Chebeague Island Vacation Rentals

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Chebeague Island

The Weldon Hotel
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (80)
"Absolutely beautiful place to stay. "
The price is ￥52,609
￥68,505 total
includes taxes & fees
Oct 7 - Oct 8
The Weldon Hotel
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Outdoor dining

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (63)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
The price is ￥117,940
￥220,426 total
includes taxes & fees
Sep 28 - Sep 29
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
68 East Grand Ave
Luxury Condo | Private kitchen | Full-size fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

Bright and airy condo with beachfront access and walkable entertainment nearby

6.8 out of 10, (3)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby
Beach House ∆ Prime Location ∆ Steps to the Ocean
Beach nearby, sun loungers, beach towels

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (48)
"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 ￥22,814
￥74,181 total
includes taxes & fees
Oct 8 - Oct 9
Beach House ∆ Prime Location ∆ Steps to the Ocean
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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.
Cozy Coastal Condo with Parking – Walk to Beach & Town
Beach nearby

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.2 out of 10, Very Good, (14)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
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!
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (228)
"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
Grand Victorian on the Beach, Summer
Fridge, microwave, oven, stovetop

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (78)
"I would recommend this place to everyone. We had a great time."
Grand Victorian on the Beach, Summer
350 Yards to the beach. Pet friendly!
Beach

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!"
350 Yards to the beach. Pet friendly!
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

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

9.8 out of 10, Exceptional, (219)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
The price is ￥26,044
￥50,611 total
includes taxes & fees
Oct 25 - Oct 26
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Property grounds

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

8.2 out of 10, Very Good, (17)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is ￥11,310
￥22,061 total
includes taxes & fees
Oct 1 - Oct 2
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

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

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

2.0 star property
9.2 out of 10, Wonderful, (13)
"Host was very receptive and responsive while on the property. We had a great time. "
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
Gorgeous ocean-front home with stunning beach views
Full sized home
Terrace/patio

Full sized home

9.8 out of 10, Exceptional, (42)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is ￥29,522
￥53,900 total
includes taxes & fees
Oct 21 - Oct 22
Full sized home
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (140)
"We had a fantastic time. It was great being so close to the ocean. "
The price is ￥35,717
￥61,804 total
includes taxes & fees
Sep 28 - Sep 29
Oceanfront Condo! Spectacular Views From Private Large Balcony
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"This cozy cottage is in the beautiful town of Phippsburg, next to the break-taking beach of Popham State Park. With its site on the ocean shore, the sound of waves soothes your soul, and the beach lends all kinds of opportunities for exploring both at low tide and high tide. Our host and hostess were very responsive to our needs, and my daughter and I greatly enjoyed out stay."
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Terrace/patio

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (131)
"Right on the beach. Beautiful view. Clean and well appointed apartment Would definitely recommend and return "
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

10/10 Excellent
"Only thing that could have been improved was the $14 breakfast. We arrived at 8:30 am on a Wed & fruit & egg supplies needed to be replenished. I would also have preferred pastries rather than donuts. (I wouldn’t be mentioning this if the breakfast was included; paying for upgraded breakfast brought more expectations.)"
Betty 1-night trip
Posted 14 hours ago
Hyatt Place Portland Downtown - Old Port Square

Find out more about Chebeague Island

Find out more about Chebeague Island

Search for holiday rentals in Chebeague Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Chebeague Island using one of the methods below:

  • View our selection of featured holiday rentals in Chebeague Island
  • Use the map to find apartments and other holiday homes in the Chebeague Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chebeague Island while they last

Look no further and take a look at our great range of rental properties in Chebeague Island!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Chebeague Island is located on the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.