Name: DoubleTree by Hilton Boston North Shore
Price range: CA $151

Gloucester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Encore Boston Harbor

per person

Jul. 29 - Jul. 31

found 13 hours ago

Roundtrip flight included

Montreal (YUL) to Boston (BOS)

Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

per person

Jul. 24 - Jul. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.

Boston Harbor Hotel

North End

Save 100% on your flight

per person

Jul. 10 - Jul. 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

The Langham, Boston

Downtown Boston

per person

Jul. 27 - Jul. 30

found 13 hours ago

Roundtrip flight included

Montreal (YUL) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.

Global Luxury Suites Downtown Boston

Chinatown

per person

Jul. 10 - Jul. 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 4-star business-friendly aparthotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a 24-hour business center. Our guests praise the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.

Top Gloucester hotels deals

Beauport Hotel Gloucester

55 Commercial Street, Gloucester, MA

CA $327

CA $366 total

includes taxes & fees

May 12 - May 13

Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Pavilion Beach and Gloucester Unitarian Universalist Church are located nearby.

Pool

Free WiFi

Ocean House Hotel at Bass Rocks

107 Atlantic Rd, Gloucester, MA

Free cancellation

Reserve now, pay when you stay

CA $207

CA $264 total

includes taxes & fees

May 12 - May 13

Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Good Harbor Beach and The Gorton Theatre are located nearby.

Pool

Hot tub

Castle Manor Inn

141 Essex Avenue, Gloucester, MA

CA $275

CA $307 total

includes taxes & fees

May 7 - May 8

Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stage Fort Park and Half Moon Beach are located nearby.

Parking included

Free WiFi

The Vista

22 Thatcher Rd., Gloucester, MA

CA $242

CA $270 total

includes taxes & fees

May 15 - May 16

Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Good Harbor Beach and Schooner Adventure are located nearby.

Pool

Breakfast included

Beach Life Bliss - steps to the beach

CA $216

CA $540 total

includes taxes & fees

May 21 - May 22

Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and patios. Popular attractions Plum Cove Beach and Halibut Point Reservation are located nearby.

Kitchen

Washer

DoubleTree by Hilton Boston North Shore

50 Ferncroft Rd, Danvers, MA

CA $151

CA $169 total

includes taxes & fees

May 25 - May 26

Stay at this 4-star golf hotel in Danvers. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Water Park of New England and Glen Magna Farms are located nearby.

Pool

Spa

Don't see what you're looking for?

See all available properties in Gloucester

View all properties

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.

Popular places to visit

Wingaersheek Beach

Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.

Good Harbor Beach

If a restful vacation is part of your travel plans, Good Harbor Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

Hammond Castle

You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your trip to Gloucester. Wander the beautiful beaches and seaside in the area.

Gloucester Vacations

Are you all ready for your adventure? Make sure you don't miss out on any fun in Gloucester by knowing a few facts about it before you fly off.

To help you find your feet, Gloucester is 25 miles (40 kilometers) to the northeast of the noteworthy city of Boston.

With plenty of things to do in this corner of North Shore, it's not hard to see why 29,000 locals choose to call it home.

Places to visit in Gloucester

Of all the roads you take in life, make sure at least a few are made of dirt! So slip into those boots, dig out your water bottle and tackle the walks of Dogtown. Seeking some more options? Traipse through the very old corridors of Hammond Castle. This grand fortification offers an educational day trip for the whole family. And that's not all. Connect with nature at Ravenswood Park and admire the great work they're doing to protect our native plants and animals.

Where do you fly into for Gloucester?

Coming in to land at Logan International Airport (BOS)? After you've jumped off the plane and claimed your suitcase, the heart of Gloucester will be just 25 miles (40 kilometers) to the northeast from here.