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

Vacation rentals on Bailey Island

Browse 122 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+

  • 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 122 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Bailey Island
House ∙ 10 guests ∙ 6 bedrooms

Child-friendly house with barbecue, patio & yard | Nature view | Pets are welcome

Bailey Island, Harpswell, Maine, United States
This waterfront house rental on Orr's Island features a kitchen, fireplace, and yard, perfect for family gatherings with pets.
from $1,218
per night
Outstanding(32 ratings)
from $1,218
per night
View deal
House Bailey Island
House ∙ 14 guests ∙ 6 bedrooms

House with garden, barbeque & patio | City view

Bailey Island, Harpswell, Maine, United States
This house rental on Bailey Island features a fireplace, spa, and mountain views, accommodating up to 14 guests with pets welcome.
from $831
per night
Outstanding(99 ratings)
from $831
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with BBQ

Bailey Island, Harpswell, Maine, United States
This Harpswell cabin features a kitchen, balcony, and parking, perfect for families seeking a memorable getaway.
from $297
per night
Outstanding(8 ratings)
from $297
per night
View deal
House Bailey Island
House ∙ 5 guests ∙ 3 bedrooms

Vacation home with BBQ, garden & patio | Nature view

Bailey Island, Harpswell, Maine, United States
This Harpswell house rental features a yard, fireplace, and spa, perfect for families and pets seeking a memorable getaway.
from $253
per night
Outstanding(96 ratings)
from $253
per night
View deal
Cabin Bailey Island
Cabin ∙ 6 guests ∙ 3 bedrooms

Family-oriented lovely cottage with barbecue

Bailey Island, Harpswell, Maine, United States
This cabin in South Harpswell offers waterfront access, a cozy fireplace, and a balcony perfect for family gatherings.
from $523
per night
Outstanding(32 ratings)
from $523
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with barbeque, patio & yard | Nature view

Bailey Island, Harpswell, Maine, United States
from $308
per night
Outstanding(59 ratings)
from $308
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with garden, terrace & BBQ

Bailey Island, Harpswell, Maine, United States
This Harpswell cabin offers waterfront access, a fireplace, a kitchen, and a yard, perfect for a family getaway with pets.
from $234
per night
Outstanding(187 ratings)
from $234
per night
View deal
House Bailey Island
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden, barbeque & patio | Nature view

Bailey Island, Harpswell, Maine, United States
This waterfront house rental on Orr's Island features a yard, fireplace, and kitchen, perfect for a relaxing getaway with pets.
from $209
per night
Outstanding(44 ratings)
from $209
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 $308
per night
from $308
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 $324
per night
Excellent(22 ratings)
from $324
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 $136
per night
Outstanding(34 ratings)
from $136
per night
View deal
Cabin Bailey Island
Cabin ∙ 2 guests ∙ 2 bedrooms

Fully equipped nice cottage with grill, garden & patio | Beach nearby | Perfect for remote work

Bailey Island, Harpswell, Maine, United States
This Harpswell cabin offers beachfront access, a kitchen, a yard, and parking, perfect for a romantic getaway for two.
from $219
per night
Outstanding(92 ratings)
from $219
per night
View deal
House Bailey Island
House ∙ 15 guests ∙ 6 bedrooms

House with barbecue, patio & yard | Good for workation

Bailey Island, Harpswell, Maine, United States
This Harpswell house rental offers a kitchen, yard, and parking, perfect for family gatherings of up to 15 guests.
from $627
per night
Outstanding(4 ratings)
from $627
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 $150
per night
Outstanding(54 ratings)
from $150
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 $216
per night
Outstanding(175 ratings)
from $216
per night
View deal

Vacation rentals and apartments with air conditioning

House Bailey Island
from $446
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-friendly house with barbecue | Nature view

5.0
Outstanding(10 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
Cabin Bailey Island
from $650
per night
Cabin ∙ 12 guests ∙ 5 bedrooms

Cottage with BBQ, garden & terrace | Suitable for remote work

5.0
Outstanding(119 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
House Bailey Island
from $289
per night
House ∙ 6 guests ∙ 3 bedrooms

House with patio & grill

5.0
Outstanding(10 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

Cabin Bailey Island
from $249
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
View deal
Cabin Bailey Island
from $632
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
View deal
House Bailey Island
from $353
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

Vacation Rentals With Fireplaces

House Bailey Island
from $1,244
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with yard & grill | Good for workation

5.0
Outstanding(59 ratings)
Bailey Island, Harpswell, Maine, United States
Fireplace
View deal
Cabin Bailey Island
from $302
per night
Cabin ∙ 7 guests ∙ 4 bedrooms

Cottage with BBQ, yard & terrace | Nature view

4.9
Outstanding(65 ratings)
Bailey Island, Harpswell, Maine, United States
Fireplace
View deal
Cabin Bailey Island
from $444
per night
Cabin ∙ 7 guests ∙ 4 bedrooms

Cottage with terrace, grill & yard

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

Budget-friendly rental options

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

Apartment Bailey Island
from $139
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment with patio & garden

4.9
Outstanding(71 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
House Bailey Island
from $746
per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, garden & barbeque | Perfect for remote work

5.0
Outstanding(29 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
House Bailey Island
from $257
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

House Bailey Island
from $447
per night
House ∙ 8 guests ∙ 4 bedrooms

House with patio & grill | Nature view

4.9
Outstanding(14 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
Cabin Bailey Island
from $477
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 $229
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with grill, garden & terrace | Nature view

4.9
Outstanding(33 ratings)
Bailey Island, Harpswell, Maine, United States
View deal

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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.

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Price clarity, no surprises

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

Smart search made simple

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

Find your dream stay

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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, $550 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 121 rentals
🌙 Nightly prices starting at $137
⭐ Popular amenities Pets allowed, Internet and TV
🐾 Pet friendly homes 51 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 $137 per night. Nightly prices for house rentals are $656 on average. Cottages on Bailey Island cost on average $461 per night.

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

There are currently 121 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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