Gloucester Holidays

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Gloucester Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

Sunset Park
S$801
per person
9 Oct - 12 Oct
found 5 hours ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
6.4/10 (1,000 reviews)
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

S$1,008
per person
9 Oct - 12 Oct
found 5 hours ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
8.8/10 Excellent! (1,778 reviews)
HomeAwhile

HomeAwhile

S$991
per person
9 Oct - 12 Oct
found 5 hours ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
9.4/10 Exceptional! (180 reviews)
There was hair in the bed, got new sheets and they had hair as well. The comforter was dirty.

Reviewed on 6 Aug, 2026

LivAway Suites Portland-Scarborough

LivAway Suites Portland-Scarborough

S$878
per person
9 Oct - 12 Oct
found 5 hours ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
8/10 Very good! (301 reviews)
Good bed, however missing pots and pans and other appliances that one would use with the full kitchen that was given

Reviewed on 6 Aug, 2026

Candlewood Suites Portland - Scarborough by IHG

Candlewood Suites Portland - Scarborough by IHG

S$874
per person
9 Oct - 12 Oct
found 5 hours ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
8.2/10 Very good! (1,001 reviews)
Outside trash bins over flowing, cigarette butts all over ground, dog feces not cleaned up, sidewalk and gazebo area with lose rock where cement had deteriorated. Not a great visual first impression and not addressed quickly. Nice that rooms have some cookware dishes etc, but would sure be nice to have a small knife to cut instead the big one, Some kitchen shears maybe on a chain screwed into the wall if worried about theft. More information on what is available to purchase or to borrow as those were great, but I did not happen on some of it until I had stayed several days or already purchased items. Would have been nice to be able to purchase some items in small quantity such as a baggie with 3 or 4 packets of catsup, mustard, mayonnaise, salt, pepper and small tubs of peanut butter and jelly. small containers of cooking oil. more than one kind of laundry detergent (some for sensitive skin) dryer sheets. I hated that I ended up throwing away lots of food items due to not being able to buy small enough amounts for my needs from the grocery store.

Reviewed on 4 Aug, 2026

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.

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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.

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A coastal landscape with a lighthouse, rocky shoreline, and a beach.

Annisquam

Though Annisquam may not have many top sights, you can venture to the surrounding area to see attractions like Wingaersheek Beach and Plum Cove Beach.

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Annisquam lighthouse in Massachusetts

Rocky Neck

While visiting Rocky Neck, you might make a stop by sights like Rocky Neck Art Colony and Bryan Gallery.

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A garden with purple flowers and a foggy coastline.

Magnolia

You'll enjoy the beaches and restaurants in Magnolia. You might want to make time for a stop at Gray Beach or Massachusetts Bay.

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Things to do in and around Gloucester

Gloucester offers a delightful blend of beach and outdoor activities, making it an ideal destination for a scenic getaway. Visitors can enjoy music concerts, explore local arts centres, and participate in educational experiences. Weekend getaways can be enhanced with walking tours, exciting adventures, and a plethora of attractions, alongside seasonal activities that cater to diverse interests.

Shopping

For unique gifts, visit Bewitched in Salem, 20.9km from Gloucester. You can also explore Todd Farm Flea Market, a lively spot for various treasures, also 20.9km away. If you're up for a drive, MarketStreet Lynnfield, 32.2km from Gloucester, offers a vibrant shopping experience with entertainment options.

Recreation

Immerse yourself in soothing melodies at the Shalin Liu Performance Center, just 6.4km from Gloucester. Enjoy captivating performances at the Gorton Theatre, perfect for a romantic evening. For relaxation, explore the serene Halibut Point Reservation, where nature rejuvenates the spirit and fosters wellness.

Adventure

Embark on an exhilarating adventure with Capt Bill & Sons Whale Watch, where you can marvel at magnificent whales in their natural habitat. For a scenic hike, explore Dogtown’s picturesque trails surrounded by lush landscapes. For family fun, visit the Water Park of New England, a short drive from Gloucester.

Nightlife

Gloucester's nightlife offers a relaxed yet vibrant atmosphere. Visit Park-9 Dog Bar, a charming drinking pub 40.2km away, where you can unwind with craft drinks in a romantic setting and enjoy lively entertainment vibes throughout the evening.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Gloucester

Gloucester, Massachusetts, is perfect for beach lovers and outdoor enthusiasts, offering a blend of scenic beauty and rich history. Key attractions include the Gloucester Cathedral, Gloucester Docks, and the vibrant Gloucester Quays. Visitors can enjoy the local parks and explore historic houses and museums, making it an ideal destination for those seeking culture and relaxation by the sea.

  • Long Beach: Experience the quintessential beach vibes at Long Beach, located 4.8km from Gloucester. This beautiful stretch of sand offers a perfect spot for sunbathing, swimming, and beachcombing, ensuring a relaxing day by the sea.
  • Peabody Essex Museum: Immerse yourself in culture at the Peabody Essex Museum, situated 14.8km away. This renowned art museum features an impressive collection of Asian art, maritime artifacts, and American decorative arts, making it a cultural treasure trove.
  • Cape Ann: Discover stunning scenery at Cape Ann, located 6.4km from Gloucester. This picturesque cape boasts rugged coastlines, charming fishing villages, and scenic beaches, offering ample opportunities for exploration and relaxation.

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.

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

  • 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 Holiday

The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester holiday. 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 holiday homes are another top choice for people planning a holiday 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 holiday deals, you can see more impressive attractions like these.

Top hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

141 Essex Avenue Gloucester MA
S$300
11 Aug - 12 Aug
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"Room was clean and comfortable with a nice view. My only gripe was having no iron and board for ironing clothes before going out. We didn't have breakfast so i really don't know how that would have gone. I liked the location being close to downtown. Staff was awesome."

Reviewed on 5 Aug, 2026

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
S$596
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (996 reviews)
"Absolutely beautifully decorated, clean and we felt like we were on a resort especially with the pool on the roof top with a bar and music."

Reviewed on 6 Aug, 2026

Beauport Hotel Gloucester
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

107 Atlantic Rd Gloucester MA
S$439
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (854 reviews)
"Great views, clean, comfortable bed, modern furniture, balcony facing the ocean."

Reviewed on 26 Jul, 2026

Ocean House Hotel at Bass Rocks
See all 1,811 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.

Stay near popular Gloucester attractions

A rocky shoreline with large boulders and calm water.

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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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)
Stroll along Good Harbour 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 stone archway with a view of the sea.

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 artefacts while enjoying dramatic ocean views.
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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 holiday is part of your travel plans, Half Moon Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.
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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 through the beautiful beaches and seaside in this family-friendly 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)
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 harbour aboard the traditional Schooner Ardelle.
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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 in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
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Capt Bill & Sons Whale Watch

8.2/10 (12 reviews)
You can learn about the history of Gloucester with a stop at Capt Bill & Sons Whale Watch. Wander the seaside and beautiful beaches in the area.
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What to do in Gloucester

Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

S$28
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

S$22
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Freedom Trail and Salem and The Witch Trail Self-Guided Walking Tour Bundle

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

S$32
per traveller
100% of travellers recommend
Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester holiday package cost?
Offering great value package deals from S$801 on Expedia, you'll be thrilled with how little a holiday to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Gloucester holiday packages and you could score some excellent off-season deals.
How many days is enough for Gloucester?
Typically, a few days is great for a Gloucester holiday. With a well-organised schedule, you can check out all the best sights such as Cressy Beach, as well as explore some hidden treasures along the way.
Is it worth booking a holiday package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester holiday on a high note by exploring major attractions like Capt Bill & Sons Whale Watch.
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 holiday package as soon as possible.
Is it cheaper to book a Gloucester holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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?
  1. Choose your dates: What you'd like to do in Gloucester and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Gloucester.
  3. Decide how long to go away for: Now that you're up to speed on Gloucester, you can figure out the perfect length of your break. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.