Holiday Homes in Bailey Island
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Featured Holiday Homes in Bailey Island
Our top choices for Bailey Island holiday homes

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
9.6 out of 10, Exceptional, (38)

Captain's Quarters 2BR Apartment. Walk to Everything!
Captain's Quarters 2BR Apartment. Walk to Everything!
8.6 out of 10, Excellent, (7)
The price is NZ$404
includes taxes & fees
1 Sept - 2 Sept

Fantastic Waterfront Views
Fantastic Waterfront Views
9.8 out of 10, Exceptional, (7)
The price is NZ$746
includes taxes & fees
12 Sept - 13 Sept

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
7.6 out of 10, Good, (13)
The price is NZ$245
includes taxes & fees
3 Sept - 4 Sept

Spacious 4-bedroom house located in the heart of Portland, ME.
Spacious 4-bedroom house located in the heart of Portland, ME.
10.0 out of 10, Exceptional, (1)
The price is NZ$1,509
includes taxes & fees
17 Sept - 18 Sept

On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
10.0 out of 10, Exceptional, (65)

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
9.8 out of 10, Exceptional, (78)

Oceanside escape 🌊 perfect family getaway!
Oceanside escape 🌊 perfect family getaway!
9.8 out of 10, Exceptional, (18)
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Bailey Island Hotel Reviews
Find out more about Bailey Island
Find out more about Bailey Island
Bailey Island Holiday Homes information
Number of reviews | |
---|---|
Accommodation | 632 Holiday Homes |
Lowest Price | NZ$245 |
Highest Price | NZ$1,509 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
More accommodation types in Bailey Island
All Accommodation Types
Be inspired: Top Holiday Homes destinations in 2025
- New Zealand Holiday Houses
- Auckland Holiday Houses
- Hanmer Springs Holiday Houses
- Rarotonga Holiday Houses
- Queenstown Holiday Houses
- Gold Coast Holiday Houses
- Rotorua Holiday Houses
- Taupo Holiday Houses
- Nelson Holiday Houses
- Christchurch Holiday Houses
- Wellington Holiday Houses
- Fiji Holiday Houses
- Wanaka Holiday Houses
- Kaikoura Holiday Houses
- Akaroa Harbour Holiday Houses
- Tauranga Holiday Houses
- Mount Maunganui Holiday Houses
- Dunedin Holiday Houses
- Hamilton Holiday Houses
- Napier Holiday Houses