A rocky shoreline with a boat, a house, and a forest in the background.

Romantic Hotels & Resorts in Bailey Island from NZ$320

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Check availability on Bailey Island Romantic Hotels

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Bailey Island romantic hotels

A wooden house with a deck and a stone pathway leading to a grassy area.
An aerial view of a two-story house with a large deck, surrounded by dense forest.
A bedroom with a wooden bed, two bedside tables, a nightstand, a wooden desk, and a door.
A wooden hallway with built-in shoe racks and a metal coffee table.

1. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
United States
Hana L.
NZ$478
includes taxes & fees
20 Oct - 21 Oct
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A wooden deck with a view of a lake, surrounded by trees and shrubs.
A kitchen with wooden cabinets, a stove, a refrigerator, and a dining table with chairs.
A staircase with wooden steps and white walls, leading to an upper floor.
A cabin room with a bed, a chair, a desk, and large windows with blinds.

2. Centerview cottage

Centerview cottage
Harpswell
United States
Catherine G.
NZ$826
includes taxes & fees
14 Oct - 15 Oct
Centerview cottage
A modern kitchen with a dishwasher, a dining area with chairs, and a red refrigerator.
A bridge over a river with a building on the right.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining area.
A street with storefronts, including a hair salon and a natural foods shop.

3. 2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
United States
caralyn g.
NZ$539
includes taxes & fees
12 Oct - 13 Oct
2King Bed BR Private Apt Downtown Brunswick
A wooden staircase with a wooden railing, surrounded by green foliage.
A living room with a wooden chair, a blue patterned sofa, a television, and bookshelves.
A porch with a rocking chair and a metal bench with decorative plates.
A bedroom with a navy blue bedspread, two matching pillows, a navy blue and white anchor-patterned rug, and two bedside tables with lamps.

4. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
United States
michael
NZ$320
includes taxes & fees
12 Oct - 13 Oct
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.
A bridge over a river with a building on the right.
A modern kitchen with white cabinets, a central island with stools, a microwave, and a large window.
A bedroom with two beds, a desk, and a chair. There are windows with blinds, a painting on the wall, and a vase with dried plants.

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

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
United States
Britta M.
NZ$731
includes taxes & fees
2 Nov - 3 Nov
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
A street lined with buildings, one with a red door and a sign that reads "MINATO".
A cozy room with a wooden table, a sofa, a bookshelf, and a window with a view.
A restaurant interior with tables and chairs, a bar area, and shelves with bottles.
A kitchen with a wooden island, two stools, a refrigerator, and a hanging light fixture.

6. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
United States
Kiernan
NZ$498
includes taxes & fees
26 Oct - 27 Oct
Adorable Portland getaway on the Eastern Promenade
A street lined with buildings, one with a red door and a sign that reads "MINATO".
A living room with a sofa, armchairs, a coffee table, and a potted plant.
A neatly made bed with white linens and pillows, a bedside lamp, and a framed artwork on the wall.
A living room with a white sofa, a small table with a potted orchid, a bookshelf, and a radiator.

7. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
United States
William
NZ$833
includes taxes & fees
18 Oct - 19 Oct
Glorious getaway on Portland's Eastern Promenade.
A two-story house with a balcony, a covered patio, and a fenced yard.
A living room with a gray sofa, two pink armchairs, a wooden coffee table, and a colorful rug.
A dining area with a wooden table, four chairs, a hanging light fixture, and a window with curtains.
A house with a black front door, white trim, and a number '106' above the door. There are two flower pots on the steps.

8. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
United States
Richard D.
The Globe House on Munjoy Hill - Walk to Breweries
A dirt path in a park with autumn foliage.
A wooden cabin interior with a dining area, a sofa, a kitchen, and large windows.
A wooden cabin-style kitchen with a large island, built-in appliances, and a view of the forest.
A rustic cabin with a red door, surrounded by trees with autumn foliage.

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

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
United States
Genevieve W.
NZ$1,080
includes taxes & fees
13 Oct - 14 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A modern kitchen with a central island, a dining area with a sofa and coffee table, and large windows providing natural light.
A modern kitchen with a central island, bar stools, a refrigerator, a microwave, and a brick wall backsplash.
A modern kitchen with a central island, white bar stools, stainless steel appliances, and a brick backsplash.
A modern kitchen with a stainless steel refrigerator, a microwave, a gas stove, and a sink. There are three white bar stools and a large pendant light above the island.

10. Completely remodeled 2 bedroom apartment in Portland's West End

Completely remodeled 2 bedroom apartment in Portland's West End
West End
United States
Deborah
NZ$1,068
includes taxes & fees
18 Oct - 19 Oct
Completely remodeled 2 bedroom apartment in Portland's West End
View all properties

Top Bailey Island Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"The inn itself was beautifully kept. The water pressure was great. There was plenty of hot water except very early in the morning (before 6am). I didn’t walk in the area but if I had too, I wouldn’t feel comfortable in the evening. There was parking behind the hotel and I was lucky to get a spot both nights that I was there otherwise you would have to park in their other lot somewhere around the corner. They had lemon water, fruit, cookies, tea and coffee out all the time. The included breakfast was just an easy grab a toasted bagel and go. Nothing special but it was a nice offer. The beds were soft, the AC worked well and our room was very large. Our room was on the second floor, no elevator and extremely steep steps, but staff was always available to help with bags or luggage. Overall, a very nice stay and less expensive than closer to town."
Jane 2-night trip
Posted 15 hours ago
Inn at St John Portland In-Town
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"The room clean and the property was well kept. The included breakfast was solid for a hotel breakfast. My only complaints would be that we didnt have hand soap which took a few tries to track down because the desk staff was away when we came back late night, the other complaint is the elevator door is scary loud but it functions properly, just something wonky with the door"
Phillip 2-night trip
Posted 17 hours ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"The staff was friendly, and the room was clean. There is a restaurant on site, and the location is fantastic and close to everything."
Angela M 1-night trip
Posted 19 hours ago
Portland Regency Hotel & Spa
The Westin Portland Harborview

The Westin Portland Harborview

8/10 Good
"Wonderful, historic building. Clean room. Great staff. Design starting to look a bit dated."
Robert 1-night trip
Posted 21 hours ago
The Westin Portland Harborview
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

10/10 Excellent
"I liked that it had an indoor pool, bar and restaurant."
Wendy 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Portland

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, Land's End Gift Shop or Mackerel Cove. 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, Land's End Gift Shop or Mackerel Cove 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.

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