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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
per person
Apr. 9 - Apr. 12
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
This lil apartment is located across street from Walgreens and Dollar Tree so was very convenient for the little things we forgot to pack. Safe surroundings. Parking is a lil tricky, but be patient and just drive round the block you will easily find something. Walking distance to the train station. Host was very sweet and helped us with all our needs. Only a few minor issues. The floors and doors are very squeaky, but it is an older home so that is expected we just hope we didn't bother those below us. Our heat did not work and we did need it a couple of nights that were pretty cold, but we told the host and she was gonna have HVAC to come out after we left. Weather was crazy cold one day and got the next so it would have been nice to have some a/c but after thinking about it, I'm sure not many places up north have a/c like we do in the south 😁...all in a lol a great place to stay, easy travel to Salem as well by train. Would stay again at this property.

Reviewed on Oct. 25, 2024

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
Apr. 4 - Apr. 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.8/10 Excellent! (1,001 reviews)
Absolutely beautiful hotel. I had a medical emergency and they helped me in the middle of the night. Really appreciate all of their hard work.

Reviewed on Jan. 21, 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Apr. 5 - Apr. 12
found 15 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
7.2/10 Good! (494 reviews)
Helen was very helpful

Reviewed on Jan. 5, 2025

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Apr. 5 - Apr. 12
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
7/10 Good! (124 reviews)
This was the perfect stay for what we needed. It was what we expected. The pictures are very accurate. Highly recommend the garage parking. Easy access to room from garage. The T is super close which makes travel around the city super convenient. Would stay at the same location again but would try to request a room with a view of the harbor/city.

Reviewed on Jan. 21, 2025

The Beverly

The Beverly

3 out of 5
Save 100% on your flight
per person
Apr. 5 - Apr. 12
found 15 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
8.4/10 Very Good! (263 reviews)
Suite was nice. WiFi is basically non existent.

Reviewed on Dec. 8, 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.

Ready to book your vacation to Gloucester?

 

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Gloucester Hotel Deals

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is CA $273 per night from Feb. 2 to Feb. 3
CA $273
CA $305 total
includes taxes & fees
Feb 2 - Feb 3
9.4/10 Exceptional! (591 reviews)
"Incredibly relaxing, loved my stay here."

Reviewed on May 3, 2023

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
8.2/10 Very Good! (663 reviews)
"Front desk ladies were wonderful!"

Reviewed on Jan. 1, 2025

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The Hotel at Cape Ann Marina
The Vista
The Vista
2.5 out of 5
22 Thatcher Rd., Gloucester, MA
9.2/10 Wonderful! (361 reviews)
Great place
"Great relaxing place to stay with amazing views. And lovely kind staff."

Reviewed on Nov. 19, 2024

Get rates
The Vista
See all 1,643 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?
Offering great value package deals from CA $856 on Expedia, you’ll be thrilled with how little a vacation to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
You’re likely to find lower rates and greater availability in January, February and March. Explore our cheap Gloucester vacation packages and you could score some excellent off-season deals.
How many days is enough for Gloucester?
Typically, a few days is great for a Gloucester vacation. With a well-organized schedule, you can check out all the best sights such as Cressy Beach, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester vacation on a high note by exploring major attractions like Capt Bill & Sons Whale Watch.
How to find the best Gloucester package deals?
Use Expedia’s filters to find some great Gloucester package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or look for Gloucester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it’s usually best to book your vacation package as soon as possible.
Is it cheaper to book a Gloucester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You’ll typically get a better deal than booking each component separately. And you’ll still have the freedom to create a tailored Gloucester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Gloucester?
If you’re considering a spontaneous Gloucester getaway, check out our last-minute deals that can be booked up to a week before you go. Don’t want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Gloucester?

  1. Choose your dates: What you’d like to do in Gloucester and your favorite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your hotel, you’ll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Gloucester.
  3. Decide how long to go away for: Now that you’re up to speed on Gloucester, you can figure out the perfect length of your break. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: Once you’ve nailed down your travel dates and duration, lock in the right Gloucester vacation package for you.

Discover the most popular places to visit in Gloucester

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
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
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

Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts Self-Guided Driving and Walking Tours Bundle

CA $72
per adult
Massachusetts Self-Guided Driving and Walking Tours Bundle
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $22
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Ultimate Boston Self-Guided Bundle Audio Tour

Ultimate Boston Self-Guided Audio Tour Bundle

CA $36
per adult
Ultimate Boston Self-Guided Audio Tour Bundle
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.