Book Exclusive Gloucester Vacation Packages

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Gloucester flight + hotel packages

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The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Price was CA $1,720, price is now CA $1,099 per person
CA $1,099
per person
Mar 4 - Mar 11
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Wild Animal Lagoon and Bay View Street Beach are located nearby.
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
Price was CA $4,040, price is now CA $2,745 per person
CA $2,745
per person
Mar 4 - Mar 11
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Chatham Fish Pier are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,458, price is now CA $1,697 per person
CA $1,697
per person
Mar 18 - Mar 22
found 1 hour ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
Book a stay at this 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,579, price is now CA $2,588 per person
CA $2,588
per person
Apr 1 - Apr 6
found 11 hours ago
Roundtrip flight included
Ottawa (YOW) 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 Common are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,728, price is now CA $1,268 per person
CA $1,268
per person
Apr 3 - Apr 6
found 1 hour ago
Roundtrip flight included
Ottawa (YOW) 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
Get rates
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 Pavilion Beach and Fishermen's Memorial Monument 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
Free cancellation
Reserve now, pay when you stay
The price is CA $298 per night
CA $298
CA $333 total
Jan 11 - Jan 12
includes taxes & fees
Stay at this 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.
Parking included
Free WiFi
Luxury 1900's romantic retreat steps from the beach - King Suite!

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

Gloucester MA
Get rates
Stay at this cottage in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Plum Cove Beach and Halibut Point Reservation are located nearby.
Kitchen
Washer
Hawthorne Hotel

Hawthorne Hotel

3.5 out of 5
18 Washington Square W Salem MA
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this historic hotel in Salem. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.
Pet-friendly
Parking included
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
Free cancellation
Reserve now, pay when you stay
The price is CA $135 per night
CA $135
CA $151 total
Feb 6 - Feb 7
includes taxes & fees
Book a stay at this 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 Putnam House are located nearby.
Pool
Spa
Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

3 out of 5
999 Broadway Saugus MA
Free cancellation
The price is CA $126 per night
CA $126
CA $141 total
Jan 14 - Jan 15
includes taxes & fees
Book a stay at this business-friendly hotel in Saugus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Encore Boston Harbor and MarketStreet Lynnfield are located nearby.
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See all available properties in Gloucester
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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

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
Good Harbor Beach

Good Harbor Beach

Why not spend a carefree afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.

Good Harbor 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 $1,099 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

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