How much does a Gloucester vacation package cost?

Offering great value package deals from $318 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?

If you'd like to snag a cheap Gloucester vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on accommodations and flights during these months — perfect for travelers wishing to save money.

How many days is enough for Gloucester?

Typically, a few days is enough for a Gloucester vacation. With a detailed itinerary, you can go to all the top attractions including Hammond Castle , as well as explore some hidden gems along the way.

Is it worth booking a vacation package to Gloucester?

Gloucester offers everything you need for an amazing escape. Get your Gloucester vacation off to a flying start by visiting popular attractions like Wingaersheek Beach .

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?

Choose when to get away: Check your diary and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to visit Gloucester. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Gloucester. Use Expedia's trip planning tool to explore Gloucester: Research every aspect of your trip to Gloucester with this handy planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Gloucester. Then, estimate how long you'll need for each, including any travel time. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Gloucester vacation package that brings all your bookings together. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Gloucester's best offerings. Find all the incredible things to do in Gloucester with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Gloucester vacation packages?

If you're like us, you love exploring new places but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Gloucester trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

Top Gloucester Vacation Packages 2026 - Book Now

Things to do in and around Gloucester

Gloucester, Massachusetts, is a fantastic destination for beach lovers and outdoor enthusiasts alike. Visitors can enjoy a variety of activities including music concerts, exploring local arts centers, and engaging in educational experiences. Outdoor activities such as bird watching and audio tours provide opportunities to discover the scenic beauty of Gloucester and its rich history. Whether you're relaxing on the beach or exploring the vibrant local culture, Gloucester has something for everyone.

Shopping

In Gloucester, visit local shops and boutiques for unique gifts. For a broader selection, if you're up for a drive, check out Todd Farm Flea Market and Bewitched in Salem, both 13 miles away, or head to MarketStreet Lynnfield, 20 miles away, for entertainment and family-friendly shopping.

Recreation

Experience the Shalin Liu Performance Center for captivating music concerts that uplift your spirit. At North Shore Music Theatre, immerse yourself in cultural performances perfect for a romantic night out. For tranquility, stroll along the Waterfront Promenade Park, where you can unwind and enjoy nature's beauty.

Adventure

Experience the thrill of whale watching with Capt Bill & Sons Whale Watch in Gloucester, where you can encounter majestic marine life. Hike the scenic trails of Dogtown for breathtaking views and natural beauty. For family fun, visit the Water Park of New England, located 16 miles from Gloucester.

Nightlife

Gloucester's nightlife offers a unique charm, highlighted by the Park-9 Dog Bar, a vibrant drinking pub 25 miles away. Enjoy a lively atmosphere filled with entertainment and romance vibes, perfect for unwinding after a day of exploration.

*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 a perfect destination for beach lovers and outdoor enthusiasts, offering stunning coastal scenery and a rich cultural experience. Explore beautiful beaches, historic homes, and interesting museums that cater to diverse interests. Whether you're looking for a relaxing beach vacation or eager to discover the local culture, Gloucester has something for everyone to enjoy.

Wingaersheek Beach: Enjoy the serene beauty of Wingaersheek Beach, where soft sands meet gentle waves. This picturesque beach is perfect for sunbathing, swimming, and beachcombing, offering a relaxing atmosphere for visitors of all ages.
Cape Ann: Just 4 miles from Gloucester, Cape Ann boasts stunning coastal scenery with breathtaking views. Explore its charming beaches and rugged cliffs, making it an ideal spot for hiking, photography, and enjoying the great outdoors.
Hammond Castle: Nestled in Gloucester, Hammond Castle offers a romantic glimpse into the past with its medieval architecture and rich cultural history. Wander through the beautiful gardens and explore the fascinating exhibits that celebrate art and innovation.

Best time to go to Gloucester

The best time to visit Gloucester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 to Gloucester during the low season (December to February) for more affordable options.
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.

Language	English
Currency	U.S dollars
Closest Airport	Logan Intl. Airport (BOS)
Population	29,800
Max Temp Winter	35ºF
Max Temp Summer	70ºF
Top Sights	Wingaersheek Beach, Good Harbor Beach and Hammond Castle

Gloucester Vacations from $318

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