Gloucester Vacations 2025 from CA $658

Gloucester flight + hotel packages

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

The Beverly

Save 100% on your flight

per person

Apr. 19 - Apr. 24

found 21 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Stay at this 3-star business-friendly hotel in Beverly. Enjoy free WiFi, free parking, and an in-room coffeemaker. Our guests praise the clean rooms in our reviews. Popular attractions Salem Witch Museum and Dogs by Design & Cats Too are located nearby.

Boston Harbor Hotel

North End

Save 100% on your flight

per person

May 22 - May 26

found 9 hours 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 Revolution Hotel

South End

Save 100% on your flight

per person

May 29 - Jun. 1

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Faneuil Hall Marketplace are located nearby.

The Cove At Salem

Save 100% on your flight

per person

Apr. 19 - Apr. 24

found 21 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Stay at this 3-star hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Dead Horse Beach are located nearby.

The Langham, Boston

Downtown Boston

Save 100% on your flight

per person

May 29 - Jun. 1

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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.

Top Gloucester hotels deals

Beauport Hotel Gloucester

55 Commercial Street, Gloucester, MA

CA $292

CA $326 total

includes taxes & fees

17 Mar - 18 Mar

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

Beach Life Bliss - steps to the beach

Get rates

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

Kitchen

Washer

Harborview Inn

71 Western Avenue, Gloucester, MA

CA $272

CA $303 total

includes taxes & fees

17 Mar - 18 Mar

Stay at this 3.5-star B&B in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Fishermen's Memorial Monument and Pavilion Beach are located nearby.

Breakfast included

Parking included

Luxury 1900's romantic retreat steps from the beach - King Suite!

Get rates

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

Kitchen

Washer

Comfort Inn & Suites Logan International Airport

85 American Legion Hwy, Revere, MA

Free cancellation

Reserve now, pay when you stay

CA $154

CA $180 total

includes taxes & fees

23 Mar - 24 Mar

Stay at this hotel in Revere. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Encore Boston Harbor and New England Aquarium are located nearby.

Pool

Breakfast included

SpringHill Suites by Marriott Boston Peabody

43 Newbury St./Route 1 North, Peabody, MA

Free cancellation

Reserve now, pay when you stay

CA $131

CA $146 total

includes taxes & fees

31 Mar - 1 Apr

Stay at this 3-star business-friendly hotel in Peabody. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Salem Witch Museum and MarketStreet Lynnfield are located nearby.

Pool

Hot tub

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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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Gloucester?

CA $658 is all you’ll need for a wonderful vacation in Gloucester. Bundle your flights and hotel into a Travelocity vacation package and see how much the savings start to pile up. With prices this good, you’ll want to start packing your suitcase now!

How long should my Gloucester vacation be?

Your Gloucester break can be as long as you like, but the majority of travelers stay about 2 nights. In the mood to hop off the beaten path and discover some less touristy sights? Lock in a couple more nights and experience a different side of this destination.

Where can I get the best vacation package deals for Gloucester?

Book your dream vacation with Travelocity. With access to 400 airlines and an impressive 1,000,000 hotels around the world, finding the perfect Gloucester package deal couldn’t be simpler.

Why should I purchase my Gloucester vacation bundle via Travelocity?

With fantastic service, 24/7 customer support and some of the most idyllic getaways on offer, you’ll never wander alone. And if you find a better price, we’ll match it. That’s our Price Match Guarantee.

Can I save on my Gloucester car rental if I book it with hotels and flights?

Bundling your hotel, flight and car into a Gloucester vacation package is a great way to score an amazing deal. Plus, having your own set of wheels gives you the freedom to get to all those famous sights you’re hoping to check out. Situated 72 kilometers from Gloucester, Plymouth Rock is one attraction that should be on your itinerary. Turn up the tunes and make a day trip of it.

Which airport is best for Gloucester?

There’s a good chance you’ll land at Logan Intl. Airport (BOS), which is 40 kilometers southwest of downtown Gloucester. Manchester-Boston Regional Airport (MHT) (72 kilometers away from central Gloucester) and Provincetown Municipal Airport (PVC) (72 kilometers away from central Gloucester) are other choices.

What is there to do in Gloucester?

While getting off the beaten track is rewarding, you shouldn’t ignore the big sights that make a place famous. Capt Bill & Sons Whale Watch and Pavilion Beach are just two of them in Gloucester.

Where should I stay when visiting Gloucester?

Many visitors choose to spend their nights at the Castle Manor Inn. It’s sure to be a great base for your Gloucester getaway.