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

Romantic Hotels & Resorts in Bailey Island from NZ$308

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Check availability on Bailey Island Romantic Hotels

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for Bailey Island romantic hotels

Property grounds
Smart TV, fireplace, books
Smart TV, fireplace, books
2 bedrooms, desk, iron/ironing board, travel cot

1. Centerview cottage

Centerview cottage
Harpswell
United States
Erin
NZ$786
includes taxes & fees
29 Aug - 30 Aug
Centerview cottage
Interior
2 bedrooms, in-room safe, iron/ironing board, free WiFi
Property grounds
Coffee/tea maker, fridge, microwave, oven

2. 2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
United States
Stacy
NZ$556
includes taxes & fees
21 Sept - 22 Sept
2King Bed BR Private Apt Downtown Brunswick
Property grounds
Exterior detail
Interior
1 bedroom, desk, iron/ironing board, free WiFi

3. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
United States
michael
NZ$308
includes taxes & fees
5 Sept - 6 Sept
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Coffee/tea maker, fridge, microwave, oven
Interior
Coffee/tea maker, fridge, microwave, oven
2 bedrooms, desk, free WiFi, bed sheets

4. 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$828
includes taxes & fees
7 Sept - 8 Sept
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Exterior detail
1 bedroom, iron/ironing board, free WiFi, bed sheets
Interior
Smart TV, books

5. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
United States
Kiernan
NZ$569
includes taxes & fees
24 Aug - 25 Aug
Adorable Portland getaway on the Eastern Promenade
Exterior detail
Smart TV, books
2 bedrooms, desk, iron/ironing board, free WiFi
Smart TV, books

6. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
United States
Cynthia
NZ$777
includes taxes & fees
1 Sept - 2 Sept
Glorious getaway on Portland's Eastern Promenade.
Outdoor dining
Smart TV, books
Exterior detail
Interior

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

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
United States
Richard D.
NZ$1,140
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
Interior
Coffee/tea maker, fridge, microwave, oven
Coffee/tea maker, fridge, microwave, oven
Coffee/tea maker, fridge, microwave, oven

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

Completely remodeled 2 bedroom apartment in Portland's West End
West End
United States
Todd M.
NZ$904
includes taxes & fees
24 Aug - 25 Aug
Completely remodeled 2 bedroom apartment in Portland's West End
Property grounds
Interior
Exterior
Coffee/tea maker, fridge, microwave, oven

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$967
includes taxes & fees
24 Aug - 25 Aug
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Interior
TV
Coffee/tea maker, fridge, microwave, oven
2 bedrooms, iron/ironing board, WiFi, bed sheets

10. Old Port Penthouse Suite - Amazing Harbor Views

Old Port Penthouse Suite - Amazing Harbor Views
Downtown Portland
United States
Lisa G.
NZ$2,251
includes taxes & fees
16 Sept - 17 Sept
Old Port Penthouse Suite - Amazing Harbor Views
View all properties

Top Bailey Island Hotel Reviews

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent
"Il a fallu appeler un membre du personel pour venir nous a frapper la tuyauterie afin d avoir de l eau chaise."
Jean Claude 1-night trip
Posted 5 hours ago
Spark by Hilton Portland Airport Maine Mall
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Great location (near shops, restaurants and bars). The bed was extremely comfortable."
Patsy 6-night trip
Posted 15 hours ago
Portland Regency Hotel & Spa
Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"Room was clean although quite compact."
Maureen 1-night trip
Posted 1 day ago
Inn at St John Portland In-Town
The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Friendly welcome staff. Clean room."
Hiram 1-night trip
Posted 2 days ago
The Westin Portland Harborview

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, Mackerel Cove or Cobwork Bridge. 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, Mackerel Cove or Cobwork Bridge 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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