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

Romantic Hotels & Resorts in Bailey Island from NZ$367

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Check availability on Bailey Island Romantic Hotels

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Bailey Island romantic hotels

Exterior

West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (95 reviews)
"Wonderful staff and scrumptious breakfast "
United States
Elena
The price is NZ$420
includes taxes & fees
13 July - 14 July
West End Collection at 146 Pine
Panoramic Room, 1 King Bed, Balcony, Ocean View (Pier Building) | Terrace/patio

Smuggler's Cove Inn

Smuggler's Cove Inn
2.5 star property
East Boothbay
9.0 out of 10, Wonderful, (489 reviews)
"Great Sunday Brunch"
United States
Barbara
The price is NZ$499
includes taxes & fees
23 July - 24 July
Smuggler's Cove Inn
Restaurant

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn
3.0 star property
Ocean Point
8.8 out of 10, Excellent, (573 reviews)
"Friendly staff, beautiful/clean room, and the ocean view was amazing."
United States
marcie
The price is NZ$468
includes taxes & fees
29 July - 30 July
Bluebird Ocean Point Inn
Deluxe Double Room, 1 King Bed, Bay View | Balcony

Linekin Bay Resort

Linekin Bay Resort
3.0 star property
Boothbay Harbor
9.2 out of 10, Wonderful, (220 reviews)
"Great place, beautiful property. -Great breakfast and restaurant! Can't wait to come back"
United States
renee
The price is NZ$675
includes taxes & fees
22 July - 23 July
Linekin Bay Resort
2 restaurants; breakfast, lunch and dinner served

Spruce Point Inn

Spruce Point Inn
3.5 star property
Boothbay Harbor
8.8 out of 10, Excellent, (415 reviews)
"Loved the property. wonderful people. But no information was given to us about the property ie where the pools were located"
United States
Rose Sgarlat
The price is NZ$979
includes taxes & fees
13 July - 14 July
Spruce Point Inn
Exterior

Boothbay Harbor Inn

Boothbay Harbor Inn
2.5 star property
Boothbay Harbor
8.4 out of 10, Very good, (1,005 reviews)
"The staff was very friendly and helpful. The location was great!"
United States
Lolita
The price is NZ$516
includes taxes & fees
22 July - 23 July
Boothbay Harbor Inn
Triple Queen Suite Overlooking Whale Park | Balcony view

Fishermans Wharf Inn

Fishermans Wharf Inn
2.5 star property
Boothbay Harbor
8.6 out of 10, Excellent, (908 reviews)
"Very peaceful looking over the water and a close walk to everything."
United States
Vicky
The price is NZ$545
includes taxes & fees
22 July - 23 July
Fishermans Wharf Inn
Superior Room, 1 King Bed

The Thistle Inn

The Thistle Inn
2.0 star property
Boothbay Harbor
7.6 out of 10, Good, (90 reviews)
"Beautiful Boothbay Harbor!"
United States
Charles
The price is NZ$365
includes taxes & fees
6 Aug - 7 Aug
The Thistle Inn
Two Queen Marina Front | Exterior

Tugboat Inn

Tugboat Inn
3.0 star property
Boothbay Harbor
9.0 out of 10, Wonderful, (1,006 reviews)
"The views of the harbor just sitting on deck outside your room are amazing!!!"
United States
Michael
The price is NZ$547
includes taxes & fees
26 July - 27 July
Tugboat Inn
Terrace/patio

Greenleaf Inn

Greenleaf Inn
2.0 star property
Boothbay Harbor
9.2 out of 10, Wonderful, (17 reviews)
"Our host is the best! Such a beautiful property. "
United States
Lee
The price is NZ$966
includes taxes & fees
13 July - 14 July
Greenleaf Inn
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Loved the place but the AC could not keep up with the heat. Room was 75 degrees."
Justin 2-night trip
Posted 1 hour ago
Portland Regency Hotel & Spa

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.

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