Gloucester Trips (flight + hotel)

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to P 3,118 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 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

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is P12,975 per night from 3 Nov to 4 Nov
P12,975
P14,493 total
includes taxes & fees
Nov 3 - Nov 4
9.6/10 Exceptional! (777 reviews)
"I loved the roof top hot tub and pool!"

Reviewed on Oct 25, 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 P8,148 per night from 2 Dec to 3 Dec
P8,148
P9,101 total
includes taxes & fees
Dec 2 - Dec 3
8.2/10 Very Good! (658 reviews)
"Junior suite was beautiful, recently remodeled and done right! It felt very high end and was easily the cleanest hotel I've ever stayed at"

Reviewed on Nov 2, 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 P11,039 per night from 10 Nov to 11 Nov
P11,039
P12,331 total
includes taxes & fees
Nov 10 - Nov 11
8.2/10 Very Good! (938 reviews)
"Cozy and very clean"

Reviewed on Nov 1, 2024

Castle Manor Inn
See all 1,635 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

What to do in Gloucester

Image for Whale Watching Tour in Gloucester

Whale Watching Tour in Gloucester

P2,737
Per adult
98% of travellers recommend
Whale Watching Tour in Gloucester
Image for Cape Ann Harbor Tour: Self-Guided Drive

Cape Ann Harbor Tour: Self-Guided Drive

P969
Per adult
100% of travellers recommend
Cape Ann Harbor Tour: Self-Guided Drive
Image for Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

P969
Per adult
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
See all activities in Gloucester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.