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.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $1,913, price is now CA $1,260 per person
CA $1,260
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,093, price is now CA $1,369 per person
CA $1,369
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Price was CA $3,422, price is now CA $2,353 per person
CA $2,353
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Price was CA $2,556, price is now CA $1,779 per person
CA $1,779
per person
Aug 24 - Aug 31
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,863, price is now CA $2,033 per person
CA $2,033
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common 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 $252 per night
CA $252
CA $328 total
Jul 16 - Jul 17
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 $573 per night
CA $573
CA $640 total
Aug 2 - Aug 3
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
The price is CA $578 per night
CA $578
CA $645 total
Jul 21 - Jul 22
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.
Pool
Parking included
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd Gloucester MA
The price is CA $477 per night
CA $477
CA $567 total
Jul 26 - Jul 27
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 $292 per night
CA $292
CA $327 total
Jul 21 - Jul 22
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
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd. Gloucester MA
The price is CA $445 per night
CA $445
CA $497 total
Jul 21 - Jul 22
includes taxes & fees
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 Cape Ann are located nearby.
Pool
Breakfast included
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.

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 $1,260 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.

Explore More Ways to Travel with Travelocity