Chebeague Island Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Chebeague Island

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (85)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$263 nightly
The price is $280
Nov 4 - Nov 5
Total with taxes and fees
The Weldon Hotel
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. "
United States
Benjamin
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. "
United States
TAMMY K.
Bright and airy condo with beachfront access and walkable entertainment nearby
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
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
2.0 star property
10.0 out of 10, Exceptional, (5)
"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. "
United States
Tamerra J.
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
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!"
Canada
Sebastien M.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
350 Yards to the beach. Pet friendly!
8.0 out of 10, Very Good, (34)
"Bring your own linen if you plan on using pull out couch. Also it’s not a 2 bedroom but a 1 bedroom with full size pullout couch in sitting area which is good for kids only. You have to go through private bedroom to access bathroom. Only 1 Ac in the unit located in the private bedroom so if you close the door to the bedroom the sitting area does not get AC. "
United States
Jonnie Rose C.
$401 nightly
The price is $437
Nov 1 - Nov 2
Total with taxes and fees
350 Yards to the beach. Pet friendly!
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (55)
"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. "
United States
Chanmaly V.
$443 nightly
The price is $483
Nov 2 - Nov 3
Total with taxes and fees
Beach House ∆ Prime Location ∆ Steps to the Ocean
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
9.6 out of 10, Exceptional, (66)
"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!"
United States
Jessica S.
$1,141 nightly
The price is $1,244
Nov 2 - Nov 3
Total with taxes and fees
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)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
United States
Elizabeth h.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
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. "
United States
Hannah K.
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
2 min walk to the beach. Pet friendly condo
8.2 out of 10, Very Good, (41)
"Host was very accommodating and easy to contact & communicate with. I'll definitely stay again! Highly recommended "
United States
Grace
2 min walk to the beach. Pet friendly condo
Studio Unit Walkable Everywhere
5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
$133 nightly
The price is $135
Oct 29 - Oct 30
Total with taxes and fees
Studio Unit Walkable Everywhere
Little Miss Cottages - Two Bedroom Cottage
9.4 out of 10, Exceptional, (3)
"Excellent place, so much fun!!!"
United States
Gregory D.
$257 nightly
The price is $281
Oct 29 - Oct 30
Total with taxes and fees
Little Miss Cottages - Two Bedroom Cottage
Cozy Stay | Pool & Parking
4.0 out of 10, (2)
"Tiny rooms and unkempt property "
United States
Christina B.
Cozy Stay | Pool & Parking
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
2.0 star property
9.2 out of 10, Wonderful, (15)
"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
Gorgeous ocean-front home with stunning beach views
9.4 out of 10, Exceptional, (123)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
United States
Victoria H.
Gorgeous ocean-front home with stunning beach views
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (222)
"Perfect little get away! "
United States
Anonymous traveler
$310 nightly
The price is $338
Oct 29 - Oct 30
Total with taxes and fees
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
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
Cozy Motel Stay – 2 Full Beds, Pool & Free Parking
8.0 out of 10, Very Good, (2)
"The description is inaccurate. It is run down and in an unsafe area. The check-in instructions repeatedly said to close your door immediately behind you and lock it. As soon as we pulled up it was clear why. I was traveling alone with my 16 year old daughter for a mother daughter’s trip. Needless to say there was no way I felt comfortable staying at the property alone with her. We ended up getting a nice safe room at the Ramada about 5 miles away. Be very wary of this place! There is a reason...
United States
Nina K.
Cozy Motel Stay – 2 Full Beds, Pool & Free Parking
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chebeague Island Hotel Reviews

Find out more about Chebeague Island

Everything you need to know about Chebeague Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chebeague Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chebeague Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chebeague Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chebeague Island rentals

At Expedia, we put the best Chebeague Island vacation 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 vacation.

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 vacation rentals in Chebeague Island?

Yes, we have vacation rentals near popular attractions in Chebeague Island, or you can select a secluded option if you're looking for relaxation. Chebeague Island is known for its shopping and restaurants.

What's the top vacation rental in Chebeague Island?

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

How many vacation rentals are there in Chebeague Island?

Expedia has 3 vacation 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 larger area.

What are vacation rentals like in Chebeague Island?

Vacation rentals are private properties you can book for several days or more in Chebeague Island. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a small group gathering.