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Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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 P33,508
P45,741 total
includes taxes & fees
Aug 31 - Sep 1
Evalina Hotel
Private kitchen

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 P19,636
P26,012 total
includes taxes & fees
Sep 1 - Sep 2
The Weldon Hotel
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 P20,853
P32,777 total
includes taxes & fees
Sep 7 - Sep 8
Fortland Island Campground
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 P7,743
P20,730 total
includes taxes & fees
Aug 26 - Aug 27
1/2 Mi to Pier: Wfh-friendly Apt in Maine!
Private kitchen

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 P39,893
P84,174 total
includes taxes & fees
Sep 8 - Sep 9
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
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
The price is P12,904
P22,669 total
includes taxes & fees
Aug 24 - Aug 25
Steps to Sandy Beach! Oceanfront Old Orchard Gem
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 P13,703
P22,720 total
includes taxes & fees
Aug 23 - Aug 24
'beachfront 14' Condo on Old Orchard Beach
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
The price is P8,849
P21,935 total
includes taxes & fees
Aug 19 - Aug 20
1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach
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 P7,005
P19,926 total
includes taxes & fees
Aug 25 - Aug 26
Walk to Pier & Ocean: Apt in Old Orchard Beach!
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 P8,849
P17,429 total
includes taxes & fees
Sep 14 - Sep 15
'beachfront 9' Condo on Old Orchard Beach
Interior

11. 'beachfront 12' Condo on Old Orchard Beach

'beachfront 12' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is P15,178
P24,328 total
includes taxes & fees
Sep 8 - Sep 9
'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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"John at front desk went above and beyond for us. The free shuttle is a major plus. I wish the restaurant had been open but it was closed the days we were there"
Pastor Doug 1-night trip
Posted 1 hour ago
Clarion Hotel Portland Airport ME

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.