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, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is NZ$487
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel
68 East Grand Ave
3.0 star property
8.6 out of 10, Excellent, (9)
"Across from the beach, close to a lot of activities, the space is up to date and very comfortable , decorated nicely. Outdoor porch area was a nice addition to having extra space. The train does go by very early in the am but that’s not just for this space on the avenue but is something to consider if that bothers you. Communication with Nichole was very easy and she was great to deal with! We loved to space and will definitely stay here again! "
United States
Jeffrey
68 East Grand Ave
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
9.6 out of 10, Exceptional, (66)
"Made a great place for a business retreat. WiFi worked well and we had plenty of space to spread out."
United States
dan b.
The price is NZ$2,195
includes taxes & fees
9 Nov - 10 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
9.8 out of 10, Exceptional, (11)
"This place is so cute, so convenient and so fun. The stained glass and custom woodwork everywhere are wonderful. Owner is so kind and helpful"
United States
Caitlin M.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
2 min walk to the beach. Pet friendly condo
8.2 out of 10, Very good, (41)
"Over all it was good, bathroom was off bedroom, not convenient for other guest staying on futon in living room. Backyard for dogs was very small, but enough space for the pups to do their duty. In all it worked for the few days we were there!"
United States
Cindy H.
2 min walk to the beach. Pet friendly condo
Cozy Stay | Pool & Parking
4.0 out of 10, (2)
"Tiny rooms and unkempt property "
United States
Christina B.
Cozy Stay | Pool & Parking
Studio Unit Walkable Everywhere
5.8 out of 10, (6)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
United States
Anonymous traveller
The price is NZ$247
includes taxes & fees
7 Nov - 8 Nov
Studio Unit Walkable Everywhere
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (223)
"Great location."
United States
donna S.
The price is NZ$598
includes taxes & fees
7 Nov - 8 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Captain's Guest Room w/private bath. Walk to everything.
8.2 out of 10, Very good, (21)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
United States
Benjamin E.
The price is NZ$283
includes taxes & fees
9 Nov - 10 Nov
Captain's Guest Room w/private bath. Walk to everything.
In-town no frills 2 bedroom apt
8.4 out of 10, Very good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is NZ$266
includes taxes & fees
9 Nov - 10 Nov
In-town no frills 2 bedroom apt
Little Miss Cottages - Two Bedroom Cottage
9.4 out of 10, Exceptional, (3)
"Cute little cottage. The floor in one bedroom has a real slant to it."
United States
Paula F.
The price is NZ$524
includes taxes & fees
10 Nov - 11 Nov
Little Miss Cottages - Two Bedroom Cottage
The Dollhouse
9.2 out of 10, Wonderful, (5)
"We had a great time! The place was exactly like the pictures. It was clean and had lots of amenities. My only suggestion would have more towels because we had five people and four bath towels. "
United States
Molly D.
The price is NZ$1,320
includes taxes & fees
7 Nov - 8 Nov
The Dollhouse
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
9.8 out of 10, Exceptional, (64)
"My wife and I both enjoyed our stay and found the unit to be very cute, clean and comfortable. The owners were also quite nice and communicated very well whenever we reached out to them. We had a great stay!"
United States
Russell R.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
9.8 out of 10, Exceptional, (44)
"Great house with lots of room for a big family. So close to the beach with great views. Great outdoor spaces as well! "
United States
Moria B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (164)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Updated Long Island Maine Cottage
10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Private Entrance Residential Portland
9.2 out of 10, Wonderful, (5)
"Check in was simple. Quaint place. "
United States
Danielle C.
Private Entrance Residential Portland
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
2.0 star property
9.0 out of 10, Wonderful, (16)
"Very responsive host, even got us a pack and play for our youngest! Perfect house for a beach stay! Would stay again! "
United States
Matthew D.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
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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Top Chebeague Island Hotel Reviews

Find out more about Chebeague Island

Everything you need to know about Chebeague Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chebeague Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chebeague Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chebeague Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chebeague Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chebeague Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chebeague Island holiday rentals we have selected for you start as low as NZ$247 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chebeague Island rentals

At Expedia, we put the best Chebeague Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chebeague Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chebeague Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chebeague Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Chebeague Island is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.