Gloucester Vacation Packages 2026 from $539

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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.

The Latest Gloucester vacation packages

Price found within the past 48 hours. Click for updated prices.

Battery Wharf Hotel, Boston Waterfront

North End

Save 100% on your flight

$539

per person

Jan 2 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9/10 Wonderful! (2,041 reviews)

Reviewed on Oct 8, 2026

Boston Lodge and Suites

Dorchester

$639

per person

Nov 8 - Nov 12

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

The apt was tidy. Enough to sleep 8. Bathrooms were clean and updated. Parking can be difficult to find. It's about an hour from Salem.

Reviewed on Oct 4, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$839

per person

Jan 2 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$2,142

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

9.4/10 Exceptional! (487 reviews)

Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in. On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.

Reviewed on Oct 6, 2026

Raffles Boston

Back Bay

Save 100% on your flight

$1,256

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.6/10 Exceptional! (332 reviews)

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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

3 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.

A statue of a man with a wheel, surrounded by a stone base with an inscription, in a public square with houses and cars in the background.

Downtown Gloucester

2 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 Maritime 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.

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.

A lighthouse on a rocky shore with a wooden walkway leading to it.

Rocky Neck

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.

Stay near popular Gloucester attractions

A beach sign with footprints and a message to keep the beach clean.

Good Harbor Beach

9.2/10 (191 reviews)

Stroll along Good Harbor Beach's pristine white sands, walking to Salt Island at low tide. Reserve summer parking in advance to enjoy this Atlantic gem with its gentle surf and family-friendly atmosphere.

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A sandy beach with a row of houses in the background.

Wingaersheek Beach

9.4/10 (83 reviews)

This pristine beach captivates with white sands, clear shallow waters, and dramatic rock formations. Visit at low tide to explore expansive sandbars and discover hidden tide pools teeming with marine life.

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Hammond Castle

9.4/10 (86 reviews)

Explore this 1920s medieval-style castle built by inventor John Hays Hammond Jr. on Massachusetts' coast. Wander through grand halls filled with Roman and Renaissance artifacts while enjoying dramatic ocean views.

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A museum exhibit with a large wooden boat and a painting titled 'Out o' Gloucester'.

Cape Ann Museum

9.0/10 (23 reviews)

Step back in time to discover Gloucester’s history at a charming museum featuring fascinating artifacts, maritime artworks and a sculpture park.

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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)

Enjoy a day by the sea in a grassy Gloucester park that’s popular for festivals, farmers markets and concerts during summer.

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A beach with clear water, sandy shore, and green foliage.

Half Moon Beach

9.0/10 (45 reviews)

This crescent-shaped cove offers calm waters and golden sand within historic Stage Fort Park. Explore the rocky cliffs for picturesque views of Gloucester Harbor while enjoying the tranquil atmosphere.

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A bustling harbor with a red building, a maritime heritage center sign, and a crowd of people.

Maritime Gloucester

9.4/10 (63 reviews)

Maritime Gloucester showcases the oldest operating marine railway in the US alongside interactive exhibits of local marine life. Explore the historic Dory Shop or sail the harbor aboard the traditional Schooner Ardelle.

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Plum Cove Beach

8.0/10 (2 reviews)

If a restful vacation is part of your travel plans, Plum Cove 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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What to do in Gloucester

Salem, MA: History and Hauntings Guided Walking Tour

$40

per adult

90% of travellers recommend

Real Pirates Salem Museum General Admission Ticket

$22

per adult

84% of travellers recommend

Freedom Trail and Salem and The Witch Trail Self-Guided Walking Tour Bundle

Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle

$25

per traveler

100% of travellers recommend

See all activities in Gloucester

Gloucester Hotel Deals

Castle Manor Inn

141 Essex Avenue Gloucester MA

$229 nightly

$256 total

Oct 13 - Oct 14

Total with taxes and fees

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA

$249 nightly

$278 total

Nov 2 - Nov 3

Total with taxes and fees

Sea Lion Motel and Cottages

138 Eastern Avenue Gloucester MA

$173 nightly

$193 total

Oct 13 - Oct 14

Total with taxes and fees

9.2/10 Wonderful! (502 reviews)

"The room was excellent! Clean and comfortable. The staff was great,"

Reviewed on Oct 8, 2026

See all 1,872 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.

Find the Best Gloucester Vacation Packages

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.

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 0.2 miles from the city center 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.

Gloucester Essential Information

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

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Frequently asked questions

What's included in a Gloucester vacation package?

A Gloucester vacation package lets you combine round-trip flights, a hotel stay, and a rental car. As a beach destination, Gloucester offers many packages featuring hotels with easy access to the coast, and most package hotels in Gloucester offer ocean views. You'll typically fly into Boston Logan International Airport (BOS) for your trip.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Gloucester vacation package?

When you bundle, you can save up to 30%*. To save money on a Gloucester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for Gloucester?

For families, a Gloucester vacation package built around a stay at Beauport Hotel Gloucester offers a comfortable base. This 3.5-star property, rated 9.5 out of 10, features a game room and playground, making it easy for children to stay entertained, and travelers often praise the helpful staff and super clean rooms.Couples seeking a romantic Gloucester vacation package might consider a stay at The Hotel at Cape Ann Marina. This 3.5-star hotel, rated 8.3 out of 10, provides a bar/lounge and a hot tub for unwinding, with travelers noting the modern rooms and great location.Travelers looking for the best value vacation packages in Gloucester can find options like a package with a stay at The Vista. Rated 9.1 out of 10 and costing around $280 per night, this hotel offers free breakfast, a kitchenette, and an outdoor pool, with guests frequently highlighting the beautiful rooms and the pool as a huge plus.*Package availability and prices may change depending on dates and demand.

Is Gloucester better suited for a beach vacation or a cultural trip?

Gloucester is primarily a beach destination, making it ideal for travelers seeking coastal relaxation and water activities. Its shores feature popular spots like Wingaersheek Beach and Good Harbor Beach, perfect for enjoying the ocean.However, a Gloucester vacation also offers a rich cultural experience. The city is home to the historic Rocky Neck Art Colony, one of the oldest in the country, and the Cape Ann Museum which showcases local art and history. Travelers can also explore architectural gems like Hammond Castle.Therefore, a Gloucester vacation can easily combine beach days with explorations of its artistic and historical sites, offering a well-rounded trip.

Is Gloucester a good choice for a family vacation package?

Gloucester is a strong choice for family vacation packages, offering a mix of beach fun and family-friendly accommodations. The destination is known for its welcoming atmosphere and attractions suitable for all ages.For a comfortable family stay, Beauport Hotel Gloucester is a 3.5-star property rated 9.5 out of 10 by travelers. It features amenities like a playground and game room, making it easy for children to stay entertained, and travelers often praise its beautiful location and super clean rooms.Families can enjoy days out at Wingaersheek Beach, located about 3 miles from central Gloucester, known for its calm waters and tidal pools. Good Harbor Beach, also about 3 miles away, is another popular spot for family beach days.

What's included in a Gloucester beach vacation package?

Gloucester beach vacation packages typically bundle flights with a hotel stay, offering a convenient way to experience this coastal destination. Hotels like the 3.5-star Beauport Hotel Gloucester, rated 9.5 out of 10, about 3 miles from Wingaersheek Beach, provide amenities such as a restaurant and playground, and travelers often praise the beautiful location and exceptional food. The 4-star Ocean House Hotel at Bass Rocks, rated 8.9 out of 10 and about 4 miles from Wingaersheek Beach, features an outdoor pool, hot tub, and free breakfast, with travelers frequently saying they loved the rooms and great breakfast. Specific inclusions like meals, drinks, and water sports depend on the hotel and the rate you choose for your Gloucester vacation package.

Which Gloucester vacation packages include an ocean view?

Most Gloucester vacation packages include hotels with ocean views, as this destination is known for its coastal setting. The 3.5-star Beauport Hotel Gloucester, rated 9.5 out of 10 by travelers, is about 3 miles from Wingaersheek Beach and offers rooms with ocean views; travelers often highlight its beautiful location. Another option is Atlantis Oceanfront Inn, also rated 9.5 out of 10, about 4 miles from Wingaersheek Beach, where guests frequently praise the beautifully kept facilities and great breakfast. Keep in mind that specific ocean views depend on the room type and rate selected for your Gloucester vacation package.

What are the top things to do in Gloucester?

A Gloucester vacation offers a blend of beautiful beaches and rich cultural attractions:Browse and book things to do in Gloucester on Expedia.

Do you need to rent a car in Gloucester, or is public transport enough?

For a Gloucester vacation package, renting a car offers the most flexibility, especially if you plan to explore the various beaches and attractions spread across Cape Ann. While central Gloucester is walkable, many of the area's scenic spots and beaches, like Wingaersheek Beach (about 3 miles from the center) or Cape Ann (about 8 miles away), are best reached by car.Public transport options within Gloucester are limited, primarily focusing on local information and self-guided walks. For arrivals, Boston Logan International Airport (BOS) is the main gateway, located about 25 miles from central Gloucester, and a rental car or pre-arranged shuttle service would be practical for transfers. For Gloucester beach vacation packages, a car allows you to easily hop between different coastal areas and enjoy day trips.

Are Gloucester vacation package hotels conveniently located?

Gloucester vacation package hotels offer convenient access to both the city center and nearby coastal attractions. Many properties are situated within easy reach of central Gloucester, allowing travelers to explore downtown on foot.For example, Beauport Hotel Gloucester and The Highliner Hotel are both about a 5-minute walk from central Gloucester, placing guests close to shops and dining. Harborview Inn is also centrally located, about a 10-minute walk away. Other options like The Vista are about 1 mile from the center, offering a balance between town access and a slightly more secluded feel. This variety means you can choose a package that suits your preference for walkability or proximity to specific beaches.

Can I change or cancel my Gloucester vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Gloucester vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

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

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Gloucester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Gloucester?

To find last-minute vacation packages to Gloucester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Gloucester vacation packages?

Free cancellation on a Gloucester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Gloucester vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Gloucester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Gloucester vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

Gloucester Vacations from $539

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Gloucester Vacation

The Latest Gloucester vacation packages

Battery Wharf Hotel, Boston Waterfront

Boston Lodge and Suites

Boston Harbor Hotel

Four Seasons Hotel Boston

Raffles Boston

Where to stay in Gloucester

East Gloucester

Downtown Gloucester

Annisquam

Magnolia

Rocky Neck

Stay near popular Gloucester attractions

Good Harbor Beach

Wingaersheek Beach

Hammond Castle

Cape Ann Museum

Stage Fort Park

Half Moon Beach

Maritime Gloucester

Plum Cove Beach

What to do in Gloucester

Salem, MA: History and Hauntings Guided Walking Tour

Real Pirates Salem Museum General Admission Ticket

Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle

Gloucester Hotel Deals

Castle Manor Inn

Beauport Hotel Gloucester

Sea Lion Motel and Cottages

Find the Best Gloucester Vacation Packages

Things to do in and around Gloucester

Find the best attractions in and around Gloucester

Best time to go to Gloucester

Tips to save on your trip to Gloucester

Gloucester Beach Vacation

Things You Should Know About Gloucester

Gloucester Essential Information

More vacations you might like

Frequently asked questions

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