Gloucester Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to ₩9,995 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

Gloucester Hotel Deals

Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is ₩256,125 per night from Jun 2 to Jun 3
₩256,125
per night
Jun 2 - Jun 3
8/10 Very Good! (745 reviews)
"Quiet clean and close to marina"

Reviewed on May 10, 2024

Castle Manor Inn
The Hotel at Cape Ann Marina
The Hotel at Cape Ann Marina
3.5 out of 5
75 Essex Avenue, Gloucester, MA
The price is ₩269,677 per night from May 23 to May 24
₩269,677
per night
May 23 - May 24
8.2/10 Very Good! (518 reviews)
"The room was dated, but the rooms are being remodeled. It was clean, had easy access and had a beautiful view!"

Reviewed on May 10, 2024

The Hotel at Cape Ann Marina
Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is ₩371,314 per night from Jun 3 to Jun 4
₩371,314
per night
Jun 3 - Jun 4
9.6/10 Exceptional! (714 reviews)
"The Beauport is a beautiful hotel, with a roof top deck and pool, and lovely ocean views. The staff is friendly and very willing to help with anything and everything. The bed was very comfortable and both the bedroom and bathroom were immaculately clean. Top notch hotel in every respect."

Reviewed on May 18, 2024

Beauport Hotel Gloucester
See all 1,548 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.

Frequently asked questions

How much does a Gloucester vacation package cost?
Our Gloucester packages, which begin at just , 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

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
Image for Good Harbor Beach

Good Harbor Beach

4.5/5(18 reviews)

If a restful vacation is part of your travel plans, Good Harbor Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

Good Harbor Beach
Image for Hammond Castle

Hammond Castle

4.5/5(8 reviews)

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

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.