,781 total
includes taxes & fees
13 Jul - 14 Jul
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Smart TV

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 2 bedroom condo.
Enjoy a tranquil beach experience with a volleyball net set up for recreational activities.

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 HK$3,525
HK$5,365 total
includes taxes & fees
27 Jul - 28 Jul
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Relax on the deck with a view of the calm lake, featuring comfortable seating and a barbecue grill.

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (84)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Oceanfront Condo! Spectacular Views From Private Large Balcony
Enjoy a peaceful beach experience with a pier stretching into the calm sea.

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (130)
"Great place. Perfect location if you want to be in the middle of it all."
The price is HK$3,532
HK$5,331 total
includes taxes & fees
13 Jul - 14 Jul
Oceanfront Condo! Spectacular Views From Private Large Balcony
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Enjoy the serene forest views from this deck with a bench and table.

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Seaside Studio | Accommodates 4| Parking Available
Stroll along the pier and enjoy the serene views of the calm water.

Seaside Studio | Accommodates 4| Parking Available

2.0 star property
7.4 out of 10, Good, (3)
"We had a wonderful stay. The unit was immaculate and comfortable. The beach was steps away. Definitely recommend a stay!"
Seaside Studio | Accommodates 4| Parking Available
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Fridge, microwave, oven, stovetop

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"Cute cabin in small quiet campground close to pool and short walk to downtown. The cabin itself was clean, cozy, and had everything we needed for a comfortable stay. Perfect for a small family getaway or a relaxing weekend."
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Your own private island! Rustic and close to Nature.
Situated lakeside, this serene retreat offers a peaceful escape with a lighthouse nearby.

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (32)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.
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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This holiday home rental outside of Chebeague Island offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Land's End Gift Shop, 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.