Vacation rentals on Bailey Island - HomeToGo base64Hash Vacation rentals on Bailey Island - HomeToGo

Vacation rentals on Bailey Island

Browse 116 available vacation homes and compared across 2 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Farmhouse
    • Apartment

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • WiFi
    • TV
    • Kitchen
    • Washing machine
    • Balcony/patio
    • Parking
    • Air conditioning
    • Fireplace
    • Microwave
    • Pool
    • Dishwasher
    • Yard
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals on Bailey Island

Discover your ideal Bailey Island vacation rental with real-time comparisons of 116 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Bailey Island
House ∙ 14 guests ∙ 6 bedrooms

Vacation home with grill & terrace

Bailey Island, Harpswell, Maine, United States
This Harpswell house rental features a fireplace, kitchen, and balcony, perfect for gatherings of up to 14 guests.
from $480
per night
Excellent(46 ratings)
from $480
per night
View deal
House Bailey Island
House ∙ 13 guests ∙ 4 bedrooms

Family-friendly nice vacation home with patio & barbeque | Pets are welcome

Bailey Island, Harpswell, Maine, United States
This Harpswell house rental features beach access, a fireplace, and accommodations for 13, perfect for a family getaway.
from $163
per night
Outstanding(50 ratings)
from $163
per night
View deal
House Bailey Island
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped beautiful house with garden, barbeque & terrace | City view | Close to the beach

Bailey Island, Harpswell, Maine, United States
This house rental on Bailey Island offers beach access, a yard, and a balcony, perfect for families or groups of up to 10.
from $871
per night
Outstanding(171 ratings)
from $871
per night
View deal
House Bailey Island
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly house with BBQ & yard | Pets allowed

Bailey Island, Harpswell, Maine, United States
This Harpswell house rental features a yard, balcony, and fireplace, perfect for families and pets seeking a memorable getaway.
from $197
per night
Outstanding(112 ratings)
from $197
per night
View deal
Cabin Bailey Island
Cabin ∙ 3 guests ∙ 2 bedrooms

Family-friendly nice cottage with yard & patio

Bailey Island, Harpswell, Maine, United States
This cozy cabin in Harpswell features a kitchen, yard, and parking, perfect for a family getaway with room for three.
from $174
per night
Outstanding(34 ratings)
from $174
per night
View deal
House Bailey Island
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly house with garden, BBQ & patio

Bailey Island, Harpswell, Maine, United States
This waterfront house rental on Bailey Island features a kitchen, yard, and beach access, perfect for families and groups of six.
from $357
per night
Outstanding(270 ratings)
from $357
per night
View deal
House Bailey Island
House ∙ 2 guests ∙ 2 bedrooms

House with barbecue

Bailey Island, Harpswell, Maine, United States
This house rental on Orr's Island features a kitchen, family-friendly setup, and parking for a perfect getaway for two.
from $214
per night
Outstanding(10 ratings)
from $214
per night
View deal
House Bailey Island
House ∙ 11 guests ∙ 5 bedrooms

Vacation home with garden, terrace & grill | Nature view

Bailey Island, Harpswell, Maine, United States
This house rental on Orr's Island features a yard, fireplace, and kitchen, welcoming up to 11 guests and their pets.
from $376
per night
Outstanding(200 ratings)
from $376
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 1 bedroom

Child-friendly pleasant cottage with grill, patio & yard | Good for workation | Pet-friendly

Bailey Island, Harpswell, Maine, United States
This Harpswell cabin offers a fireplace, kitchen, and yard, perfect for families and pets, accommodating up to four guests.
from $192
per night
Outstanding(173 ratings)
from $192
per night
View deal
Cabin Bailey Island
Cabin ∙ 2 guests ∙ 1 bedroom

Beautiful cabin with BBQ & patio | Next to the beach | Pets allowed

Bailey Island, Harpswell, Maine, United States
This waterfront cabin on Orr's Island offers a kitchen, parking, and pet-friendly space for a perfect getaway for two.
from $134
per night
Outstanding(33 ratings)
from $134
per night
View deal
Cabin Bailey Island
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbeque, yard & patio

Bailey Island, Harpswell, Maine, United States
This Harpswell cabin features a kitchen, fireplace, and yard, making it ideal for families and pets seeking a memorable getaway.
from $143
per night
Outstanding(43 ratings)
from $143
per night
View deal
House Bailey Island
House ∙ 6 guests ∙ 2 bedrooms

Child-friendly nice vacation home with BBQ & terrace

Bailey Island, Harpswell, Maine, United States
This house rental on Bailey Island features a fireplace, kitchen, balcony, and parking, perfect for a getaway with friends or family.
from $299
per night
Outstanding(22 ratings)
from $299
per night
View deal
Apartment Bailey Island
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with patio & BBQ | Nature view | Next to the beach

Bailey Island, Harpswell, Maine, United States
This cozy apartment on Bailey Island features a kitchen and parking, perfect for a romantic getaway by the sea.
from $392
per night
Outstanding(28 ratings)
from $392
per night
View deal
House Bailey Island
House ∙ 7 guests ∙ 4 bedrooms

Children-friendly house with yard, patio & barbeque | Suitable for remote work

Bailey Island, Harpswell, Maine, United States
This house rental on Orr's Island features a fireplace, kitchen, yard, and parking, perfect for family gatherings of up to 7.
from $249
per night
Excellent(22 ratings)
from $249
per night
View deal
Cabin Bailey Island
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with patio & barbeque | Nature view

Bailey Island, Harpswell, Maine, United States
This cozy cabin in Harpswell features a kitchen and parking, making it the perfect retreat for a romantic getaway for two.
from $137
per night
Outstanding(54 ratings)
from $137
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin Bailey Island
from $423
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with patio, grill & yard | Nature view

4.9
Outstanding(42 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
House Bailey Island
from $205
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden, barbeque & patio | Nature view

5.0
Outstanding(44 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
Condo Bailey Island
from $395
per night
Condo ∙ 4 guests ∙ 1 bedroom

Nice condo with BBQ & patio | Nature view

5.0
Outstanding(36 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

Cabin Bailey Island
from $214
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with barbecue & patio | Nature view

4.9
Outstanding(17 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony/Patio
View deal
Cabin Bailey Island
from $426
per night
Cabin ∙ 7 guests ∙ 4 bedrooms

Cottage with terrace, grill & yard

5.0
Outstanding(36 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony/Patio
View deal
Cabin Bailey Island
from $527
per night
Cabin ∙ 10 guests ∙ 6 bedrooms

Family-friendly beautiful cottage with grill & pool | Nature view | Pet-friendly

5.0
Outstanding(10 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

Cabin Bailey Island
from $260
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with patio & barbeque | Close to the beach

4.7
Excellent(22 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony
View deal
House Bailey Island
from $592
per night
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque & terrace

Bailey Island, Harpswell, Maine, United States
Balcony
View deal
House Bailey Island
from $331
per night
House ∙ 6 guests ∙ 2 bedrooms

House with yard, barbecue & terrace | Nature view

4.9
Outstanding(68 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals on Bailey Island offering exceptional value for money

Cabin Bailey Island
from $298
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with barbeque & terrace | Nature view

4.7
Excellent(24 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
Cabin Bailey Island
from $522
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Family-oriented cottage with patio, garden & BBQ | Nature view | Next to the beach | Good for workation

4.8
Outstanding(72 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
House Bailey Island
from $255
per night
House ∙ 4 guests ∙ 4 bedrooms

Vacation home | Nature view | Next to the beach

5.0
Outstanding(47 ratings)
Bailey Island, Harpswell, Maine, United States
View deal

Top-Rated Vacation rentals on Bailey Island

Book the highest-rated Bailey Island vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Cabin Bailey Island
from $628
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with terrace, barbeque & garden | Nature view

5.0
Outstanding(65 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
Cabin Bailey Island
from $443
per night
Cabin ∙ 14 guests ∙ 5 bedrooms

Family-oriented cottage with garden, barbecue & terrace | Nature view | Suitable for remote work | Pets are welcome

5.0
Outstanding(39 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
Cabin Bailey Island
from $208
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with grill, garden & terrace | Nature view

4.8
Outstanding(33 ratings)
Bailey Island, Harpswell, Maine, United States
View deal

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Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities on Bailey Island

  • Pet-friendly (51)
  • WiFi (116)
  • TV (104)
  • Kitchen (112)
  • Washing machine (75)
  • Balcony/patio (86)
  • No smoking (115)
  • Parking (6)
  • Air conditioning (44)
  • Fireplace (39)
  • Grill (103)
  • Microwave (108)

Nearly half of the vacation rentals on Bailey Island are pet-friendly, which makes it the perfect vacation destination for pet owners. Also, pet-friendly accommodations on Bailey Island cost, on average, $541 per night. If you prefer to stay central, Nearly half of the pet-friendly rentals are less than 2 miles away from the city center.

Information about vacation rentals on Bailey Island

🏡 Vacation rentals available 116 rentals
🌙 Nightly prices starting at $133
⭐ Popular amenities Pets allowed, Internet and TV
🐾 Pet friendly homes 49 homes

Frequently Asked Questions

What is the typical price per night for a vacation home on Bailey Island?

On average, vacation rentals on Bailey Island cost around $133 per night. Nightly prices for house rentals are $625 on average. Cottages on Bailey Island cost on average $436 per night.

How many vacation homes are available for booking on Bailey Island?

There are currently 116 vacation rentals available for booking for your vacation.

What amenities are most popular for vacation homes on Bailey Island?

Most travelers look for Internet, Pets allowed, and TV when booking a vacation rental on Bailey Island.

Are pets allowed in vacation homes on Bailey Island?

In case if you are traveling with a pet on Bailey Island - 42% of vacation rentals are pet-friendly.

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