Holiday Rentals in Chebeague Island

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Holiday Rentals in Chebeague Island

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (82)
"Great spot, large space, cool design, clean, easy to walk all over town. "
The price is €238
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (64)
"The views from this house are amazing. It is literally steps away from the beach. We had a family gathering with all ages and everyone had a great time. The house is spacious, clean and comfortable. The owner was very responsive when we reached out. We were able to see fireworks from the balcony as we were there during the 4th. It is close enough to walk to the pier area for the arcade/rides and restaurants. We loved our time in this home and hope to return again!"
The price is €1,209
includes taxes & fees
10 Nov - 11 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave

Bright and airy condo with beachfront access and walkable entertainment nearby

7.6 out of 10, Good, (4)
"Ease of beach access. "
Bright and airy condo with beachfront access and walkable entertainment nearby

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (50)
"We loved everything about our stay here. Perfect location right on Old Orchard Beach. The house is perfect for what we needed/wanted. Wish we could have stayed longer. We would definitely come back for a longer stay next time we’re in Maine. "
The price is €435
includes taxes & fees
13 Oct - 14 Oct
Beach House ∆ Prime Location ∆ Steps to the Ocean

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very smooth and easy check-in. Very nice room and bathroom. Thank you so much for letting us stay! "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

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

10.0 out of 10, Exceptional, (230)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
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)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Captain's Guest Room w/private bath & house entrance. Walk to everything.

8.0 out of 10, Very good, (19)
"Dmitri is accommodating and check-in easy. Property details are accurate "
The price is €136
includes taxes & fees
2 Nov - 3 Nov
Captain's Guest Room w/private bath & house entrance. Walk to everything.

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
The price is €391
includes taxes & fees
10 Nov - 11 Nov
350 Yards to the beach. Pet friendly!

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
9.0 out of 10, Wonderful, (14)
"Very responsive host, even got us a pack and play for our youngest! Perfect house for a beach stay! Would stay again! "
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

2 min walk to the beach. Pet friendly condo

8.2 out of 10, Very good, (39)
"Host was very accommodating and easy to contact & communicate with. I'll definitely stay again! Highly recommended "
2 min walk to the beach. Pet friendly condo

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

9.8 out of 10, Exceptional, (64)
"Such a nice place for couples to stay. We really enjoyed our time. Highly recommend! "
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (53)
"The cottage location was beautiful, we had a wonderful time on the beach. The cottage could have been a little more clean than it was, but after letting the property owner know she addressed those issues. "
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

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

9.8 out of 10, Exceptional, (11)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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

9.8 out of 10, Exceptional, (220)
"The Property had everything we needed to relax and have a great time."
The price is €299
includes taxes & fees
7 Nov - 8 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Full sized home

9.8 out of 10, Exceptional, (45)
"Great location in Harpswell, close to several trails and restaurants. We stayed for about a month-the yard was fantastic and mowed weekly! We worked while we were here and had plenty of space to spread out-wifi was always fast/reliable and even when the power went out, the generator immediately kicked on! We did bring our senior dog and she loved laying on the deck. The ramp leading up to the back is very nice for older pups and people. "
The price is €301
includes taxes & fees
15 Oct - 16 Oct
Full sized home

Cozy Stay | Pool & Parking

4.0 out of 10, (2)
"Tiny rooms and unkempt property "
Cozy Stay | Pool & Parking

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (64)
"We stayed for a group trip to Portland and this was the perfect spot. Location is fantastic, lots of comfortable sleeping options, and great communication from the host. Highly recommend! "
The price is €949
includes taxes & fees
15 Oct - 16 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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, apart-hotels, 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 €136 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?

Captain's Guest Room w/private bath & house entrance. Walk to everything.: This holiday home rental outside of Chebeague Island comes with WiFi so that you can feel at home during your trip. Kitchen amenities include an electric kettle to make your meal-planning easier.

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.