Book Exclusive Gloucester Vacation Packages

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Gloucester flight + hotel packages

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Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,371, price is now CA $811 per person
CA $811
per person
Oct 21 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
Price was CA $7,059, price is now CA $4,713 per person
CA $4,713
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 Mayo House are located nearby.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $2,154, price is now CA $1,469 per person
CA $1,469
per person
Oct 1 - Oct 4
found 9 hours 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,045, price is now CA $1,426 per person
CA $1,426
per person
Nov 11 - Nov 14
found 4 hours ago
Roundtrip flight included
Detroit (DTW) 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 Faneuil Hall Marketplace are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $2,159, price is now CA $1,547 per person
CA $1,547
per person
Nov 11 - Nov 14
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park 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 $236 per night
CA $236
CA $310 total
Sep 15 - Sep 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.
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is CA $455 per night
CA $455
CA $508 total
Sep 17 - Sep 18
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
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue Gloucester MA
The price is CA $240 per night
CA $240
CA $268 total
Sep 27 - Sep 28
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 Cape Ann are located nearby.
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd. Gloucester MA
The price is CA $315 per night
CA $315
CA $352 total
Aug 30 - Aug 31
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
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 $405 per night
CA $405
CA $486 total
Sep 27 - Sep 28
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 Cape Ann are located nearby.
Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd Gloucester MA
The price is CA $216 per night
CA $216
CA $512 total
Sep 2 - Sep 3
includes taxes & fees
Stay at this aparthotel in Gloucester. Enjoy free WiFi and free parking. Popular attractions Good Harbor Beach and Cape Ann are located nearby.
Kitchen
Parking included
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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 $811 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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