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

Dorchester
CA $755
per person
Oct 21 - Oct 23
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 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 on May 19, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
CA $1,625
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,011 reviews)
A bit dated, but beautiful situated and appointed. Little ways from everything.

Reviewed on Aug 28, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

CA $1,268
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (7 reviews)
Raffles Boston

Raffles Boston

Back Bay
CA $1,636
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (305 reviews)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
CA $1,610
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (1,325 reviews)

Where to stay in Gloucester

Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Gloucester
A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

East Gloucester

2 out of top 10 points of interest in this area

If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.

Find hotels in East Gloucester
Gloucester MA Fishermens Memorial

Downtown Gloucester

3 out of top 10 points of interest in this area

While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch.

Find hotels in Downtown Gloucester
A coastal landscape with a lighthouse, rocky shoreline, and a beach.

Annisquam

While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach.

Find hotels in Annisquam
Annisquam lighthouse in Massachusetts

Rocky Neck

1 out of top 10 points of interest in this area

While Rocky Neck might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Rocky Neck Art Colony and Maritime Gloucester.

Find hotels in Rocky Neck
A garden with purple flowers and a foggy coastline.

Magnolia

Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.

Find hotels in Magnolia

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.1°F (-0.5°C)Light RainMostly SunnyModerately LowSlightly Low
February31.8°F (-0.1°C)Light RainMostly SunnyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly SunnyAverageAverage
April45.1°F (7.3°C)Light RainMostly SunnyAverageAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageSlightly High
June62.4°F (16.9°C)Light RainMostly SunnyModerately HighAverage
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighAverage
August69.4°F (20.8°C)Light RainMostly SunnyModerately HighAverage
September64.0°F (17.8°C)Light RainMostly SunnyAverageSlightly High
October55.2°F (12.9°C)Light RainMostly SunnyAverageSlightly High
November45.1°F (7.3°C)Light RainMostly SunnyModerately LowAverage
December37.4°F (3.0°C)Light RainMostly SunnyModerately LowSlightly 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

Castle Manor Inn

141 Essex Avenue Gloucester MA
CA $236
CA $310 total
Sep 15 - Sep 16
includes taxes & fees
Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
CA $454
CA $507 total
Sep 17 - Sep 18
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"Beautiful spot right on the ocean. Loved the rooftop bar."

Reviewed on Aug 29, 2026

Beauport Hotel Gloucester
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

138 Eastern Avenue Gloucester MA
CA $229
CA $256 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (479 reviews)
"Staff was most helpful. Our room was near a busy road, so we heard cars at night. Very basic, but comfortable room. Bedding was excellent. Walk to Good Harbor is doable, but walk back up the hill could be tough if you have a lot to carry."

Reviewed on Aug 25, 2026

Sea Lion Motel and Cottages
See all 1,890 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.
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Stay near popular Gloucester attractions

A rocky shoreline with large boulders and calm water.

Wingaersheek Beach

9.4/10 (83 reviews)
Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.
See properties
A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Good Harbor Beach

9.2/10 (191 reviews)
Why not spend a carefree afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.
See properties
A stone archway with a view of the sea.

Hammond Castle

9.4/10 (86 reviews)
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.
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An art gallery with wooden flooring and paintings on the walls.

Cape Ann Museum

9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
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A coastal town with rocky shores, a prominent church, and a clear blue sky.

Stage Fort Park

9.2/10 (71 reviews)
After visiting Stage Fort Park, make a plan to see the other sights and activities in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
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A beach with clear water, sandy shore, and green foliage.

Half Moon Beach

9.0/10 (45 reviews)
If a restful vacation is part of your travel plans, Half Moon Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.
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A coastal scene with clear blue water, rocky shoreline, and several sailboats anchored in the distance.

Niles Beach

8.0/10 (8 reviews)
Why not spend a carefree afternoon at Niles Beach during your travels in Gloucester? Make some time to visit the shops while you're in the area.
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A group of people in naval uniforms on a wooden deck, with a ship's rigging and a clear blue sky in the background.

Maritime Gloucester

9.4/10 (63 reviews)
You can spend an afternoon studying the exhibits at Maritime Gloucester during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
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What to do in Gloucester

Salem, MA: History and Hauntings Guided Walking Tour

Salem, MA: History and Hauntings Guided Walking Tour

CA $50
per adult
88% of travellers recommend
Salem, MA: History and Hauntings Guided Walking Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

CA $51
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

CA $30
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from CA $755 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.