Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Bailey Island vacation rentals

Luxury Penthouse, 2 Bedrooms, Partial Ocean View | Living room

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (3 reviews)
"Spacious, clean, and in the perfect location in Old Port."
United States
Celine
The price is ￥81,471
￥112,839 total
includes taxes & fees
Jun 16 - Jun 17
Evalina Hotel
Deluxe Suite, 1 King Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (101 reviews)
"Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"
United States
Roberta
The price is ￥54,720
￥71,663 total
includes taxes & fees
Jul 6 - Jul 7
The Weldon Hotel
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

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 ￥60,659
￥66,118 total
includes taxes & fees
Jun 18 - Jun 19
Fortland Island Campground
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 Bailey Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The check-in was so easy and the staff was so friendly and helpful. They gave us recommendations for food and sights. The location was perfect for both the old port and the art district. The room was beautiful and welcoming but was even better was the beautiful view of the bay. We loved waking up to the beautiful view. Parking was easy and the hotel was comfortable."
Francis 3-night trip
Posted 1 hour ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Bailey Island

Search for holiday rentals in Bailey Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Bailey Island using one of the methods below:

  • View our selection of featured holiday rentals in Bailey Island
  • Use the map to find apartments and other holiday homes in the Bailey Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bailey Island while they last

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

Frequently asked questions

Can I find a vacation rental in Bailey Island?

Yes, we give you a choice of vacation rentals in Bailey Island near Land's End Gift Shop, or you can choose a secluded option if you're looking for extra privacy while you relax. 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.

What are some of the best vacation rentals that Bailey Island has to offer?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated vacation home rental in Bailey 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 Bailey Island?

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

What can I see and do in Bailey Island?

Mackerel Cove and Ragged Island are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Land's End Gift Shop. Bailey Island Bridge and Cobwork Bridge are other places to visit while you're in town.

What are vacation rentals like in Bailey Island?

Vacation rentals are private properties you can reserve for several days or longer in Bailey Island. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean 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 have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.