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.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
7/10 Good! (147 reviews)
Room had a really strong cigarette smell. Terrible. This is the 2nd time this happened at this property. Not sure i would come back again.

Reviewed on Jul. 27, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 22 - Sep 26
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (349 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul. 20, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Location was perfect.

Reviewed on Jul. 29, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on Jul. 28, 2025

Gloucester Beach Vacation

The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester vacation. If you're eager to save on your trip to Gloucester, we'll let you in on a secret — choose one of our Gloucester packages. Grab one close to Pavilion Beach, only 0.32 kilometres from the city centre and a must-do while here. Alternatively, select a package that puts you closer to Cressy Beach, another gorgeous coastline. Whichever you choose, you'll be left with extra dollars in your travel budget to have fun with.

Things You Should Know About Gloucester

  • Drift off to sleep to the gentle sounds of the sea in one of our Gloucester beach hotels. Nothing beats staying with walking distance of the ocean.
  • Private vacation homes are another top choice for people planning a vacation in Gloucester. Some great examples are Castle Manor Inn and The Hotel at Cape Ann Marina.
  • Roughly 29,800 people reside in Gloucester. If you want some tips about things to see and do here, why not start a conversation with some of the friendly locals? Our Gloucester things to do page is also a handy source of information.
  • Don't head home without exploring Cape Ann, Capt Bill & Sons Whale Watch and Dogtown. With the cash you save through our Gloucester vacation deals, you can see more impressive attractions like these.

Ready to book your vacation to Gloucester?

 

Choose your dates

Gloucester Hotel Deals

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is CA $222 per night from Aug 7 to Aug 8
CA $222
CA $248 total
Aug 7 - Aug 8
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Check in was easy, and friendly. The room was clean and looked like it went through some updating. The tv was small and the cable service was old school. It could definitely use some updating. It would be nice if the tiny refrigerator wasn’t on the floor. Our balcony had a nice view and the window ..."

Reviewed on Jul. 27, 2025

Castle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is CA $456 per night from Aug 25 to Aug 26
CA $456
CA $542 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (721 reviews)
"Gorgeous views."

Reviewed on Jul. 22, 2025

Ocean House Hotel at Bass Rocks
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
The price is CA $446 per night from Aug 25 to Aug 26
CA $446
CA $498 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (426 reviews)
"Oceanview"

Reviewed on Jul. 26, 2025

Atlantis Oceanfront Inn
See all 1,772 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

Discover the most popular places to visit in Gloucester

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
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
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

Mysteries & Murders of Salem Guided Night-Time Walking Tour

Mysteries and Murders of Salem Guided Night-Time Walking Tour

CA $48
per adult
92% of travellers recommend
Mysteries and Murders of Salem Guided Night-Time Walking Tour
"Wicked History Unveiled: Salem's Most Enigmatic Witch Tour"

Salem Ghosts: Witches, Warlocks, & Hauntings

CA $36
per adult
100% of travellers recommend
Salem Ghosts: Witches, Warlocks, & Hauntings
Salem: Haunted Footsteps Ghost Tour

Salem, Massachusetts: Haunted Footsteps Ghost Tour

CA $34
per adult
Salem, Massachusetts: Haunted Footsteps Ghost Tour
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from CA $972 on Expedia, you'll be pleasantly surprised at how much a vacation to Gloucester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Gloucester?
January, February and March are the best times to search for cheap Gloucester vacation packages. Travelling in quieter periods means you can usually find lower prices on hotels and flights.
How many days is enough for Gloucester?
You can visit all the major sights in Gloucester within a few days, including the popular Pebble Beach. If you want a longer Gloucester vacation, look at what sort of day tours and activities are available nearby.
Is it worth booking a vacation package to Gloucester?
Gloucester is a good vacation destination with attractions like Capt Bill & Sons Whale Watch among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Gloucester vacation promises a good time for everyone.
How to find the best Gloucester package deals?
Start your search for a Gloucester package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Gloucester package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Gloucester escape underway.
Is it cheaper to book a Gloucester vacation as a package?
You can enjoy significant savings on your Gloucester escape by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
How to plan a trip to Gloucester?

  1. Choose when to travel: Check your schedule and get packing. Your preferred season and the activities on offer will also help you decide when to escape to Gloucester.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Gloucester.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you'd like to get to in Gloucester. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your accommodations and airfare: After you've settled on your trip dates and duration, lock in the ideal Gloucester vacation package for you.

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