Gloucester Vacations from $354

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Gloucester Vacation

Say goodbye to planning worries and hello to a Gloucester vacation package. With everything organized before you leave, you can focus on discovering the best of this city, starting with Great Neck, which is good for watersports, walking and nature. You'll want to go sightseeing during your trip to Gloucester. Swing by top attractions such as Wingaersheek Beach, Cape Ann and Good Harbor Beach. Stop daydreaming and start adventuring. Browse the multitude of options on Expedia today and put your Gloucester vacation plans into motion!

The Latest Gloucester Vacation Packages

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jun 1 - Jun 4
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
amazing staff and service, polite, friendly,

Reviewed on Apr 16, 2024

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Jul 8 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
8.2/10 Very Good! (1,617 reviews)
Great location - visited for Boston Marathon and it was perfect 👌

Reviewed on Apr 18, 2024

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
May 28 - Jun 2
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (2,192 reviews)
Out on a lim but cannot fault the hotel and the encore bud to get you near Boston central is good

Reviewed on Apr 17, 2024

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Jul 8 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
7.6/10 Good! (120 reviews)
The property is clean, the rooms are basic rooms, no clock, 2 pillows on a king bed. Very close to the T for transportation in to and out of Boston. Whole Foods is in within walking distance. It’s great for people looking for a place just out of Boston but not too far out of Boston.

Reviewed on Apr 19, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 8 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
9.2/10 Wonderful! (27 reviews)
Very good service. Furniture in all areas and the room is low and petite. Not comfortable. Bedding is comfortable. Food on Long Bar was well prepared. However presentation is pedestrian. Ordered Avacado Toast. Tasty, but arrived on a small plate. No garnish, no fruit etc. overall good stay.

Reviewed on Apr 8, 2024

Prices and availability subject to change. Additional terms may apply.

Gloucester Beach Vacation

There's nothing more enjoyable than a Gloucester vacation. Whether you're treating yourself to delicious cocktails at a local hot spot or flipping through a book along the water's edge, your trip to Gloucester is the perfect time to live out those beachy daydreams. Many like to stay close to Good Harbor Beach, situated just 2 miles (3 km) from downtown. However, you'll also discover plenty of Gloucester vacation packages close to Wingaersheek Beach and Niles Beach, two other superb nearby options.

Gloucester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
29,800
Max Temp Winter
35ºF
Max Temp Summer
70ºF
Top Sights
Wingaersheek Beach, Good Harbor Beach and Hammond Castle

Gloucester Hotel Deals

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is $211 per night from Apr 21 to Apr 22
$211
$236 total
includes taxes & fees
Apr 21 - Apr 22
9.6/10 Exceptional! (706 reviews)
"Lovely hotel. Very welcoming and friendly staff. Room with city view somewhat noisy early mornings(4am) due to loading docks across the street. Otherwise nice get away"

Reviewed on Apr 17, 2024

Beauport Hotel Gloucester
The Hotel at Cape Ann Marina
The Hotel at Cape Ann Marina
3.5 out of 5
75 Essex Avenue, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is $129 per night from Apr 21 to Apr 22
$129
$144 total
includes taxes & fees
Apr 21 - Apr 22
8.2/10 Very Good! (504 reviews)
"Love that the pool & hot tub are finally open. It's awesome at this time of the season that the Maine Scallop draggers are in at the marina fishing every day!"

Reviewed on Apr 18, 2024

The Hotel at Cape Ann Marina
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is $189 per night from Apr 28 to Apr 29
$189
$211 total
includes taxes & fees
Apr 28 - Apr 29
8/10 Very Good! (742 reviews)
"Womderful are and view accompanied by wonderful guest services and breakfast. Would highly reccomend."

Reviewed on Nov 27, 2023

Castle Manor Inn
See all 1,538 properties in Gloucester
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Gloucester vacation package cost?
Our Gloucester packages, which begin at just $354, are an awesome way to save money. Select your favorite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Gloucester?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got them all covered. Pick and choose a combination that suits your style and see your savings stack up. Of course, a package deal is never one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Gloucester getaway.
Where should I stay in Gloucester?
Stay where the action is. Many travelers like to book hotels within easy reach of top attractions, such as Wingaersheek Beach, Good Harbor Beach and Hammond Castle.
What are the top hotels in Gloucester?
Castle Manor Inn in the Annisquam neighborhood is an excellent choice for a Gloucester escape. Stay here and you’ll be in a perfect position to explore all that this happening city has to offer.
How far in advance should I book my Gloucester vacation?
To land rock-bottom prices, book nice and early. Air carriers typically release tickets, along with some of the lowest fares, nearly 12 months in advance. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway to Gloucester, there are always plenty of great deals on Expedia. Book something in today!
What does an Expedia Gloucester travel package include?
With Expedia, you can choose a combination of car rentals, flights and hotels to build your ideal Gloucester travel package. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Don’t forget — the more you bundle, the bigger the savings!
What should I know before booking a Gloucester travel package?
Tailor deals that match your budget with an Expedia package. Hotels, flights, rental cars — we’ve got them all. You’ll save precious dollars just for bundling your bookings. Whether you’re heading away on a winter adventure or drinking cocktails on a beach, your ideal getaway is only a few clicks away.
Can I choose my airline with a Gloucester Expedia vacation package?
With a vacation package, you’re the one in charge. Whether you’re looking to fly to Gloucester in coach or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Gloucester vacation package?
You can. We totally understand that life doesn’t always go to plan, so we’re happy to help if you need to make changes to your Gloucester vacation package. You may be able to cancel or change your itinerary at no cost if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Gloucester

Image for Wingaersheek Beach

Wingaersheek Beach

Offering fun in the sun, this coastal playground has calm water and everything you need for a day by the sea.

Wingaersheek Beach
Image for Good Harbor Beach

Good Harbor Beach

4.5/5(18 reviews)

With a reputation as Gloucester’s prettiest beach, this curve of white sand lapped by rolling waves sets the scene for soaking up the sun.

Good Harbor Beach
Image for Hammond Castle

Hammond Castle

4.5/5(8 reviews)

A medieval-style castle overlooking the blue ocean waters in Gloucester features a spellbinding collection of art, artifacts and quirky inventions.

Hammond Castle

What to do in Gloucester

Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

$30
Per adult
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Satanic Salem Walking Tour

Satanic Salem Walking Tour

$25
Per adult
100% of travellers recommend
Satanic Salem Walking Tour
Image for Wicked Awesome Tours: Witch Trial History and Salem Haunts!

Wicked Awesome Tours: Witch Trial History and Salem Haunts!

$25
Per adult
100% of travellers recommend
Wicked Awesome Tours: Witch Trial History and Salem Haunts!
See all activities in Gloucester

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.