Book Exclusive Gloucester Vacation Packages

Choose one or more items to build your trip:

Gloucester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Feb. 14 - Feb. 17
found 13 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Feb. 14 - Feb. 17
found 13 hours ago
Roundtrip flight included
Buffalo (BUF) 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 Boston Common are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Feb. 15 - Feb. 18
found 13 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Feb. 6 - Feb. 9
found 10 hours 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.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Feb. 14 - Feb. 17
found 13 hours ago
Roundtrip flight included
Buffalo (BUF) 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 New England Aquarium and Boston Common are located nearby.

Top Gloucester hotels deals

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is CA $292 per night
CA $292
CA $326 total
includes taxes & fees
13 Jan - 14 Jan 2025
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.
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
Get rates
Stay at this 3.5-star hotel in Gloucester. Enjoy free parking, a marina, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Stage Fort Park and Fishermen's Memorial Monument are located nearby.
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
Get rates
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.
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
Get rates
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.
Beach Life Bliss - steps to the beach

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 Plum Cove Beach and Paper House are located nearby.
Ashworth by the Sea

Ashworth by the Sea

3 out of 5
295 Ocean Blvd, Hampton, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $147 per night
CA $147
CA $160 total
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star beach hotel in Hampton. Enjoy 3 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Hampton Beach and Casino Cascade Water Slide are located nearby.
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

Good Harbor Beach

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.

Good Harbor Beach
Wingaersheek Beach

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.

Wingaersheek Beach
Hammond Castle

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.

Hammond Castle

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 $873 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.

Photos of local treasures

Browse Gloucester vacation photos for more inspiration

Gloucester
Gloucester
Gloucester
Gloucester
Gloucester