How much does a Gloucester vacation package cost?

Offering great value package deals from CA $619 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 2025 from $300

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.

Lakeside Inn

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

7.4/10 Good! (2,171 reviews)

The grounds and the pool are amazing. The hotel and rooms are old and dated. Not bad for the price point if you just need a place to land at the end of the day.

Reviewed on Aug. 11, 2025

Boston Harbor Hotel

North End

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

9.8/10 Exceptional! (1,014 reviews)

The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on Aug. 11, 2025

Raffles Boston

Back Bay

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

9.6/10 Exceptional! (135 reviews)

Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug. 11, 2025

Boston Lodge and Suites

Dorchester

per person

Nov 1 - Nov 3

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.4/10 Very Good! (186 reviews)

Staypineapple, A Delightful Hotel, South End

South End

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

8.8/10 Excellent! (968 reviews)

This was the single greatest stay of my life. The hotel is so cute and beautiful with lovely pineapple decor on the pillows, ceiling, and everywhere else (the attention to detail is superb) they offer you a complimentary drink upon check in, they provide you with a free metal recyclable water bottle, and a very comfortable and soft robe. However, The most important moment of my trip was the incredible house keeping staff! I was there to get married and couldn’t get dressed and leave until 3:30. Not only did the staff stay later to clean my room before I brought my bride back after the wedding, but they decorated the entire room with a sequined bed runner, balloons, confetti, decorations, and more. Every member of the front desk staff were so amazing and kind and helpful every step of the way! Thank you all so much from the bottom of my heart on behalf of myself and my bride!! She was so excited to enter the room and have one last wedding day surprise! We will be back (exclusively!) to the Pineapple! 🍍

Reviewed on Aug. 10, 2025

Things to do in and around Gloucester

Gloucester, Massachusetts, offers a delightful mix of beach and outdoor activities, making it an ideal vacation spot. Enjoy scenic boat trips, indulge in golf vacations, or embark on shore excursions. For those who love shopping, there are plenty of excursions to explore. Don't miss the chance to relax on the beautiful beaches while taking in the local music concerts and educational experiences available throughout the area.

Shopping

For unique finds, visit Todd Farm Flea Market, about 20.9km from Gloucester, offering a vibrant local atmosphere. If you're up for a drive, MarketStreet Lynnfield, located 32.2km away, features a variety of shops and entertainment options, perfect for family outings.

Recreation

Enjoy a captivating concert at the Shalin Liu Performance Center, just 6.4km away, where the vibrant atmosphere enhances the musical experience. For relaxation, visit Halibut Point Reservation, 6.4km from Gloucester, offering serene landscapes perfect for unwinding. Don't miss a cultural evening at the Gorton Theatre, celebrating family and romance.

Adventure

Experience the thrill of marine life at Capt Bill & Sons Whale Watch, where you can witness majestic whales in their natural habitat. For a scenic hike, explore Dogtown's trails, surrounded by lush landscapes. A short drive away, enjoy family fun at the Water Park of New England, featuring various exhilarating attractions.

Nightlife

For an exciting nightlife experience in Gloucester, visit Park-9 Dog Bar, a lively drinking pub located 40.2km away. Enjoy the vibrant 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, offers a delightful vacation for beach lovers and outdoor enthusiasts alike. Explore its stunning beaches, historic houses, and fascinating museums that cater to those seeking cultural experiences and scenic beauty. Whether you're lounging by the shore or delving into local history, Gloucester is the perfect destination to unwind and enjoy the great outdoors.

Wingaersheek Beach: Experience the serene beauty of Wingaersheek Beach, known for its soft sands and tranquil waves. Ideal for sunbathing, swimming, or beachcombing, it offers a relaxing day by the water with stunning views of the coastline.
Cape Ann: Just 6.4km from Gloucester, Cape Ann boasts breathtaking scenery and charming beaches. Explore picturesque coastal towns, enjoy scenic drives, and take in the natural beauty that has inspired artists for generations.
Hammond Castle: Nestled in Gloucester, Hammond Castle exudes romance and history. Discover its medieval architecture, beautiful gardens, and captivating exhibits that reflect the culture and creativity of its founder, John Hammond.

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

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
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 $222

CA $248 total

Aug 14 - Aug 15

includes taxes & fees

8.2/10 Very Good! (1,011 reviews)

Nice spot

"Really pretty, comfy place. Good location."

Reviewed on Aug. 10, 2025

Beauport Hotel Gloucester

55 Commercial Street, Gloucester, MA

CA $474

CA $529 total

Sep 9 - Sep 10

includes taxes & fees

9.6/10 Exceptional! (871 reviews)

"Love the area for dining, shopping and relaxing."

Reviewed on Aug. 8, 2025

Ocean House Hotel at Bass Rocks

107 Atlantic Rd, Gloucester, MA

CA $341

CA $413 total

Sep 1 - Sep 2

includes taxes & fees

9/10 Wonderful! (727 reviews)

"Gorgeous views."

Reviewed on Jul. 22, 2025

See all 1,796 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.