Romantic Hotels & Resorts in Bailey Island from NZ$214

  • 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

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

Our top choices for Bailey Island romantic hotels

Property grounds

Captain's House 1BR Apt. Walk to everything.

Captain's House 1BR Apt. Walk to everything.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is NZ$214
includes taxes & fees
25 May - 26 May
Captain's House 1BR Apt. Walk to everything.
Interior

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.0 out of 10, Wonderful, (16 reviews)
"The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. "
United States
Michael S.
The price is NZ$477
includes taxes & fees
25 May - 26 May
Little Lincoln beautiful home
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is NZ$811
includes taxes & fees
25 May - 26 May
Centerview cottage
Fridge, microwave, oven, stovetop

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (32 reviews)
" Very spacious, clean and beautiful."
United States
robert p.
The price is NZ$652
includes taxes & fees
25 May - 26 May
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Interior

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.6 out of 10, Excellent, (13 reviews)
"Clean convenient location and quiet with comfortable beds. Just what we needed. "
United States
caralyn g.
The price is NZ$514
includes taxes & fees
31 May - 1 June
2King Bed BR Private Apt Downtown Brunswick
Property grounds

Waterfront Private Apartment, minutes from LLBean!

Waterfront Private Apartment, minutes from LLBean!
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"The room was clean and the area is great for walking with the dog."
United States
Anonymous traveller
The price is NZ$667
includes taxes & fees
7 June - 8 June
Waterfront Private Apartment, minutes from LLBean!
Exterior detail

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (78 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
The price is NZ$885
includes taxes & fees
30 May - 31 May
Elegant condo - walk to Portland's best restaurants & Old Port
Property grounds

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (37 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is NZ$824
includes taxes & fees
30 May - 31 May
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Exterior detail

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (132 reviews)
"The host was very friendly and it was an easy apartment to check into. "
United States
Kendall M.
The price is NZ$470
includes taxes & fees
29 May - 30 May
Adorable Portland getaway on the Eastern Promenade
Property grounds

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is NZ$1,081
includes taxes & fees
25 May - 26 May
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

6/10 Okay
"Under renovation right now. No common area or functional lobby space. Staff was friendly and room was fine and clean enough. Main attraction is the central, walkable location."
Lauren 2-night trip
Posted less than an hour ago
Hyatt Place Portland Downtown - Old Port Square

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 Bailey Island Bridge, Cobwork 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 Bailey Island Bridge, Cobwork 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