How much does a Gloucester vacation package cost?

Offering great value package deals from CA $897 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?

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. 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. 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. Bundle your accommodations and airfare: After you've settled on your trip dates and duration, lock in the ideal Gloucester vacation package for you.

Gloucester Vacation Packages & Trips 2026 from CA $897

Name: Beauport Hotel Gloucester
Price range: CA $597
Rating: 9.6

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.

Good Hotels Boston

South End

CA $897

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8/10 Very good! (55 reviews)

This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

North End

CA $1,829

per person

Aug 29 - Sep 2

found 11 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,001 reviews)

Couldn’t ask for a better place to stay while in Boston.

Reviewed on Jul 13, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

CA $6,763

per person

Aug 17 - Aug 24

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

10/10 Exceptional! (9 reviews)

It was an amazing relaxing place. Very family friendly

Reviewed on Jul 12, 2026

By the Sea Guests Bed & Breakfast & Suites

CA $939

per person

Aug 21 - Aug 24

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (195 reviews)

The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.

Reviewed on Jul 12, 2026

Four Seasons Hotel Boston

Bay Village

CA $2,553

per person

Sep 30 - Oct 3

found 9 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Boston (BOS)

9.4/10 Exceptional! (474 reviews)

perfecto

Reviewed on Jun 8, 2026

Things to do in and around Gloucester

Gloucester, Massachusetts, offers a delightful vacation experience with its stunning beaches and outdoor scenery. Visitors can enjoy various activities, including boat trips, golf vacations, and shore excursions. The local arts centre hosts music concerts, providing a vibrant cultural scene, while shopping excursions allow for unique finds. Whether you're looking to relax on the beach or explore the scenic beauty, Gloucester has something for everyone.

Shopping

In Gloucester, visit Oldies Marketplace for unique finds. If you're up for a drive, check out Todd Farm Flea Market for a lively atmosphere. MarketStreet Lynnfield offers a larger shopping experience with entertainment, family-friendly options, and a variety of stores, located a bit further away.

Recreation

Explore Waterfront Promenade Park for serene walks along the waterfront, perfect for relaxation. Enjoy live performances at the Shalin Liu Performance Center, where music fills the air. The Gorton Theatre offers captivating shows, creating a delightful cultural experience for families and couples alike.

Adventure

Experience thrilling water slides and lazy rivers at the Water Park of New England, located 25.7km from Gloucester. Enjoy exhilarating whale watching with Capt Bill & Sons, offering outdoor excitement. Explore scenic trails and breathtaking views while hiking Dogtown, right in Gloucester's beautiful surroundings.

Nightlife

For a lively evening in Gloucester, visit the Park-9 Dog Bar, a vibrant drinking pub located 40.2km away. Enjoy the entertainment and romantic vibes as you sip on your favourite beverage and soak in the friendly atmosphere with fellow patrons.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Gloucester

Gloucester, Massachusetts, is perfect for a beach and outdoor getaway, offering stunning scenery and rich culture. Visitors can explore beautiful beaches, historic houses, and fascinating museums, all of which provide a unique blend of relaxation and cultural experiences. Whether you're looking to soak up the sun or delve into local history, Gloucester has something for everyone to enjoy during their vacation.

Wingaersheek Beach: Enjoy the stunning views and serene atmosphere at Wingaersheek Beach, known for its soft sands and gentle waves, perfect for sunbathing and leisurely strolls along the shoreline. Experience the true essence of beach vibes in a picturesque setting.
Hammond Castle: Step into a world of romance and culture at Hammond Castle, an enchanting structure that blends medieval architecture with the scenic beauty of Gloucester. Explore its intriguing history and lovely gardens, making it a perfect spot for a romantic outing.
Salem Witch Museum: Located 20.9km from Gloucester, the Salem Witch Museum offers a captivating dive into the history and culture of the infamous witch trials. Engaging exhibits bring the past to life, making it a must-visit for history enthusiasts.

Best time to go to Gloucester

The best time to visit Gloucester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Gloucester falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Gloucester falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.1°F (-0.5°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	31.8°F (-0.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	36.7°F (2.6°C)	Light Rain	Mostly Sunny	Average	Average
April	45.1°F (7.3°C)	Light Rain	Mostly Sunny	Average	Average
May	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	62.4°F (16.9°C)	Light Rain	Mostly Sunny	Moderately High	Average
July	69.6°F (20.9°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
September	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	55.2°F (12.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	45.1°F (7.3°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	37.4°F (3.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low

Tips to save on your trip to Gloucester

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Gloucester.
Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Gloucester.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

141 Essex Avenue Gloucester MA

CA $247

CA $324 total

Jul 24 - Jul 25

includes taxes & fees

8.4/10 Very good! (1,019 reviews)

"The room was as pictured. The balcony had a nice view. Balcony chairs were worn. We did not pay for breakfast. We were in a side building"

Reviewed on Jul 13, 2026

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA

CA $597

CA $667 total

Aug 9 - Aug 10

includes taxes & fees

9.6/10 Exceptional! (979 reviews)

"Very clean room and wonderful beach view. Dining was extraordinary."

Reviewed on Jul 9, 2026

Atlantis Oceanfront Inn

125 Atlantic Road Gloucester MA

Fully refundableReserve now, pay when you stay

CA $582

CA $650 total

Jul 21 - Jul 22

includes taxes & fees

9.6/10 Exceptional! (484 reviews)

"Staff was excellent and helpful. Breakfast was amazing with a friendly host, waitress and waiter. Rooms were clean and cleaned daily."

Reviewed on Jun 30, 2026

See all 1,858 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.