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Our top choices for Bailey Island holiday rentals

Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.0 out of 10, Very good, (4 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is £229
includes taxes & fees
10 Jun - 11 Jun
Sunset Hideaway on Bailey Island

Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Captain's Guest Room. The authenticity & value in one place. Walk to everything!
Bath
8.2 out of 10, Very good, (21 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is £107
includes taxes & fees
1 Jun - 2 Jun
Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (9 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is £166
includes taxes & fees
1 Jun - 2 Jun
Modern style in historic building in downtown Bath

Captain's House 1BR Apt. Walk to everything.

Captain's House 1BR Apt. Walk to everything.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is £111
includes taxes & fees
7 Jun - 8 Jun
Captain's House 1BR Apt. Walk to everything.

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (150 reviews)
"Such a fabulous stay. The space was bright, clean, and comfortable, and the special touches made it feel even more welcoming. It was larger than expected, and we loved having a mini fridge and coffee machine, perfect for slow mornings or a little wine and cheese at the end of the day. We’d return in a heartbeat."
Canada
Coral
The price is £115
includes taxes & fees
9 Jun - 10 Jun
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is £174
includes taxes & fees
28 May - 29 May
Sunny Spot with Private Parking.

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful new boutique hotel in Portland! Easy access to the Old Port and everything Portland has to offer. Very quiet, clean and well appointed rooms. The kitchen makes all the difference, even for a short stay! We loved our visit so much that we've booked a second trip!"
United States
Allison
The price is £407
includes taxes & fees
1 Jun - 2 Jun
Evalina Hotel

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is £241
includes taxes & fees
31 May - 1 Jun
Modern, Luxurious Cabin in the Woods - 03

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is £272
includes taxes & fees
29 May - 30 May
Camp Forever cottage

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is £368
includes taxes & fees
28 May - 29 May
•Peaceful Private Freeport 2 BR Home on the Ocean•

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is £134
includes taxes & fees
9 Jun - 10 Jun
Private Entrance Residential Portland

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is £185
includes taxes & fees
28 May - 29 May
Peaceful & minutes from the Old Port with private parking

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is £284
includes taxes & fees
31 May - 1 Jun
Large, luxurious geodesic dome - 04

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is £238
includes taxes & fees
3 Jun - 4 Jun
Fantastic Waterfront Views

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is £205
includes taxes & fees
2 Jun - 3 Jun
2 bedroom w/ expansive water views

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.4 out of 10, Exceptional, (100 reviews)
"Great location with easy parking"
United States
Lauren J.
The price is £196
includes taxes & fees
4 Jun - 5 Jun
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is £208
includes taxes & fees
9 Jun - 10 Jun
Charming 1-bedroom ADU in wonderful Portland neighborhood

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is £182
includes taxes & fees
3 Jun - 4 Jun
Mid Coast Getaway w/ water views

Luxury on Back Cove - Three Gables

Luxury on Back Cove - Three Gables
Rosemont
10.0 out of 10, Exceptional, (9 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is £337
includes taxes & fees
28 May - 29 May
Luxury on Back Cove - Three Gables

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is £186
includes taxes & fees
15 Jun - 16 Jun
Charming Studio apartment with WiFi, AC in welcoming Portland
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

Find out more about Bailey Island

Everything you need to know about Bailey Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bailey Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bailey Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Bailey Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bailey Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bailey Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bailey Island holiday rentals we have selected for you start as low as £107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bailey Island rentals

At Expedia, we put the best Bailey Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bailey Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bailey Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bailey Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated holiday home rental in Bailey Island is located on the beach, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Bailey Island?

With 30 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?

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 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.