Bailey Island Holiday Rentals

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Check prices for these dates

Tonight
15 Nov - 16 Nov
Tomorrow
16 Nov - 17 Nov
Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov

Holiday Rentals in Bailey Island

On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Living area
The Weldon Hotel

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (87)
"Absolutely beautiful place to stay. "
United States
James
The price is HK$1,434
HK$2,146 total
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
United States
Anonymous traveller
The price is HK$531
HK$1,089 total
includes taxes & fees
17 Nov - 18 Nov
Studio Unit Walkable Everywhere
Property grounds
Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath
8.2 out of 10, Very good, (21)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
United States
Benjamin E.
The price is HK$665
HK$894 total
includes taxes & fees
17 Nov - 18 Nov
Captain's Guest Room w/private bath. Walk to everything.
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Updated Long Island Maine Cottage

Long Island
10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Private Entrance Residential Portland

Deering Center
9.2 out of 10, Wonderful, (5)
"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.
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (167)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very good, (15)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is HK$612
HK$1,170 total
includes taxes & fees
17 Nov - 18 Nov
In-town no frills 2 bedroom apt
Property grounds
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Falmouth
8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Exterior
Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell
9.4 out of 10, Exceptional, (23)
"Really well received with good A/C and a lovely view on the water. It was more spacious than anticipated and has all the kitchen and home tools for the stay. Really recommended!"
Canada
Hugo L.
Beautiful Oceanfront House- Stunning Water Views
Exterior detail
Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Munjoy Hill
10.0 out of 10, Exceptional, (62)
"Cozy, clean and quiet, within short walking distance to restaurants, coffee shops, breweries, distilleries and shopping. "
United States
Jane
Sunny Modern Oasis in Portland’s Trendy East End
Exterior
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Downtown Portland
9.8 out of 10, Exceptional, (20)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
The price is HK$1,159
HK$3,093 total
includes taxes & fees
19 Nov - 20 Nov
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Outdoor dining
Knock on Wood | Airy Charm in Heart of Downtown

Knock on Wood | Airy Charm in Heart of Downtown

Parkside
8.8 out of 10, Excellent, (25)
"stayed for one night to celebrate prom, it was a great central location, parking was a bit difficult to find though. Also the sheets were wet, not sure if the humidifier was broken. Overall good stay! would book again"
United States
Sabrina C.
The price is HK$1,075
HK$2,535 total
includes taxes & fees
9 Dec - 10 Dec
Knock on Wood | Airy Charm in Heart of Downtown
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (13)
"The place is amazing with lots of room for a family, and great views of the water from almost everywhere. The neighborhood is quiet and the people were very friendly. "
United States
Joseph V.
The price is HK$979
HK$2,091 total
includes taxes & fees
30 Nov - 1 Dec
Fantastic Waterfront Views
Terrace/patio
Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island
9.8 out of 10, Exceptional, (36)
"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"
United States
Abby P.
Large, light filled 4 bedroom house - walk to ocean and ferry
Fridge, microwave, oven, stovetop
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Boothbay Harbor
9.2 out of 10, Wonderful, (100)
"This home is situated on a quiet street, but within a half-mile walking distance to the shops, restaurants, and puffin cruise piers. The house is comfortable and well-equipped, with several nice extras. The house was very clean when we arrived. The location is perfect, and we enjoyed sitting outside by the cove."
United States
Debbie A.
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Interior
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)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
United States
Kirsten
The price is HK$972
HK$1,788 total
includes taxes & fees
17 Nov - 18 Nov
Charming Studio apartment with WiFi, AC in welcoming Portland
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful, single story ranch. Next to city park with ocean view!

Beautiful, single story ranch. Next to city park with ocean view!

Back Cove
9.2 out of 10, Wonderful, (19)
"We had a wonderful stay with friends! Ken was very accommodating to all of our needs!"
United States
Ryan D.
Beautiful, single story ranch. Next to city park with ocean view!
Interior
Popham Beach Direct Oceanfront Cottage Steps to the sand

Popham Beach Direct Oceanfront Cottage Steps to the sand

Phippsburg
9.8 out of 10, Exceptional, (69)
"We enjoyed our stay and would heartily recommend this wonderful cottage to everyone!"
United States
David G.
Popham Beach Direct Oceanfront Cottage Steps to the sand
Terrace/patio
Back yard paradise

Back yard paradise

Portland
9.8 out of 10, Exceptional, (22)
"I live in California, but my son was married in Portland (our home state). We spent a long weekend close to family and wedding activities. This is a comfortable home, in a great location. I feel fortunate to have chosen the perfect VRBO."
United States
Tracey C.
Back yard paradise
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Yes"
LeeAnne 1-night trip
Posted 1 day ago
Hampton Inn Portland Downtown - Waterfront

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 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?

New 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 22 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.