Gloucester Trips (flight + hotel)

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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 3 kilometers from downtown. However, you'll also discover plenty of Gloucester vacation packages close to Wingaersheek Beach and Niles Beach, two other superb nearby options.

Top hotels in Gloucester

The Hotel at Cape Ann Marina
The Hotel at Cape Ann Marina
3.5 out of 5
75 Essex Avenue, Gloucester, MA
Fully refundable
The price is P7,418 per night from 28 Apr to 29 Apr
P7,418
per night
28 Apr - 29 Apr
8.2/10 Very Good! (507 reviews)
"The staff are very professional, kind, pleasant, and a wealth of knowledge navigating Gloucester. This was our first time here at Cape Ann Marina Hotel and we enjoyed every minute of our stay. From having drinks with Bartender Megan to meeting new friends during the tasty continental breakfast. We ..."

Reviewed on Apr 18, 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 P11,960 per night from 29 Apr to 30 Apr
P11,960
per night
29 Apr - 30 Apr
9.6/10 Exceptional! (708 reviews)
"Beautiful resort with friendly staff. Can’t wait to visit again."

Reviewed on Apr 21, 2024

Beauport Hotel Gloucester
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is P10,868 per night from 28 Apr to 29 Apr
P10,868
per night
28 Apr - 29 Apr
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 1,540 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.

Popular places to visit

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

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

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

What to do in Gloucester

Image for Cape Ann Harbor Tour: Self-Guided Drive

Cape Ann Harbor Tour: Self-Guided Drive

P846
Per adult
100% of travellers recommend
Cape Ann Harbor Tour: Self-Guided Drive
Image for Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport

Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport

P846
Per adult
80% of travellers recommend
Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport
Image for Ultimate Boston Audio Tour Bundle

Ultimate Boston Audio Tour Bundle

P1,244
Per adult
Ultimate Boston Audio Tour Bundle
See all activities in Gloucester

More trip options

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