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Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chebeague Island vacation rentals

Front of property

1. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NT$17,468
NT$23,845 total
includes taxes & fees
Aug 31 - Sep 1
Evalina Hotel
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (110 reviews)
"Really nice room and location"
United States
Victoria
The price is NT$10,236
NT$13,560 total
includes taxes & fees
Sep 1 - Sep 2
The Weldon Hotel
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

3. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is NT$10,871
NT$17,087 total
includes taxes & fees
Sep 7 - Sep 8
Fortland Island Campground
Apartment (2 Bedrooms) | Front of property

4. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is NT$4,036
NT$10,807 total
includes taxes & fees
Aug 26 - Aug 27
1/2 Mi to Pier: Wfh-friendly Apt in Maine!
House, 5 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, electric kettle

5. Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
3.5 star property
Gray
The price is NT$20,797
NT$43,881 total
includes taxes & fees
Sep 8 - Sep 9
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
Apartment (0 Bedroom) | Interior

6. Steps to Sandy Beach! Oceanfront Old Orchard Gem

Steps to Sandy Beach! Oceanfront Old Orchard Gem
3.0 star property
Old Orchard Beach
Steps to Sandy Beach! Oceanfront Old Orchard Gem
Apartment (0 Bedroom) | Front of property

7. 'beachfront 14' Condo on Old Orchard Beach

'beachfront 14' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NT$7,144
NT$11,844 total
includes taxes & fees
Sep 15 - Sep 16
'beachfront 14' Condo on Old Orchard Beach
Apartment (2 Bedrooms) | Interior

8. 1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach

1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach
3.0 star property
Old Orchard Beach
1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach
Apartment (2 Bedrooms) | Interior

9. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is NT$3,652
NT$10,388 total
includes taxes & fees
Aug 25 - Aug 26
Walk to Pier & Ocean: Apt in Old Orchard Beach!
Apartment (0 Bedroom) | Front of property

10. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NT$4,613
NT$9,086 total
includes taxes & fees
Sep 15 - Sep 16
'beachfront 9' Condo on Old Orchard Beach
Apartment (0 Bedroom) | Interior

11. 'beachfront 12' Condo on Old Orchard Beach

'beachfront 12' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
'beachfront 12' Condo on Old Orchard Beach
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

Best Western Merry Manor Inn

Best Western Merry Manor Inn

10/10 Excellent
"Awesome"
Michael 1-night trip
Posted 3 hours ago
Best Western Merry Manor Inn

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!

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.

How many vacation rentals are there in Chebeague Island?

Expedia has 5 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 Maine Narrow Gauge Railroad, or get out into nature at a spot like Winslow Memorial Park. 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.