Romantic Hotels & Resorts in Bailey Island from NZ$149

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Bailey Island Romantic Hotels

Tonight
8 Jan - 9 Jan
Tomorrow
9 Jan - 10 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Bailey Island romantic hotels

Breakfast, dinner and brunch served
The Brunswick Hotel

The Brunswick Hotel

The Brunswick Hotel
3.0 star property
Brunswick
9.4 out of 10, Exceptional, (895)
"Very friendly staff, clean room with comfortable bed, nice reception area with fireplace and place to do a little work."
United States
Pam
The price is NZ$207
includes taxes & fees
11 Jan - 12 Jan
The Brunswick Hotel
Exterior
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine
3.5 star property
Portland
9.4 out of 10, Exceptional, (1142)
"The room was very clean, amenities were great, and staff was helpful and friendly. "
United States
Ethan
The price is NZ$188
includes taxes & fees
25 Jan - 26 Jan
Embassy Suites by Hilton Portland Maine
Exterior
The Harraseeket Inn & Event House Freeport Downtown

The Harraseeket Inn & Event House Freeport Downtown

The Harraseeket Inn & Event House Freeport Downtown
3.5 star property
Freeport
9.4 out of 10, Exceptional, (881)
"Great stay "
United States
Sofia
The price is NZ$215
includes taxes & fees
19 Jan - 20 Jan
The Harraseeket Inn & Event House Freeport Downtown
Exterior
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront
2.5 star property
Downtown Portland
8.8 out of 10, Excellent, (1001)
"Clean rooms, nice staff, convenient location, and great breakfast. "
United States
Jeremy
The price is NZ$171
includes taxes & fees
14 Jan - 15 Jan
Hampton Inn Portland Downtown - Waterfront
Tapas bar
AC Hotel Portland Downtown/Waterfront, ME

AC Hotel Portland Downtown/Waterfront, ME

AC Hotel Portland Downtown/Waterfront, ME
3.5 star property
East Bayside
9.2 out of 10, Wonderful, (1001)
"Love this hotel. "
United States
Gabriella
The price is NZ$167
includes taxes & fees
21 Jan - 22 Jan
AC Hotel Portland Downtown/Waterfront, ME
Exterior
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
4.0 star property
Downtown Portland
9.0 out of 10, Wonderful, (1451)
"Great location for a night out in Portland clean comfortable rooms. "
United States
Kimberly
The price is NZ$149
includes taxes & fees
11 Jan - 12 Jan
Holiday Inn Portland-By the Bay by IHG
Children’s activities
Inn By The Sea

Inn By The Sea

Inn By The Sea
4.0 star property
Cape Elizabeth
9.4 out of 10, Exceptional, (294)
"Room was ready early friendly staff and room is better than expected "
United States
Jeff
Inn By The Sea
Bar (on property)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront
4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1000)
"Lovely staff, room, and great location!"
United States
Kali
The price is NZ$215
includes taxes & fees
2 Feb - 3 Feb
Canopy by Hilton Portland Waterfront
Breakfast, lunch, dinner served; American cuisine
The Westin Portland Harborview

The Westin Portland Harborview

The Westin Portland Harborview
4.0 star property
Downtown Portland
8.8 out of 10, Excellent, (1001)
"Spotless rooms, very roomy bathrooms, great staff"
United States
Kerrie
The price is NZ$189
includes taxes & fees
25 Jan - 26 Jan
The Westin Portland Harborview
Front of property
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa
3.5 star property
Downtown Portland
9.4 out of 10, Exceptional, (1573)
"I love the hotel!"
United States
Christine
Portland Regency Hotel & Spa
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.
View all properties

Top Bailey Island Hotel Reviews

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Yes"
Suzette 1-night trip
Posted 11 hours ago
Embassy Suites by Hilton Portland Maine

Frequently asked questions

Searching for romantic hotels in Bailey Island?
Are you and your partner looking for a romantic holiday? If you'd like to explore some of the area's notable sights, you might make a stop by Cobwork Bridge, Bailey Island Bridge or Land's End Gift Shop. If you're interested in staying close to a certain attraction, you can sort by neighbourhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Bailey Island?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Bailey Island: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Bailey Island are January, March, February and December, with each month seeing an average of 19 cm of snowfall.
What is there to do in Bailey Island?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Bailey Island. A visit to Cobwork Bridge, Bailey Island Bridge or Land's End Gift Shop might be just the ticket when you're checking out the sights.
What's the best way to get to Bailey Island and around town during my romantic getaway?
This information about transportation options in Bailey Island might help your romantic trip get off to a smooth start: Make your way to Bailey Island with a flight to Portland, ME (PWM-Portland Intl. Jetport), which is the closest major airport located 17 mi (27.3 km) from the city centre. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia