Bailey Island Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Bailey Island

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

Portland Harbor Hotel
Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, 1,196 reviews
"Nice building in a pleasant neighborhood. Comfortable bed. Convenient coffee maker. Helpful valet parking. "
The price is S$399
per night
9 Jun - 10 Jun
Portland Harbor Hotel
Casco Bay Hotel, Ascend Hotel Collection
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, 1,530 reviews
"Easy check in an out, friendly staff, free parking which is a plus, close to airport and central to a lot of restaurants and shopping. Bed was nice and comfortable. "
The price is S$124
per night
2 Jun - 3 Jun
Casco Bay Hotel, Ascend Hotel Collection
Canopy by Hilton Portland Waterfront
Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, 656 reviews
"Super comfortable, great amenities and customer service. Highly recommend. "
The price is S$446
per night
2 Jun - 3 Jun
Canopy by Hilton Portland Waterfront
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.

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.

Recent reviews of Bailey Island properties
Expedia verified reviews

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

5/5 Excellent
"It was mine and my husband’s 25th Wedding Anniversary. The staff wished us a happy anniversary upon arrival and even gave us an upgrade to a very scenic room. We over looked the terrace and had a great view of the water. The room was very nice and spacious. We were walking distance to every thing. The attached parking garage is really nice well. We would definitely stay here again. Very friendly staff as well. "
A verified traveller stayed at Cambria Hotel Portland Downtown-Old Port
Posted 20 hours ago
Cambria Hotel Portland Downtown-Old Port