A rocky shoreline with a boat, a house, and a forest in the background.

Bailey Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Bailey Island vacation rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (115 reviews)
"Really nice room and location"
United States
Victoria
The price is NT$11,159
NT$14,540 total
includes taxes & fees
Sep 7 - Sep 8
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NT$17,285
NT$23,595 total
includes taxes & fees
Aug 30 - Aug 31
Evalina Hotel
A spacious living room with large windows, a sofa, a chair, and a small table.

3. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is NT$3,225
NT$8,575 total
includes taxes & fees
Sep 23 - Sep 24
1 Mi to Maine Street! Mcm-style Home in Brunswick
A yurt with a bed, a desk, and a view of the outdoors.

4. 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$8,771
NT$14,730 total
includes taxes & fees
Sep 7 - Sep 8
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bailey Island Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"Clean rooms. I liked having no carpet!"
Danielle 1-night trip
Posted 1 hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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.

How many vacation rentals are there in Bailey Island?

With 32 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.