Gloucester Vacation Packages

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Your Gloucester Vacation

Say farewell to the worries of planning and hello to a Gloucester vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Great Neck, which is great for walking, nature and views. Eager to explore your new surroundings? Cape Ann, Good Harbor Beach and Wingaersheek Beach are just a few of the leading places to visit during a trip to Gloucester. No matter your travel plans or the size of your budget, organizing a tailored Gloucester vacation is a cinch with Expedia.

Top Gloucester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 12 - Aug. 16
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Your hotel is so stately and a grand dame. Everything is so elegant. Kudos to the staff and management.

Reviewed on May 25, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jun. 26 - Jun. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Perfect quintessential Boston charm! Wonderful and convenient location. Highly recommend!

Reviewed on May 26, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 12 - Aug. 16
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (31 reviews)
The door guys were fun and very helpful and that helped to make me feel more comfortable.

Reviewed on May 26, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 12 - Aug. 16
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Food was great, rooms were very comfortable and clean. Very pleasant stay.

Reviewed on May 26, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 8 - Aug. 12
found 13 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.2/10 Wonderful! (270 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

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 kilometres 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 Hotel Deals

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 CA $234 per night from May 28 to May 29
CA $234
CA $261 total
includes taxes & fees
May 28 - May 29
8.2/10 Very Good! (519 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 CA $354 per night from Jun. 3 to Jun. 4
CA $354
CA $396 total
includes taxes & fees
Jun 3 - Jun 4
9.6/10 Exceptional! (717 reviews)
"Everything was okay but no discount on price like senior or aarp discounts Staff was exceptional and very polite , food was good atmosphere very good rooms very quiet , I enjoyed my stay and plan on a return trip again soon."

Reviewed on May 24, 2024

Beauport Hotel Gloucester
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is CA $258 per night from May 28 to May 29
CA $258
CA $288 total
includes taxes & fees
May 28 - May 29
8.2/10 Very Good! (754 reviews)
"Room was clean, inn is beautiful, and customer service for arriving after hours was accommodating and easy. Definitely can recommend!"

Reviewed on May 26, 2024

Castle Manor Inn
See all 1,564 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Gloucester vacation package cost?
Our Gloucester packages, which begin at just CA $1,419, 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

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

CA $20
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

CA $23
Per adult
80% of travellers recommend
Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
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.