Book Exclusive Gloucester Vacation Packages

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Gloucester flight + hotel packages

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

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,383, price is now CA $1,403 per person
CA $1,403
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Book a stay at this 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 Harbor are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,800, price is now CA $1,641 per person
CA $1,641
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $3,340, price is now CA $2,002 per person
CA $2,002
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Stay at this 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 Boston Common and TD Garden are located nearby.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $2,986, price is now CA $1,997 per person
CA $1,997
per person
Sep 23 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $2,092, price is now CA $1,416 per person
CA $1,416
per person
Oct 1 - Oct 4
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
Book a stay at this luxury apartment in Everett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

Top Gloucester hotels deals

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
The price is CA $253 per night
CA $253
CA $331 total
Jul 15 - Jul 16
includes taxes & fees
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 Wingaersheek Beach and Good Harbor Beach are located nearby.
Parking included
Free WiFi
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is CA $577 per night
CA $577
CA $644 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this 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 Good Harbor Beach and Wingaersheek Beach are located nearby.
Free WiFi
Restaurant
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road Gloucester MA
Free cancellation
Reserve now, pay when you stay
The price is CA $582 per night
CA $582
CA $650 total
Jul 19 - Jul 20
includes taxes & fees
Stay at this motel 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 Hammond Castle are located nearby.
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd Gloucester MA
Free cancellation
Reserve now, pay when you stay
The price is CA $531 per night
CA $531
CA $628 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this 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 Wingaersheek Beach are located nearby.
Pool
Hot tub
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue Gloucester MA
The price is CA $294 per night
CA $294
CA $329 total
Jul 14 - Jul 15
includes taxes & fees
Book a stay at this business-friendly motel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Good Harbor Beach and Wingaersheek Beach are located nearby.
Pool
Breakfast included
Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd Gloucester MA
The price is CA $294 per night
CA $294
CA $605 total
Jul 14 - Jul 15
includes taxes & fees
Stay at this aparthotel in Gloucester. Enjoy free WiFi and free parking. Popular attractions Good Harbor Beach and Wingaersheek Beach are located nearby.
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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.

Stay near popular Gloucester attractions

A rocky shoreline with large boulders and calm water.

Wingaersheek Beach

9.4/10 (83 reviews)
Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.
See properties

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 $1,403 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

A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.
A beach with clear water, sandy shore, and green foliage.
A group of people in naval uniforms on a wooden deck, with a ship's rigging and a clear blue sky in the background.
A historic building labeled "MANUFACTURY" with a large chimney, a dock with fishing boats, and a sunset sky.
A coastal town with houses on a cliff overlooking the sea.

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