Find Romantic Hotels in Gloucester, MA

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Check availability on Gloucester Romantic Hotels

Our top choices for Gloucester romantic hotels

Rooftop pool
Beauport Hotel Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester
3.5 star property
Downtown Gloucester
9.6 out of 10, Exceptional, (906)
"We loved our stay So comfy, clean and beautiful views! "
United States
Steven
Beauport Hotel Gloucester
Reception
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina
3.5 star property
Gloucester
8.4 out of 10, Very Good, (777)
"Lovely hotel "
United States
Ryan
The price is NT$6,707
NT$7,492 total
includes taxes & fees
Dec 15 - Dec 16
The Hotel at Cape Ann Marina
Lobby sitting area
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore
4.0 star property
Danvers
8.0 out of 10, Very Good, (2299)
"Great stay!"
United States
Stephanie
The price is NT$3,044
NT$3,400 total
includes taxes & fees
Jan 2 - 2026/1/3
DoubleTree by Hilton Boston North Shore
Lobby
Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2200)
"The room was clean and the staff was very friendly "
United States
Troyce
The price is NT$2,890
NT$3,415 total
includes taxes & fees
Dec 27 - Dec 28
Comfort Inn & Suites Logan International Airport
Beach
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College
3.5 star property
Beverly
9.2 out of 10, Wonderful, (1140)
"Clean room, great staff and service, very easy check in, I always stay here when visiting my son and daughter in law"
United States
Brian
The price is NT$2,940
NT$3,284 total
includes taxes & fees
Jan 4 - 2026/1/5
The Wylie Inn and Conference Center at Endicott College
Property amenity
Rockport Inn And Suites

Rockport Inn And Suites

Rockport Inn And Suites
2.5 star property
Rockport
8.6 out of 10, Excellent, (1552)
"Just a nice place to stay. Free breakfast too!"
United States
Carrie
Rockport Inn And Suites
Dinner and brunch served
Briar Barn Inn

Briar Barn Inn

Briar Barn Inn
3.5 star property
Rowley
9.6 out of 10, Exceptional, (746)
"So comfortable. I want to stay again and try the restaurant!"
United States
Natasha
Briar Barn Inn
Property grounds
The Yankee Clipper Inn

The Yankee Clipper Inn

The Yankee Clipper Inn
3.5 star property
Rockport
9.0 out of 10, Wonderful, (375)
"Beautiful property with amazing view. Very convenient location, breakfast was amazing! "
United States
Julie
The price is NT$5,902
NT$6,592 total
includes taxes & fees
Dec 18 - Dec 19
The Yankee Clipper Inn
2 restaurants, breakfast, lunch, dinner served; American cuisine
Hawthorne Hotel

Hawthorne Hotel

Hawthorne Hotel
3.5 star property
Downtown Salem
9.4 out of 10, Exceptional, (1514)
"Great customer service, very clean rooms and amazing food! Will definitely be staying here again! "
United States
Samantha
Hawthorne Hotel
Property amenity
Boston Marriott Peabody

Boston Marriott Peabody

Boston Marriott Peabody
3.5 star property
South Peabody
8.8 out of 10, Excellent, (1005)
"Great place to stay. "
United States
LeAnn
The price is NT$4,741
NT$5,296 total
includes taxes & fees
Dec 20 - Dec 21
Boston Marriott Peabody
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 Gloucester Hotel Reviews

Red Roof Inn PLUS+ Boston - Logan

Red Roof Inn PLUS+ Boston - Logan

10/10 Excellent
"The room was clean, I don’t know why they have lower rating! Few things missing no gym, no big spacious waiting area."
oscar 1-night trip
Posted 4 days ago
Red Roof Inn PLUS+ Boston - Logan

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Frequently asked questions

Searching for romantic hotels in Gloucester?
Are you looking for a romantic getaway? Our guests also love Gloucester for its beautiful ocean views and whale watching. If you'd like to explore some of the area's notable sights, you might make a stop by Capt Bill & Sons Whale Watch, Cape Ann Museum, or Maritime Gloucester. If you're interested in staying near a particular destination, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Gloucester?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Gloucester: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 34°F. The snowiest months in Gloucester are January, February, December, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Gloucester?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all that Gloucester has to offer. Couples looking for a little of everything will enjoy Gloucester for its historic landmarks, whale watching, and seaside. You might think about stopping by Capt Bill & Sons Whale Watch, Cape Ann Museum, or Maritime Gloucester while you're seeing the sights.
What's the best way to get to Gloucester and around town during my romantic getaway?
This information about transportation options in Gloucester might help your romantic trip get off to a smooth start: To get to Gloucester, book a flight to Beverly, MA (BVY-Beverly Municipal), which is the closest major airport, located 12.8 mi (20.6 km) from the city center. To explore the surrounding area, ride one of the trains from Gloucester Station or West Gloucester Station.