Romantic Hotels & Resorts in Bailey Island from NZ$168

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Check availability on Bailey Island Romantic Hotels

Tonight
23 Feb - 24 Feb
Tomorrow
24 Feb - 25 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

Our top choices for Bailey Island romantic hotels

Front of property – evening/night

Inn On Peaks Island

Inn On Peaks Island
3.0 star property
Peaks Island
9.0 out of 10, Wonderful, (107 reviews)
"Excellent little getaway in a very quaint island!"
United States
Kellie Slate
The price is NZ$199
includes taxes & fees
24 Feb - 25 Feb
Inn On Peaks Island
Breakfast, dinner and brunch served

The Brunswick Hotel

The Brunswick Hotel
3.0 star property
Brunswick
9.4 out of 10, Exceptional, (914 reviews)
"The staff was kind and knowledgeable and the room was perfect. We will definitely stay here again!"
United States
Jennifer
The Brunswick Hotel
Exterior

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, (895 reviews)
"Really great location."
United States
Carissa
The price is NZ$217
includes taxes & fees
24 Feb - 25 Feb
The Harraseeket Inn & Event House Freeport Downtown
Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (125 reviews)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is NZ$430
includes taxes & fees
24 Feb - 25 Feb
City Amenities, Casco Bay Sunrises and Natural Beauty
Outdoor pool, a heated pool, open 9:00 AM to 10:00 PM, pool loungers

Best Western Merry Manor Inn

Best Western Merry Manor Inn
2.5 star property
Highland
9.0 out of 10, Wonderful, (1,010 reviews)
"Very pleased with our stay!"
United States
Amanda
The price is NZ$168
includes taxes & fees
2 Mar - 3 Mar
Best Western Merry Manor Inn
Children’s activities

Inn By The Sea

Inn By The Sea
4.0 star property
Cape Elizabeth
9.4 out of 10, Exceptional, (299 reviews)
"Room was ready early friendly staff and room is better than expected "
United States
Jeff
Inn By The Sea
Lobby

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine
3.5 star property
Portland
9.4 out of 10, Exceptional, (1,157 reviews)
"Nice hotel, great breakfast."
United States
Shannon
The price is NZ$203
includes taxes & fees
15 Mar - 16 Mar
Embassy Suites by Hilton Portland Maine
Tapas bar

AC Hotel Portland Downtown/Waterfront, ME

AC Hotel Portland Downtown/Waterfront, ME
3.5 star property
East Bayside
9.2 out of 10, Wonderful, (1,002 reviews)
"Great all around stay "
United States
Matthew
The price is NZ$168
includes taxes & fees
12 Mar - 13 Mar
AC Hotel Portland Downtown/Waterfront, ME
Reception

Longfellow Hotel

Longfellow Hotel
4.0 star property
Parkside
9.6 out of 10, Exceptional, (147 reviews)
"We loved our stay. Great staff, room was nice, cafe very good and the Town Car service for rides, so convenient!"
United States
Rosanne
Longfellow Hotel
Front of property

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa
3.5 star property
Downtown Portland
9.4 out of 10, Exceptional, (1,588 reviews)
"The room was impeccable, the restaurant was delicious and perfect location"
United States
Elvira
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.
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Top Bailey Island Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"I always enjoy staying at this charming hotel. Its rustic setting and cheerful staff make my Portland visits comforting and memorable. "
Michael 2-night trip
Posted 2 days ago
Inn at St John Portland In-Town

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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