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

Vacation rentals on Bailey Island

Browse 136 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 136 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

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 $167
per night
Outstanding(43 ratings)
from $167
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 $228
per night
Outstanding(175 ratings)
from $228
per night
View deal
House Bailey Island
House ∙ 10 guests ∙ 6 bedrooms

Child-friendly wonderful house with yard, barbeque & terrace | Dogs allowed

Bailey Island, Harpswell, Maine, United States
from $493
per night
Outstanding(81 ratings)
from $493
per night
View deal
Cabin Bailey Island
Cabin ∙ 6 guests ∙ 3 bedrooms

Family-oriented lovely cottage with barbecue | Nature view

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 $535
per night
Outstanding(32 ratings)
from $535
per night
View deal
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 $1,140
per night
Outstanding(32 ratings)
from $1,140
per night
View deal
House Bailey Island
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly pleasant house with garden, patio & barbecue | Pets are welcome

Bailey Island, Harpswell, Maine, United States
This waterfront house rental on Bailey Island features a kitchen, balcony, yard, and space for up to seven guests and pets.
from $542
per night
Outstanding(1 rating)
from $542
per night
View deal
House Bailey Island
House ∙ 7 guests ∙ 3 bedrooms

Children-friendly vacation home with grill & patio | Nature view | Pets are welcome

Bailey Island, Harpswell, Maine, United States
This house rental on Orr's Island offers a kitchen, parking, and pet-friendly space for up to seven guests.
from $314
per night
from $314
per night
View deal
House Bailey Island
House ∙ 6 guests ∙ 2 bedrooms

House with garden, patio & barbeque

Bailey Island, Harpswell, Maine, United States
This Harpswell house rental features a yard, fireplace, and kitchen, perfect for families and pets, accommodating up to 6 guests.
from $304
per night
Outstanding(20 ratings)
from $304
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with garden, terrace & BBQ | Nature view

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 $246
per night
Outstanding(187 ratings)
from $246
per night
View deal
House Bailey Island
House ∙ 6 guests ∙ 2 bedrooms

Child-friendly nice vacation home with BBQ & terrace | Nature view

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 $205
per night
Outstanding(22 ratings)
from $205
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 $382
per night
Outstanding(207 ratings)
from $382
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with grill

Bailey Island, Harpswell, Maine, United States
This cozy cabin on Bailey Island offers kitchen amenities, beach access, and waterfront views for a perfect family getaway.
from $235
per night
from $235
per night
View deal
Cabin Bailey Island
Cabin ∙ 12 guests ∙ 5 bedrooms

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

Bailey Island, Harpswell, Maine, United States
This waterfront cabin on Bailey Island features a fireplace, spa, yard, and space for 12, perfect for a family getaway.
from $806
per night
Outstanding(118 ratings)
from $806
per night
View deal
House Bailey Island
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented vacation home with yard, barbecue & terrace | Nature view | Suitable for remote work | Pets are welcome

Bailey Island, Harpswell, Maine, United States
This South Harpswell house rental features a yard, fireplace, and kitchen, perfect for family gatherings with pets welcome.
from $663
per night
from $663
per night
View deal
Cabin Bailey Island
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with barbeque, patio & yard

Bailey Island, Harpswell, Maine, United States
This waterfront cabin in Harpswell features a kitchen, fireplace, yard, and parking, perfect for a family getaway.
from $302
per night
Outstanding(59 ratings)
from $302
per night
View deal

Vacation Rentals With Fireplaces

House Bailey Island
from $1,255
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
House Bailey Island
from $834
per night
House ∙ 14 guests ∙ 6 bedrooms

House with garden, barbeque & patio | City view

4.9
Outstanding(99 ratings)
Bailey Island, Harpswell, Maine, United States
Fireplace
View deal
House Bailey Island
from $287
per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation home with BBQ, garden & patio

4.9
Outstanding(98 ratings)
Bailey Island, Harpswell, Maine, United States
Fireplace
View deal
See all offers

Vacation rentals and apartments with air conditioning

Cabin Bailey Island
from $176
per night
Cabin ∙ 4 guests ∙ 3 bedrooms

Cottage with terrace & BBQ | Close to the beach | Pets allowed

5.0
Outstanding(56 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
House Bailey Island
from $392
per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, barbeque & terrace

4.9
Outstanding(28 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
House Bailey Island
from $474
per night
House ∙ 5 guests ∙ 3 bedrooms

Fully equipped house with terrace, barbeque & garden | Perfect for remote work | Pets are welcome

5.0
Outstanding(28 ratings)
Bailey Island, Harpswell, Maine, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House Bailey Island
from $457
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped charming vacation home with BBQ, patio & yard

5.0
Outstanding(36 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony
View deal
Cabin Bailey Island
from $677
per night
Cabin ∙ 10 guests ∙ 6 bedrooms

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

5.0
Outstanding(10 ratings)
Bailey Island, Harpswell, Maine, United States
Balcony
View deal
House Bailey Island
from $504
per night
House ∙ 11 guests ∙ 5 bedrooms

Vacation home with grill, terrace & garden

4.8
Outstanding(23 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 $494
per night
Cabin ∙ 8 guests ∙ 5 bedrooms

Cottage with yard, barbecue & patio | Nature view

5.0
Outstanding(25 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
Cabin Bailey Island
from $312
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with BBQ

5.0
Outstanding(8 ratings)
Bailey Island, Harpswell, Maine, United States
View deal
House Bailey Island
from $1,133
per night
House ∙ 10 guests ∙ 4 bedrooms

House with grill, patio & yard | Nature view | Good for workation

4.7
Excellent(55 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 $237
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
View deal
Cabin Bailey Island
from $579
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
Condo Bailey Island
from $277
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
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, $564 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 136 rentals
🌙 Nightly prices starting at $88
⭐ Popular amenities Pets allowed, Internet and TV
🐾 Pet friendly homes 57 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 $88 per night. Nightly prices for house rentals are $654 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 136 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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