Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

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Other types of properties in Bailey Island you may be interested in

La Quinta Inn & Suites by Wyndham Portland

2.5 star property
9.0 out of 10, Wonderful, (2027)
"I enjoyed my stay, room was quiet, slept well 4 nights!!! Only downside was skimpy breakfast compared to la quinta in Harrisburg earlier on our trip."
The price is S$123
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Portland

Casco Bay Hotel, Ascend Hotel Collection

3.5 star property
8.4 out of 10, Very good, (2375)
"Very good"
The price is S$105
includes taxes & fees
8 Dec - 9 Dec
Casco Bay Hotel, Ascend Hotel Collection

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1413)
"Great place but parking is a little high at $45 per night. "
The price is S$238
includes taxes & fees
1 Dec - 2 Dec
Portland Harbor Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Bailey Island?

Yes, there are holiday rentals in Bailey Island close to Land's End Gift Shop, or you can select a more secluded option if you're looking for a relaxing stay. Bailey Island is known for its shopping and seafood restaurants. Make sure you have time to check out the local tours and monuments during your trip.

How many holiday rentals are there in Bailey Island?

With 29 Expedia holiday rentals, you're guaranteed to find just the right place for your Bailey Island stay.

What can I see and do in Bailey Island?

Family-friendly attractions include Land's End Gift Shop, whereas Ragged Island is a spot to enjoy the outdoors. Bailey Island Bridge and Cobwork Bridge are other places to visit while you're in town.

What are holiday rentals like in Bailey Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bailey Island. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.