Gloucester Vacation Packages
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Top Gloucester vacation deals
- Boston Lodge and Suites
Sept 7 - Sept 9Boston Lodge and Suites + Flight
Dorchester2 nights4.0 star property8.4/10 - Very good (190 reviews)"Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles."Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Boston (BOS)YYZ - BOS • Nonstop BOS - YYZ • 1 stopCA $1,210CA $657found 16 hours agoper traveller - Boston Harbor Hotel
Sept 4 - Sept 7Boston Harbor Hotel + Flight
North End3 nights5.0 star property9.8/10 - Exceptional (1,002 reviews)"A fantastic stay. The room was so comfortable and cleaned carefully every day. Room overlooked the harbor and the activity of boats but it was peaceful and calm. We LOVED our stay and definitely will return when we’re back in Bean Town!"Reviewed July 30, 2026Roundtrip • Hamilton (YHM) - Boston (BOS)YHM - BOS • 1 stop BOS - YHM • 1 stopCA $2,396CA $1,474found 21 hours agoper traveller - The Charles Hotel
Sept 23 - Sept 27The Charles Hotel + Flight
West Cambridge4 nights5.0 star property9.4/10 - Exceptional (1,003 reviews)Roundtrip • Toronto (YTO) - Boston (BOS)YTZ - BOS • Nonstop BOS - YTZ • NonstopCA $2,044CA $1,395found 1 day agoper traveller - The Langham, Boston
Oct 1 - Oct 4The Langham, Boston + Flight
Downtown Boston3 nights5.0 star property9.6/10 - Exceptional (1,000 reviews)Roundtrip • Toronto (YTO) - Boston (BOS)YTZ - BOS • Nonstop BOS - YYZ • NonstopCA $2,466CA $1,683found 1 day agoper traveller - Four Seasons Hotel Boston
Sept 4 - Sept 7Four Seasons Hotel Boston + Flight
Bay Village3 nights5.0 star property9.4/10 - Exceptional (475 reviews)"Amazing hotel Amazing facility and Amazing team. Clean excellent location and very friendly"Reviewed July 30, 2026Roundtrip • Hamilton (YHM) - Boston (BOS)YHM - BOS • 1 stop BOS - YHM • 1 stopCA $2,826CA $1,935found 1 day agoper traveller
Where to stay in Gloucester
East Gloucester
Downtown Gloucester
Annisquam
Rocky Neck
Magnolia
Discover the most popular places to visit in Gloucester
What to do in Gloucester
Wicked Awesome Tours: Witch Trial History and Salem Haunts!
History and Hauntings of Salem Guided Walking Tour
Real Pirates Salem Museum General Admission Ticket
Gloucester Hotel Deals
Ocean House Hotel at Bass Rocks
Ocean House Hotel at Bass Rocks
Frequently Asked Questions
How much does a Gloucester vacation package cost?
Offering great value package deals from CA $657 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.
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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.
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.
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.