Chebeague Island Vacation Rentals

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Tonight
Nov 10 - Nov 11
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Nov 11 - Nov 12
This weekend
Nov 14 - Nov 16
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Nov 21 - Nov 23

Vacation Rentals in Chebeague Island

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

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is ￥28,306
￥42,361 total
includes taxes & fees
Dec 7 - Dec 8
The Weldon Hotel
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

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

Bailey Island
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
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Outdoor dining
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"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 ￥91,899
￥190,807 total
includes taxes & fees
Nov 16 - Nov 17
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Beach nearby
2 min walk to the beach. Pet friendly condo

2 min walk to the beach. Pet friendly condo

Old Orchard Beach
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
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

Old Orchard Beach
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
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 traveler
The price is ￥10,471
￥21,487 total
includes taxes & fees
Nov 12 - Nov 13
Studio Unit Walkable Everywhere
Beach
Little Miss Cottages - Two Bedroom Cottage

Little Miss Cottages - Two Bedroom Cottage

Old Orchard Beach
9.0 out of 10, Wonderful, (4)
"Cute little cottage. The floor in one bedroom has a real slant to it."
United States
Paula F.
The price is ￥21,540
￥45,721 total
includes taxes & fees
Nov 30 - Dec 1
Little Miss Cottages - Two Bedroom Cottage
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

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

Old Orchard Beach
9.8 out of 10, Exceptional, (224)
"The view off the deck was breathtaking "
United States
Raymond
The price is ￥26,849
￥52,677 total
includes taxes & fees
Nov 13 - Nov 14
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Fridge, microwave, oven, stovetop
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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

Old Orchard 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
Property grounds
Captain's Guest Room w/private bath. Walk to everything.

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

Bath
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 ￥8,745
￥24,583 total
includes taxes & fees
Nov 12 - Nov 13
Captain's Guest Room w/private bath. Walk to everything.
2 bedrooms, WiFi, bed sheets
The Dollhouse

The Dollhouse

Old Orchard Beach
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 ￥69,039
￥113,715 total
includes taxes & fees
Nov 12 - Nov 13
The Dollhouse
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
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 ￥12,082
￥23,098 total
includes taxes & fees
Nov 12 - Nov 13
In-town no frills 2 bedroom apt
On the beach, sun loungers
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Old Orchard Beach
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
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Updated Long Island Maine Cottage

Long Island
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
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Private Entrance Residential Portland

Deering Center
9.2 out of 10, Wonderful, (5)
"Check in was simple. Quaint place. "
United States
Danielle C.
Private Entrance Residential Portland
Beach nearby
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Old Orchard Beach
9.8 out of 10, Exceptional, (97)
"This was the second year that we’ve stayed here. The house is beautiful and we had an amazing time."
United States
jill s.
The price is ￥76,557
￥171,743 total
includes taxes & fees
Dec 3 - Dec 4
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
Private kitchen
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

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

2.0 star property
Grand Beach
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
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (166)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Interior
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Old Orchard Beach
10.0 out of 10, Exceptional, (32)
"Great location and great host. "
United States
Dwight P.
The price is ￥30,531
￥68,229 total
includes taxes & fees
Nov 13 - Nov 14
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Very clean hotel"
Marijana 2-night trip
Posted 2 days ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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

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.